Rational Bureau of Standards

-*. library. K.W. Bldg

MAY A 1961

PB 161586

^ecltnlcal ^2<?te 85

A SURVEY OF COMPUTER PROGRAMS

FOR CHEMICAL INFORMATION SEARCHING

U. S. DEPARTMENT OF COMMERCE

NATIONAL BUREAU OF STANDARDS
THE NATIONAL BUREAU OF STANDARDS

Functions and Activities

The functions of the National Bureau of Standards are set forth in the Act of Congress, March

3, 1901, as amended by Congress in Public Law 619, 1950. These include the development and

maintenance of the national standards of measurement and the provision of means and methods for making measurements consistent with these standards; the determination of physical constants and

properties of materials; the development of methods and instruments for testing materials, devices,

and structures; advisory services to government agencies on scientific and technical problems; in- vention and development of devices to serve special needs of the Government; and the development

of standard practices, codes, and specifications. The work includes basic and applied research,

development, engineering, instrumentation, testing, evaluation, calibration services, and various

consultation and information services. Research projects are also performed for other government

agencies when the work relates to and supplements the basic program of the Bureau or when the

Bureau's unique competence is required. The scope of activities is suggested by the listing of

divisions and sections on the inside of the back cover.

Publications

The results of the Bureau's work take the form of either actual equipment and devices or published papers. These papers appear either in the Bureau's own series of publications or in the journals

of professional and scientific societies. The Bureau itself publishes three periodicals available from

the. Government Printing Office: The Journal of Research, published in four separate sections,

presents complete scientific and technical papers; the Technical News Bulletin presents summary

and preliminary reports on work in progress; and Basic Radio Propagation Predictions provides

data for determining the best frequencies to use for radio communications throughout the world.

There are also five series of nonperiodical publications: Monographs, Applied Mathematics Series,

Handbooks, Miscellaneous Publications, and Technical Notes. Information on the Bureau's publications can be found in NBS Circular 460, Publications of the

National Bureau of Standards ($1.25) and its Supplement ($1.50), available from the Superintendent

of Documents, Government Printing Office, Washington 25, D.C.
NATIONAL BUREAU OF STANDARDS

technical ^Vtcte

85

FEBRUARY 1961

A SURVEY OF COMPUTER PROGRAMS

FOR CHEMICAL INFORMATION SEARCHING

Ethel C. Marden and Herbert R. Koller

NBS Technical Notes are designed to supplement the Bureau's regular publications program. They provide a means for making available scientific data that are of transient or limited interest. Technical Notes may be

listed or referred to in the open literature. They are for sale by the Office of Technical Services, U. S. Department of Commerce, Washington 25, D. C.

DISTRIBUTED BY

UNITED STATES DEPARTMENT OF COMMERCE

OFFICE OF TECHNICAL SERVICES

WASHINGTON 25, D. C.

Price $2.25

TABLE OF CONTENTS

ABSTRACT

INTRODUCTION

Page

iv

Notation for Chemical Structures 2

Indexes and Abstracts 5

Punched Card Systems 9

Special Equipment for Literature Searching ,13

COMPUTER SYSTEMS 24

The Dow Chemical Company 24

Midwest Research Institute (MTI) 27

Monsanto Chemical Company 31

Ray and Kirsch Work at NBS 34

HAYSTAQ 36

Use of the RAMAC-305 41

Report Searching on the Bendix G-15D at du Pont 43

Thermophysical Properties Research Center

(Purdue University) 44

Fine Chemical Service (England) 46

Farbwerke Hoechst AG 46

Badische Anilin und Soda Fabrik AG 47

Gmelin Institute 48

DIFFICULTIES, LINGUISTIC AND OTHER 49

CONCLUDING STATEMENT 58

BIBLIOGRAPHY 59-84

-in-
ABSTRACT

The authors describe twelve computer systems for

searching chemical literature. Preceding discussion of

the computer systems, a brief description is given of

different chemical notation systems, indexing and

abstracting procedures, punched card systems (which

were the forerunners of the computer systems), and

special purpose literature searching machines. A short

discussion of the difficulties (linguistic and other) attendant

to literature searching terminates the paper.

-IV-
A SURVEY OF COMPUTER PROGRAMS FOR CHEMICAL

INFORMATION SEARCHING

by

Ethel Marden and Herbert R. Koller

INTRODUCTION

Chemists, more than anyone else, have been concerned with the

need for mechanical aids to literature searching. They have evidenced

their interest by the publicity given over the years in their literature to

the efforts made in the notation, indexing, and abstracting areas and,

in later years, to the various projects for literature searching by

means of punched card machines, special purpose machines of several

categories, and computers. Workers in the chemical area have been

made aware of the need for mechanical aids because the chemical

literature has been increasing at a more rapid pace than most of the

other technological literature, in an era which has seen an explosion

of technical publications in all fields. Chemists particularly have been

aware of some of the problems which are encountered in setting up

systems for mechanical literature searching, which range from those of

a linguistic nature, through orientation of the planned-for system to the

specific objective desired, to considerations of requisite equipment.

They have sought solutions, both by encouraging the attempts of others

and, in some cases, by giving up their own professional careers in the

field of chemistry to join the workers in the area of documentation.

Recognition was recently taken by a Senate Committee of the

importance of scientific information retrieval, with its allied

problems in related areas. Among the interested organizations which

supplied testimony to the Committee on Government Operations of the

U.S. Senate were several chemical companies, who described their

work with chemical searching operations. In addition, the testimony

of others reflected some applications in the field of chemistry. For
a timely account of the status of scientific information retrieval work

in all areas, the reader is referred to the report of the Committee's

. 167/

• hearings. '

The terminology among information retrieval workers has not

been standardized, which leads to some difficulty in appraising the

content of the literature which has been published on this subject. (In

this report, for the most part, the language of the authors of papers

described has been preserved; this procedure naturally results in a

certain lack of uniformity in the present work. ) Several projects have

attempted to do something about the lack of standardization, among them

the American Standards Association, the Western Reserve University

Conference Committee, and, to a lesser extent, the UNESCO and IFIPS

groups interested in information retrieval.

The scope of the present survey is limited to the searching of

chemical literature and stored chemical information by general purpose

electronic computers.* There are quite a few computer projects

actively under way at this time. However, before the present stage of

development of literature searching in this area was reached, a great

deal of pioneering effort had to be expended in several fields tangential

to machine searching, and it is desired to give recognition to some of

this work.

Notation for Chemical Structures

Ten years and more ago, several independent groups proposed

notation and coding systems for the representation of chemical

17/ 18/

structures. '' ' As early as 1946 Dyson discussed a chemical

40/ ' cipher notation, ' and published a revised version of the original

system in 1947. —' Also in 1947, M. Gordon, C. E. Kendall, and

W. H. T. Davison proposed use of the chemical ciphering notation

65/

system, which came to be known as the "GKD Notation".- ' Most such

notation schemes were developed as a means of designating structures

in an unambiguous way without resorting to structural formulas, and as

No attempt has been made to include in the survey the classified

literature with respect to chemical literature searching.

-2-
a means of developing an alphabetical index for the structures. Although

the principal purpose was not to assist in mechanical aids to searching*

at least three of the early schemes were said to be applicable to such

mechanical searching, and appeared to be directed primarily to punched

card systems, though mention was sometimes made of the possibility

of use of computers for such applications. In fact, a special purpose

computer, to be used in conjunction with a card sorter, was actually

37/ proposed by the Gordon-Kendall -Davison group, - in connection with

their system of chemical ciphering. Specifications for this computer,

to be called the Electronic Structural Correlator (ESC), were described,

36/

but a prototype model was never built. ' Another pioneering effort

51/ was the numerical designation code developed by Frear, et al. ' The

basic principles of the Frear code were adopted as the nucleus of the

notation scheme used by the Chemical -Biological Coordination Center

25/ (CBCC) of the National Research Council, Washington, D. C. These

early activities were followed shortly by notation and coding systems

proposed by W. Gruber,.r. 21/ J

' J. G. Cockburn, with the Newcastle

34/ 157/ 192/ System, ' J. A. Silk, ' and W. J. Wiswesser. ' In the early

1950's, the National Research Council conducted extensive tests of the

notation systems proposed by Dyson, Gruber, Wiswesser, and Silk.

Based on the conclusions reached by NRC as a result of these tests,

E. M. Crane and M. M. Berry developed a composite notation system

which, in part, combined the best features of the systems tested by

NRC. They proposed use of a "classification code" as well as a basic

18/ structural cipher. ' In 1957, Wheeler, Andrews, Fallon, Krueger,

Palopoli and Schumann, from the Wm. S. Merrell Co. , Cincinnati,

Ohio, published a simpler code designed for an 80 -column punched card

187/ machine. ' They assigned a unique serial number to each compound,

and provided space to accommodate as many as 999, 999 compounds.

A modified version of the Wiswesser notation has been used by

Elbert G. Smith, at the University of Hawaii in Honolulu, * for search159/

ing a catalogue of 50, 000 compounds in a punched card operation.

Now at Mills College, Oakland, California.

-3-
Several more notation schemes for chemical structures have been

proposed in recent years, among them Isbell's system for carbohydrate

83/

structures, ' Luhn's system for identifying geometric patterns by

description of their envelopes, ' Chodosch's ciphering system, - and Feldman's stereo numbers. 46/

In connection with plans for mechanized searching, a group at

VINITI (the All-Union Institute for Scientific and Technical Information,

Moscow) is working on a notational coding scheme for structural

configurations. Since there is considerable interest in correlating

physical or chemical characteristics with structural features, the

coding is directed to only that part of the total configuration which gives

rise to the property of interest. The system is said to be "simple and

rational, " and, while longer than, for example, the Dyson notation, it

is claimed that it is more logical than the Dyson system. It is also

claimed that it will be applicable to subject matter in mathematics,

linguistics and physics, as well as chemistry. '' '

Another system of notation, developed by a group at the Moscow

State University under Professor A. P. Terentiev, called the TKZP

system (Terentiev, Kost, Zuckermann and Potapov), is designed to

record both the spatial configuration and the connectivities of the various

atoms or groups of atoms in the structure. In a paper describing this

system, the authors also propose a scheme for v causing a machine to

convert a formula or compound name to an atom-by-atom recording,

197/ 93/ formula, or code, without manual aid. ' Kent et al ' also report

(see footnote 7 of the Kent et al paper) that this group of workers is

129/ 125/

developing codes similar to those of Opler and Norton ' ' for

use with computers.

Vleduts, in a long monograph on notation, indexing, and nomenclature, discusses the Dyson system and compares it extensively

with the systems proposed by the VINITI group and another proposed

1 line;

172/

17 1/ Russian system. ' In another paper, he discusses a linear language

for organic chemistry suitable for machine searching.

-4-
A proposed international standard notation system .based upon the

Dyson notation, has been recently published by the International Union

82/

of Pure and Applied Chemistry. '

By a fortuitous accident, or by inspired foresight, some of the

work on notation systems anticipated some of the major considerations

in devising systems for computer searching. One of the principal and

continuing investigations facing would-be machine searchers is that of

linguistics. Certainly the early notation schemes resulted in symbols

which offer a working intermediate stage between English language text

and machine language in the representation of chemical compounds. It

is not intended to imply in any way that the linguistics problems have

been solved, even in the area of chemistry, but only to state that a

basis has been formed for the conducting of simple machine searches,

on limited size libraries or catalogues of compounds. The topological

nature of the structure was also recognized by the early devisers of

structure codes, and groups were represented in some codes with bonds

indicated, in others not. Even in cases where no direct use was made

of any one notation system, the thinking which led to devising the

systems, on some of which several years were spent, has formed a

springboard for further exploration. The work which has gone into

them has undoubtedly influenced the thinking of every person who is

engaged in setting up systems for chemical literature searching.

Indexes and Abstracts

The abstracting and indexing services have formed two of the

most important aspects of information retrieval, both before and after

the rise of computers in this field. Abstracts make available to the

scientist much more information than he would be able to scan otherwise; indexes give him his best route to the recovery of information.

Because of the recognized importance of the work in these two areas,

there has been widespread activity in both abstracting and indexing in

this country and abroad. It is impossible to give credit here to the

fine work accomplished by many devoted scientific personnel working

in these two areas.

-5-
Eugene Garfield, who has been diligent in the indexing area of

information retrieval, made the statement that "The abstracts section

of Chemical Abstracts is a device for dissemination while the index is

58 /

for retrieval. " —' Welt has combined the two, which results in a "lengthy hybridized index entry, " and has used such an index for the

handling of 13, 000 (in May 1958) papers, in diverse languages, in the

183/ Cardiovascular Literature Project of the National Research Council. '

Although Chemical Abstracts does a monumental job in summarizing the chemical literature, many large problems still reside in

supplying service of this type and scope. The importance of continuing

research in these areas was recognized by the recent International

Conference on Scientific Information, which devoted one of its seven

79/ areas to indexing and abstracting problems. —' It is important to note

the accomplishments in these areas, both for the purpose of evaluating

the applicability of the methods used to machine procedures, and (more

important) for the purpose of making firm decisions to deviate from

them for mechanized practices, where necessary to do so. If recovery

of all information is required, abstracting becomes a very much more

difficult procedure. It is at once more selective and more inclusive.

Information not particularly pertinent to the main body of the article

being abstracted may increase in value tremendously when evaluated

in a different context, or it may increase in significance because of

new developments. Computer systems tend to make multi -branched and

greatly expanded usages of stored file data, which are usually not

anticipated to the fullest extent when such files are prepared. For such

purposes, abstracts which represent summaries may not be all-inclusive

enough for mechanized systems. A pursuit of this reasoning reveals

that only a multi -level indexing which lists every subject will be

adequate.

Various indexing proposals have been made for chemical

literature. Bernier proposes that, using techniques of alphabetical

correlative trope indexing, arbitrary symbols or names be used to index

organic groups, ' to form a "correlative chemical-group index. " Among the proposals that have been put into operation is the one which

-6-
the American Society for Metals and the Special Libraries Association,

working together, have developed. This is an indexing and classification system known as the ASM-SLA classification for edge -punch cards

which covers not only the field of metallurgy, but various aspects of

metallurgy found in the areas of chemistry, physics, and

3/, 50/, 90/ A

. . , , engineering.—' A computer analysis of an indexing system

for 40, 000 documents has been made by Remington-Rand, with

particular interest given to the number of descriptors used to describe

documents, frequency of use of descriptors, combining power of

a «- 152 / descriptors, etc.

Citation indexes have been proposed by Eugene Garfield both

59/ in the area of chemical patents ' and for other scientific

literature —'

' -, where the index would be accumulated and oriented

to the user's frame -of -reference. On the other hand, for quickly

supplying users of information with knowledge of current developments

in their field, as an alternative to abstracting services, Garfield

supplies photocopies of the contents pages of all current periodicals in

their particular area of interest. These are sometimes made available

by the journal publishers prior to actual publication of the journal.— —

The task of analyzing a document and extracting from it the

significant portions to be included in an abstract or a file is a very

demanding one, and normally requires the skill, knowledge, and

experience of technical personnel. Experiments in delegating this task

to computers have been tried by H. P. Luhn of IBM, who employs

statistical procedures on the IBM 704 to extract sets of significant

words, based on the frequency of their occurrence within a

document. • ' Planning Research Corporation's experimental

studies in automatic indexing and abstracting have employed the

"relative -frequency approach" to the measurement of the significance

of words, word groups, and sentences; they use the frequency of both

"uniterms" and "multiterms" as a function for the production of "autoindexes", and multiterms for the production of "auto -abstracts". As

in Luhn's work, the auto -abstracts take the form of "extracts" from the

43/ author's own language. ' Similar auto -abstracting work is being

-7-
carried on by V. A. Agrayev and V. V. Borodin (Gorkey). —' General

purpose computers or "information and translation machines" can be

used for the work. Only significant words are taken into account; tests

of several methods are based on (a) frequency of occurrence of words

and (b) probability of reciprocal combinations of words within a sentence. As a result of analysis of inflections during the summarizing

procedure, some of the more significant sentences are isolated from

the text. Indexing, largely as related to notation and nomenclature

schemes proposed by Dyson and certain Russian workers, is discussed

1 *7 1 /

at some length in a monograph by Vleduts. '

Ohlman (of Systems Development Corporation) and Luhn have also

accumulated bibliographies by "permutation indexing" (Ohlman) or

"key words -in-context" (Luhn) experiments, using direct computer

output for the bibliographies. ' ' '

' ' In this connection,

Chemical Abstracts is initiating the publication of a bimonthly serial

publication of a permuted title index from, in the beginning, some of

the 8000 journals received in their office each year, which includes,

in addition, the list of titles, authors, and references. (* ' A

bibliography of papers on the subject of permutation indexing going

127/ back as far as 1856 has been compiled by Ohlman. '

As an aid to indexing, Eugene Wall, of the Engineering Service

Division of du Pont, has been concerned for several years with the

arrangement, grouping, and indexing of material making up a store.

He believes that more effective indexing will materially assist in

recovering information which has relatively few "handles" for

retrieval, and he proposes that the indexer be provided with reminder

lists of words generally associated in context with those used in the

text. He calls such a list a "Word-association Matrix";—'

' '

this matrix consists of a list of associated terms, listed in order of

frequency of association under the main term, and could be considered

in this light a coordinate indexing arrangement.

See also discussion under DIFFICULTIES, LINGUISTIC AND

OTHER.
There will be available next year an A. I. Ch. E. Thesaurus, based

on one which the du Pont Company has for internal use, but modified

and enlarged from that version. In addition, the Institute publications

will incorporate new style abstracts and indexing terms for each

article in each issue, for easier use of the Thesaurus. This work was

44/ done under the auspices of the Standards Committee. —

Punched Card Systems

Although the principal content of this report is not concerned

with punched card systems per se, it is interesting to note the effect

of some such systems on the development of electronic computer

systems. In some cases, punched card systems were the forerunners

of similar computer systems, and some projects, with added

sophistications in some cases, were transferred from punched card

equipment to computer installations, without a complete transformation

in the systems. In these cases, the punched card systems were

simply the forerunners of the computer programs, but they determined

or defined in some cases the directions taken by their successors,

which were handled by computers.

Many systems lend themselves successfully to handling by

punched card equipment, and for that reason are still carried on by

such machines. In some cases, an electronic computer could speed

up the search, but otherwise could add little to the advancement of the

caliber of the program now in existence. Indeed, in some instances

where random access and variable branching are not involved, punched

card systems are superior because of the capability of executing

parallel searching on punched cards. Because of the decision-making

ability of punched card equipment at the time of input of the card, this

kind of system can be faster than computer operation of a similar

nature, in cases where this kind of operation is particularly suitable.

Where punched card equipment is suitable for the particular application,

punched card operation is generally considerably cheaper, both in

terms of equipment needed and in kinds and numbers of personnel

required.

-9-
The U.S. Patent Office makes prior art searches by means of a punched card system in connection with patent applications directed

52/

to steroid compounds and their synthesis. —' The cyclopentanohydrophenanthrene nucleus is assumed to be present in each structure

and the coded description of each compound is recorded on one card.

Twenty -two substitution positions are provided for; at each of these

points on the basic structure may be found any one of nineteen common

types of substituents, double bonds, alpha or alio configurations, or

miscellaneous groups. Each such substituent and position has a

specific punching position in one of the columns 1 to 48 on an IBM card.

In columns 60 to 69 are recorded general descriptors not identifiable

with any particular position on the nucleus. Searches are made

serially on a multi-column sorter, although a single column sorting

machine may be used.

For the purpose of testing the relative efficiencies of such a serial file and an inverted file, a group of workers at Documentation,

Inc. , converted the codes for the same steroid documents into an

inverted file on Matrex cards, and made some comparative studies of

the relative searching efficiencies.

Much of the information retrieval research being carried on at

universities makes use of punched card equipment; this is true of some

of the Groth Institute work being carried on at The Pennsylvania State

University in connection with chemical and physical data on

crystals; —' ' ' ' 'and the work on properties of hydrocarbons

2/ and related compounds at Carnegie Institute of Technology. —

Using the Wiswesser notation, a punched card process for recording

and recovering chemical information was described at Remington-Rand

14/ 126/

as long ago as 1953. —' Chemical companies, such as Dow,

182/ 49/ 42/

Ethyl Corporation, ' American Cyanamid, — and du Pont, — of

course, made early use of punched card equipment for searching for

chemical compounds, as did pharmaceutical companies such as The

151/ Sharpe and Dohme Company, ' (now the Merck, Sharpe and Dohme

144/ Research Laboratories) and Smith, Kline, and French. Linde

Company links chemical terms to "role indicators", and calls such

-10-
combinations "structerms;" there is a dictionary or glossary of such

186/ terms, together with the role the term plays in the context. - Linkage of the documents with the structerms is by means of the cards

themselves, which are known as "docuterm cards". The punched cards,

dealing with internal technical reports, principally chemical laboratory

reports, are collated for the structerms, which include role indicators.

The Chemical Department, Experiment Station, of the E.I. du Pont de

Nemours and Company, has a punched card system for the indexing of

chemical compounds and polymers, where the card for each compound

and polymer component carries additional information, such as types of

4- 42 / reaction, properties, etc. —

An important early contribution to information retrieval was

made by the Chemical -Biological Coordination Center, who devised a system for searching chemical and biological literature in such a way

as to correlate the chemical and biological characteristics of such

193/ material in the files. - There were several outgrowths as a result

of the early pioneering work of the CBCC (some of which are now

developing into computer programs). Among them was the work of

Maloney, at Fort Detrick, who developed a medical and chemical

113/ system patterned after the CBCC work. ' Welt developed one of the

CBCC ramifications, which has subsequently become the Cardiovascular Literature Project. A somewhat related project

dealing with carcinogenic effects of chemical compounds is being

carried on at the Cancer Chemotherapy National Service Center at the

56/ National Institutes of Health in Bethesda. —

Smith, Kline and French Laboratories have also developed a

system in which biological effects are correlated with characteristics

133/

of the materials that cause them. ' They have made syntactical and

semantic studies, and from these analyses have developed a simplified

grammar with rigid rules of word order for expression of information

for machine indexing. The area of use is in the fields of biology,

chemistry, and clinical medicine. Although the work is being conducted

on an IBM 101, the logic of the system has been developed with

application to electronic computers in mind; and Smith, Kline and

11-
French apparently expect to employ computers for the work sometime

in the future, according to their statements.

The Netherlands Patent Office (Octrooiraad) is engaged in

experimental work on a retrieval system for documents which deal with

95/ carburetors for internal combustion engines. —' The fluid employed in

the carburetor is an integral part of the procedure, and for this reason

the work has interest for chemists as well as engineers. Approximately

16, 000 documents are in the collection under study. Coding of

characteristics is done on horizontal rows of conventional 80 -column

punched cards; relationships between characteristics are shown by

interfix punches in columns 48 to 59. Each characteristic is

represented by a series of characters, each containing four binary bits.

One character specifies the main aspect (e.g. , cooling device, mixing

device, throttle); up to four characters specify details of the

characteristic; and one character denotes the type of fluid which is

flowing through the carburetor element being described. The system is

suitable for use on a machine such as the ILAS, of the U. S. Patent

Office.

Dr. J. M. Ganeff, of the Institut International des Brevets (The

Hague), is experimenting with an internally slotted card system for

57/ searching documents dealing with electroluminescent materials. —' A special device has been developed to agitate the deck of cards to

permit those with slots in needled positions to drop and to be separated

from the rest of the deck. Each card represents one document and each

slot represents one characteristic or category on a classified list of

topics of interest in this field. The subject matter is characterized

from many points of view.

Most punched card systems for searching in the area of chemical

applications seem to serve the specialized needs of those who instituted

the systems. There have been few, if any, large-scale generalized

punched-card systems developed which would be all-encompassing

enough to serve the common need of all users of mechanized equipment

for searching of chemical literature. Among the few systems which

sought to embrace a larger territory was that developed by the

-12-
U. S. Patent Office, —' and it was motivated in this by the necessity

of making many kinds of searches of large and heterogeneous files.

For a number of years, the Australian Patent Office has been

searching applications by means of a punched card system. It is not

in the province of this paper to report on all such punched card

systems. However, there have been two editions published of an

excellent work by Casey, et al, which do present a much greater

. ., . 23/, 24/

coverage in this area. —' —

Special Equipment for Literature Searching

Commercially available machines specifically designed as

literature searching machines have not yet come into widespread use. This is not surprising, since there is no general agreement on the

form of data for storage or on searching systems design, nor have

there been developed any really satisfactory comprehensive general

theories which can explain, correlate or predict the characteristics

of such systems. —

For the most part, mechanized searching schemes that are in

actual use have employed general purpose machines or machines

12 1/ designed primarily to perform other types of tasks. ' Some

writers have discussed characteristics which would be desirable in

information retrieval machines and have shown why general purpose

97/ machines are probably not "the answer. " —' It should be stated,

though, that strong arguments have been advanced in support of the use

of general purpose computers, at least until such time as there is

128 / developed better information about user requirements. However,

a number of proposals for information retrieval machines have been

made and these will be described briefly below. It is not known how

many of these machines have been used for chemical literature

searching, but it is possible that any one of them has been, and all

certainly have the potential. It was therefore decided to include a

fairly comprehensive list of them for their possible interest to the

reader.

-13-
Probably the most widely known proposal for a mechanized

21/ information retrieval system is the MEMEX of Dr. Vannevar Bush. -—

Dr. Bush's early contributions in this field are well known, both his

work on the Rapid Selector —'' '' -^ and as Chairman of the

Advisory Committee on Application of Machines to Patent Office

Operations; ' his thinking has been an inspiration to many later

workers in the field.

Edge notched cards have been used by a large number of groups

in retrieval applications; specialized equipment for use with this type

of card has been developed by several organizations. A good review of

available equipment is given by Casey et al. — —

Equipment for implementing the type of searching system which

is known in this country as the "Peek-a-Boo" system has been designed

by and is in use at the National Bureau of Standards. ' ' ' Commercial equipment intended for use with peek-a-boo cards is sold

under the names TERMATREX or MATREX. —'

Punched card sorting machines (IBM type cards) have also been

built especially for information retrieval purposes. The ILAS machine,

developed at the U. S. Patent Office, provides facilities for searching

hexadecimal codes recorded on the horizontal rows of an 80 -column

punched card and for relating codes to each other by grouping signals,

interfixes and modulants. —' A storage and retrieval scheme for use

54/ with this machine has been developed by the Patent Office. —' The

system has been applied to documents dealing with ethylenic unsaturated

homopolymers and copolymers. The information content of each

document is recorded on punched cards, compounds being identified by

unique numbers and classes of compounds being similarly identified.

Functions of compounds are recorded as "modulants" or modifiers of

the subject matter (compound) codes. Relationships between the several

codes for a compound, between the several compounds associated

together in a process, and between all of the codes in a document, are

denoted by grouping signals which follow the last code of the group

involved. Interfixes are used to show relationships among the various

groups. By assigning "weights" to the parts of a question and

-14-
specifying a minimum total weight for acceptable answers, it is

possible to retrieve documents which fully meet the search criteria as well as those which meet them only partially. It is possible to

search for compounds, functions, and processes.

In collaboration with the Textile Fibers Department of du Pont,

this system has also been experimentally programmed for the Bendix

54/* G-15D computer. —' The information is recorded in two types of

words, one of which includes modulants and subject matter codes, the

other interfixes and grouping signals. One more character in words

of the first -mentioned type is added for questions. This character indicates to the computer whether or not modulants are being searched,

and whether the subject matter codes are to be matched on an equality

or an "included in" basis. The output is a printed table which states

whether or not the full "weight" or the minimum "weight" of the

question has been achieved, whether all subjects and interfixes

required have been found, and whether all specified relationships

were found.

The International Business Machines Corporation offers the 9900

Special Index Analyzer, which is a form of collator for performing

coordinate indexing searches. ' For the 9900, IBM cards are

punched, one for each term in a glossary, with codes for the documents

to which that term applies being punched on the card. Decks of cards

are operated upon to find sets of documents representing, for example,

the logical union, intersection or intersection with complement, and

the results are automatically typed. Searching systems designed for

use with this machine have been developed by M. Taube. '

The Row-by-Row Scanning attachment is a device which permits

the IBM ESM-101 to analyze a pattern represented within a single row

of a card, independently from patterns in other rows, and of storing

the incidence of a match until all 12 rows of a card have been analyzed

in a similar fashion. ' The 101 with the scanning attachment may

This work is discussed in greater detail under COMPUTER

SYSTEMS.

-15-
also be programmed to detect given patterns in predetermined rows, or

to determine that certain patterns precede others (in the order they are

found amongst the various rows). These variations from the normal

behavior of the 101 are produced by changing the functions of some of

the recode selectors. A large variety of coding schemes are possible

for row coding, as contrasted with the more conventional Hollerith

column codes, fixed field, or superposed random codes. It is of

interest to note that a 101 was specially modified to operate in this

manner for the Patent Office in 1950. —

'

The IBM 9310 Universal Card Scanner is a later development of

the type of machine represented by the earlier X-794 and "Luhn

Scanner" machines, which used as one example Dyson's System of

Notation of Organic Compounds in a demonstration of the machine.

For these machines a code in a file card is punched on a vertical

column, with each permissible code being represented by a pattern of

exactly five punches. Questions are asked by means of cards in which

the 7 -hole complements of the desired codes are punched. Matching

is done by an optical "blackout" technique; coincidence between a file

code and its complementary question code indicates a match. Thus,

holes in file codes must all match "no holes" in the question codes, and

110/ vice versa. ' 92/ The WRU Searching Selector, —'which uses relays internally and

has a punched paper tape input, was developed at Western Reserve

University. Questions are entered through a special typewriter, and

the file, which is stored on the tape, is read into the machine for

comparison with the stored question. A number of searches can be

made simultaneously. The subject matter logic employed permits use

of a number of levels of grouping of information, such as words which

are contained in sentences, sentences which are contained in

paragraphs, etc. A number of other relationships, such as "negation,"

"AND, " and "OR, " may be indicated, as well as ranges of numerical

information. Output is by typewriter. This equipment is being used

at Western Reserve University in connection with the metals

information service conducted there, as well as with other projects at

-16-
143/ WRU. ' Several existing general purpose computers have been

programmed to perform searches of the types being made on the "WRU

89/ Searching Selector; —' these include the IBM 650 and 709 machines.

Information to be searched by the WRU system has also been prepared

in a format which will make it acceptable to the Minicard system.

General Electric initiated a transistorized version of the WRU machine,

72/

the General Electric Information Searching Selector (GE-2 50), — with

a magnetic tape input. However, by mutual agreement between GE and

WRU, a general purpose computer, the GE-225, which embodies the

searching characteristics of the GE-250 in addition to the potential of a computer, was substituted to replace the GE-250, which was not put

, .. 63/, 88/

into production. —' —

For the purpose of maintaining U.S. Air Force personnel files for

more than 1. 5 million individuals, an auxiliary special purpose machine,

the GE-260 High Density Information Selector, has been proposed for

use in conjunction with a computer. The principal distinguishing

characteristic of the GE-260 is a thermoplastic tape memory for

storage of the 1. 5 million personnel records, where it is expected that

each personnel record will contain approximately 1000 characters.

Four simultaneous searches can be performed, with a search time of

64/ under 20 minutes. —'There are two modes of operation: (1) under

program control of the computer and (2) by means of inquiries put

directly to the "inquiry buffer", which has a capacity of 288 characters.

Results may be obtained by means of an electric typewriter.

Computer Control Company has designed and built the Index

94/ Searcher for the Rome Air Development Center. —' This machine

stores the file to be searched on magnetic tape. Questions may specify

up to ten criteria for search and the elements of the question may be

grouped into as many as 15 phrases by plugboard wiring. The machine

can be operated in any of six different modes, identified as document

search, regenerate tape, question insert, search, print, and (tape)

edit. 5200 words, each containing 42 bits, can be scanned per second.

The average document is encoded in 20 words, about 68, 500 documents

being storable on a 2400 -foot reel of tape; about 260 documents can be

searched in one second.

-17-
188/ The Magnacard System, of the Magnavox Company, '- while not

specifically designed for information retrieval purposes, is a

sufficiently interesting data handling device to require mention here.

Characteristics of the system suggest its use for searching by employing

the sorting and file -manipulation facilities that it offers, as well as its

potential use as a computer input device. Magnacards are l"x3"

magnetic oxide coated mylar cards, each capable of storing over 5,000

bits. The cards are made to adhere to transport drums by a pneumatic

system, which has the effect of converting the transport drums into

magnetic drums. Magnetic reading heads are provided for sensing the

coded data.

Several machines have been devised for retrieval purposes which

make use of photographic storage elements. In each of them, frames

of film are presented to a reading station at which binary coded

information is sensed; each frame contains both photographically

recorded pages of documents and binary codes describing their contents.

Upon recognition of the desired code factors, an image of the pictorial

part of that frame is projected for viewing or copying. The Minicard

system of the Eastman Kodak Company employs discrete pieces of film

which are manipulated in a manner similar to the handling of punched

99/ cards. —' The relative amounts of space devoted to pictorial and coded

information are completely flexible. The Filmorex System is generally

similar; however, one difference is that the pictorial and coded areas

15/, 194/

32/ 145/

are fixed. —'

' • Both FLIP (Film Library Instantaneous

Presentation), a product of the Benson-Lehner Corporation,

and the Rapid Selector employ continuous reels of film. The Rapid

Selector was first constructed by Vannevar Bush, but ideas concerning

it were previously discussed by many people (among others, Draeger and

Davis), both during and prior to its inception. Ralph Shaw was subsequently interested in its development; it was later improved by a group

at Yale and is at present being further developed at the National Bureau

of Standards for the Navy's Bureau of Ships. 2/' 111/' ±£2/> Hi'' IM/

The Minicard, Filmorex, FLIP, and Rapid Selector systems each sense

the coded patterns optically. A similar machine described by Peter

James of IBM uses as a file storage medium a photographic film

-18-
containing images of document pages adjacent to an alterable magnetic

strip on which are recorded the binary coded data descriptive of the

document. —'

An apparatus for performing coordinate indexing searches

137/ mechanically is described by Plankeel. ' Punched tapes are used

rather than the cards usually employed in this type of system. Each

document in the collection is assigned a number which occupies a unique

position on any tape which refers to an indexing term related to that

document; each tape represents a single indexing term. Every punching

position, starting at some fixed point on the tape, corresponds to a

single document number, and each channel on the tape represents a

different series of document numbers. A punch in any one position

signifies that the correspondingly numbered document contains the

concept of the indexing term to which that tape refers. Only those tapes

are searched whose indexing terms are required. The equipment

comparesthe pertinent tapes simultaneously for coincidences of punches

in corresponding positions, and automatically records the numbers of

the documents which "possess all the terms represented by the tapes. " A mechanism is also proposed for correlating such a searching

technique with a document copying device. In this form, the tape search

is correlated with a film strip which contains micro -images of

document pages. Recognition of an answer to the search question results

in the printing of enlarged photocopies of the documents found by the

system.

Each of the searching tools discussed so far requires some form

of physical movement of the file or motion by the machine used to

effectuate the search. The time required for making the search is

dependent upon the size of the file, or upon the length and complexity

of the question, or upon both of these factors. This may be attributable

to the fact that, in most cases, searching systems have been designed

for use with equipment designed for other purposes, such as punched

card machines and computers. Searching systems designed for use

with these more or less conventional types of machines have employed

various techniques to alleviate the time problems involved. Generally,

-19-
these have involved screening techniques or various attacks on the

file organization problem, both intended to preclude the necessity for

detailed inspection of all information in the file. Some systems which

resort to inspection of only some of the documents in the file are those

employing classified decks of punched cards, or classified tapes in

the case of conventional serial machines, or inverted files of either

the peek-a-boo type or the Patent Office's DRAM system. '- In

the HAYSTAQ system ' (which is a serial search on a stored

program digital computer), after an externally stored encoded

document is read into the internal storage it is "screened" by inspecting information which gives general information about the document

contents. If it is determined that there is no possibility of an answer,

details of the document are not examined. Another proposal is that

a serially inspected file be so organized that the "most likely"

documents are looked at first. None of these approaches completely

eliminates the defects inherent in systems having time span

characteristics resulting from the serial nature of the searching

operation.

A logical development, therefore, is the series of proposals

for systems and machines which employ a static file and interrogate

all portions of the file simultaneously. In effect a search question is

broadcast to all documents in the file at one time and those which

satisfy that question all respond simultaneously. A group at the

Benson-Lehner Corporation has proposed such a system and has

4- AU A * -4- 1 4- 4-- 62 A 181 A !95/ suggested hardware for its implementation. ' '

' The Sandia Corporation has also come forward with such a 114/ suggestion. Documentation, Inc. has designed the EDIAC, which

is a small model of a simultaneous searching machine. ' Some

requirements and advantages of this kind of development in automata

have also been discussed by groups at the Patent Office and the

97/ National Bureau of Standards. ' At least two devices are known which will locate microfilm

copies of documents in a file and project an image or reproduce it

photographically. Both of these require that the exact physical

-20-
location of the desired document be specified, and they should be

considered as a special form of retrieval equipment, but not as

searching machines. One of these is the automatic micro -image file

proposed by M. L. Kuder of the National Bureau of Standards. In this

system, up to 10, 000 miniature photo -images are recorded on a 10-

inch-square sheet of microfilm. When coordinates of desired images

are specified, the machine, operating continuously, photographically

prints out one frame every two seconds. — ' A further development

of this type of apparatus, called the VERAC 903, has been made by the

8 / 20 / Crosley Division of AVCO Corporation. — ' —

The second machine, AMFIS (Automatic Microfilm Information

System), stores images on 20" microfilm strips, a multiplicity of

which are contained in "scrolls". Access to these strips is obtained in a fashion comparable to sliding a hair comb out of its carrying case. A

number of such scrolls are mounted on the face of a drum. The address

of the desired document is dialed from a keyboard and access is

achieved by three simultaneous movements: movement of the drum

along its axis, rotation of the drum to locate the appropriate scroll, and

the unwinding of the scroll to position the desired area of film between

7/

a light source and an optical system for projection on a viewing screen. —'

One additional special-purpose machine which should be mentioned

is the FLEXINDEX of the I. H. and R. Co. —' The system is centered

about a coding device which takes common words entered from a keyboard and automatically encodes them in a greatly compressed form.

Searchable files made by use of this device are stored on magnetic

tapes and questions asked by specifying the pertinent terms via the

coding device.

While information concerning the development of information

storage and retrieval machines in the USSR has been somewhat

incomplete and sometimes conflicting, it is known that at least two

such machines have been built or are under development.

In 1954 the Institute of Scientific Information of the Academy of

Sciences (now known as VINITI, the Ail-Union Institute for Scientific

and Technical Information, headed by Prof. A. I. Mikhailov) produced

-21-
the Experimental Information -retrieving Machine, designated as the

EIM. This device operates upon punched cards which are divided into

four fields, each of which employs a distinctly different type of coding

system. The cards are the conventional 12 -row, 80 -column variety.

The first 25 columns are devoted to alphabetic and numeric information,

recorded in a manner similar to the well known Hollerith code. Columns

26 to 33, which include 96 punching positions, are directly coded, each

position representing a distinct characteristic of the document being

coded. Columns 34 to 40 contain random superposed codes. Columns

41 to 80 make use of the horizontal rows to record data, each row

containing eight characters made up of 5 bits each for numeric

information. By using columns 39 to 80 in this manner, 6 alphabetic

characters containing 7 bits each may be recorded on a row. The

horizontal code patterns in this part of the card are recognized by the

machine regardless of the row in which they appear. Questions are set

up by means of plug -board wiring and console switches. Cards are

scanned at the rate of 420 per minute. The comparison apparatus is

said to employ "cheap and reliable" elements, rather than electronic

valves or relays, while the apparatus for registration of the results

'Wioes comprise several electronic recording and relay elements. " A

special offline printer is provided for recording the bibliographical

information on cards selected by the search. ' ' ' 93/ A brief mention is made by Kent and Iberall —' of a special

purpose information machine being developed for the faculty of organic

chemistry at Moscow State University, scheduled for delivery in 1959.

No details of this machine are given by Kent et al and it is not certain

whether this equipment is different from either the EIM or the machine

described in the next paragraph.

An "information machine" which is apparently intended for

retrieval, translation, and other forms of non- conventional information

handling processes is under development at the Laboratory for Electric

Modeling in Moscow. This laboratory is a part of the Institute for

Precise Mechanics and Computational Techniques, which is also

attached to the Academy of Sciences. The machine development work

-22-
is-under the direction of Dr. L. I. Gutenmakher. The file of

information is recorded on sheets of paper about 7 l/2 x 14 inches in

size, on which are printed metallic spots which act as capacitors. A

pattern is recorded by punching out some of these spots. The sheets

are compressed into blocks or "books", and the pattern circuits on such

a collection of sheets are interconnected by bus bars. Interrogation of

the entire block is made simultaneously; no physical movement of the

file occurs during the searching operation. It is claimed that very

large volumes of information can be searched in a very short time, one

hour being required to search the equivalent of 4 million pages of

ordinary text. The storage responds to descriptors, rather than to

addresses, and the individual pages or books constitute, in effect, a 93/ 73/ 74/ non-addressable storage. —'

' —' ' —' Recent visitors to this

Laboratory have reported that a 100, 000 -bit capacitor storage is now in

operation and that this type of store is ready for production by

industry.

Vleduts et al have taken the position that "While general-purpose

computers are quite suitable for experimental work in this field,

specialized information machines are necessary to obtain serious

practical results. " He describes the machine memory recently

developed under the leadership of Prof. L. I. Gutenmakher, and states

that it is particularly suitable for chemical information searching,

since it makes it "possible to consider the creation of a large

informational-logical machine for information on chemical compounds

and chemical reactions. " He states further that in this connection, it

is possible to simulate certain aspects of "chemical thinking" to aid in

173/ methods of synthesizing compounds not yet produced.

28/ A brief report in Electronics —'mentions a special machine,

under development for the Council for Cybernetics of the Academy of

Sciences, which will perform chemical information retrieval tasks.

It is stated that the machine will use an algorithmic technique,

"translating chemical characteristics into mathematical expressions by

matrix inversion and other linear methods. "

-23
COMPUTER SYSTEMS

The authors have attempted to describe the major computer

chemical searching systems which have been developed, either on an

experimental basis or to be used as productive tools in research. No

distinction has been made between those which have been developed and

later abandoned, those which are quiescent, or those which are in

active operation; it is sometimes dangerous to make the distinction,

even when it is supplied by the originators of the systems, because the

status of such projects is subject to change, either in whole or in part.

The dormant stage of such work, as well as the more active stages,

sometimes contains valuable lessons for others. Information

concerning work which has not been described herein is invited.

The Dow Chemical Company

Ascher Opler*, together with Ted Norton, when at the Dow

Chemical Company, developed a topological system for coding and

125/ 129/ searching chemical structures. ' ' ' The earliest programs for

this system were written around 1952. Several commercially available

general purpose computers have been used in the course of the years

in this work, among them the Datatron, IBM 650, 701 and the 704, on

which the work has been performed exclusively since 1956. The file

included approximately 15, 000 structures, stored on magnetic tape.

The chemical groups which are coded are intermediate in size between

single atoms and very large general groups. Thus, the authors reject

the idea of coding the benzene ring as six single carbon atoms and also

the idea of coding benzoic acid as a single group. Something over

300 different structural groups are provided for in the code schedules,

each identified by a 3 -digit number. In coding a structure, each such

group is assigned seven digits. If group A is being coded, the first

digit identifies the position in a previously coded group (B) to which A

is attached. The second digit specifies the position of A which is

attached to B. The third, fourth, and fifth digits are the identification

5^ Now with Computer Usage Co. , Inc. , New York, New York.

-24-
of the A group. The sixth is a number arbitrarily assigned to group B

in this compound and the seventh is a similar arbitrary number

assigned to group A in this compound. Rules are provided for the

order of enumerating the code groups.

An example for the code of one such structure is as follows:

CH (CH3

) 2 -*—

D

B D

0110601 10512 1121123 5200324

106 = BENZENE

105 = CYCLOPENTADIENE

211 = HETERO -NH003 = PROPYL

061 = CHLORINE

3106115

In making a search, five criteria must be met, and failure to

meet any one terminates the search. The first test is for the empirical

formula, * and that of the compound being examined has to be at least

equal to the one requested. The second test is for the presence of the

groups specified by the question. These are called "keys". The third

test ascertains whether stated keys, taken in pairs, are indirectly

connected through a third group. The fourth test is for relative

The authors have attempted to employ the same terminology

used by the originators of the research being described; the use

of the term "empirical formula" in some instances and "molecular

formula" in others reflects this practice.

25-
positions of pairs of keys sought in the third test. The final test

determines whether stated pairs of keys are directly attached.

It is possible to ask for a class of groups, such as "alkyl",

rather than for a specific one, and such a search is satisfied by finding

a structure containing any one of the 30 or so specific alkyl groups

provided for in the schedule. The technique used here is a look-up

operation, in which the computer, after noting that "alkyl" is a class

term, refers to a stored list of specific groups which are of this type,

and, in effect, substitutes these specific terms for the generic term

used in the question. It is possible to perform up to five independent

searches simultaneously by a "multiplexing" technique. The output of

a multiplexed search is a list of answers for all of the questions, each

answer being marked in terms of which question it satisfies. A

subsequent routine sorts these answers into separate lists and translates the arbitrary numbers given in the original output lists into

conventional systematic names for the compounds.

In collaboration with Norma Baird, Opler has also devised a

routine for enabling the 704 to display structural formulas on a cathode

ray tube; when this is desired, some other form of description of the

compound is used as input. ' ' ' A large number of small

structural groups are stored in the machine in a coded form. When an

appropriate description of the compound desired for display is given,

the depiction program calls up the applicable structure codes, converts

each one into a pattern of dots which corresponds to the structural

configuration of that group, assembles the dot patterns in their correct

relative positions, and displays the entire structural formula on the

face of the cathode ray tube. A camera may be coupled with the CRT

to record the displays, or an output magnetic tape may be written

containing the dot pattern words to be used in a later display. Output

rates are about two structures per second for photographic copying, or

five per second for recording on magnetic tape. Opler also found it desirable to modify the output routine of the topological structure

searching routine (described above) so that instead of producing lists

of structure names, the pictorial depiction codes could be brought in,

-26-
converted to dot patterns, and the structure displayed on the

CRT.

In addition to the work described above, Dow Chemical Companyis using a Burroughs 220 electronic computer in its Midland, Michigan,

plant, in a program to develop new rocket fuels, textile fibres,

plastics, and other chemical products.

Midwest Research Institute (MRI) —'

' —'

The Midwest Research Institute is an independent non-profit

research institution, financed largely by gifts from businessmen in the

geographical area of Kansas City and St. Louis. A study is under way

at Midwest (supported initially by a National Science Foundation grant,

the Basic Research Associates program of MRI, and International

Business Machines Corporation) to determine the "structural and

physical attributes which correlate with the uses of chemical

compounds. "

Of approximately 750, 000 different chemical compounds known

at this time, only about 3, 000 have recognized commercial and

medical uses. MRI is attempting to determine applications of the

remainder by the use of high-speed computers.

MRI wrote to manufacturers in the United States and Canada and

through them acquired information concerning commercial products

for their research. They have collected data on more than 2, 000

commercial compounds with known uses and they want to determine the

factors which are keys to those uses. Then, on a statistical basis,

they seek to discover whether other compounds with those factors are

likely to have the same uses. Their routine seeks to determine, then,

not only new uses for compounds for which some uses are known, but

uses in addition for new compounds which have been synthesized but

whose utility has not yet been discovered.

Data for 2, 000 of the compounds have been coded and are

acceptable to the IBM 704 computer in the form of punched cards. MRI

is applying the system to several major categories of chemicals.

-27-
Midwest has a list of "usages" for the compounds; in some

instances there are as many as fifty for an individual compound,

although some have as few as three. Certain physical properties were

known for most of the compounds under study, and they were made a part of the input data. They are: Molecular weight, melting point,

boiling point, refractive index, density, and empirical formula. The

use of two-digit numbers to represent physical property values was

made possible by the following procedure. From Lange's Handbook

2, 000 compounds were chosen randomly as a representative base group;

each of the physical property values for this group of 2, 000 compounds

was ordered and the range was separated into equal groups. A twodigit code number was then assigned for each physical property value,

corresponding to the percentile of the particular constant in the group.

This procedure did not sacrifice accuracy to any required degree.

An example of this code for dimethyl phthalate is shown below:

Property Actual Value Code Percentile

Molecular Weight 194 49

Melting Point 5.5°C 17

Boiling Point 285°C 78

Re fractive Index 1. 516 53

Density 1. 189 43

Empirical Formula* C 10

H 10°4 CC10HH10004

*Where only one letter is required for the element, it is repeated in

order to standardize spacing.

Four different data tapes were used for the IBM 704 computer

routine. One of these (1) contained the coded physical properties data;

one tape (2) contained the coded "use" data, consisting of six-digit

numbers, made up of a three-digit number for the basic function of the

compound and a three-digit number for the type of material on which

the compound functions; another tape (3) carried the name of the

compound, together with an arbitrary identification number; and the

last tape (4) contained the chemical structure and the identification

number. The name tape is useful for post-search identification, and

the other three are working tapes.

-28-
The structural code is that used by Norton and Opler in the Dow

125/ 129/ Chemical Company research, with some modifications. ' ' ' Seven-digit code numbers are assigned to commonly occurring

structural groups and linkages in organic compounds, of which there

are something over 300, but provision is made for expanding the

number if need arises. Of the seven digits making up each number,

three refer to identification of the particular group and the remainder

relate positions of mutual attachment between the subject and the

preceding group.

The Midwest researchers have continued Opler's practice of

"multiplexing"; that is, they handle simultaneously ten sets of search

criteria, each of which consists of a series of six-character words

describing physical constants or uses. A separate IBM card is

punched for each such set of test criteria, with the remaining sixcharacter words on the card supplying data for the structure search.

Each compound is classified first into broad classes, and

subsequently into successive sub-classes, up to a limit of three for

the sub-classes. One such example is:

Solvent (Broad class)

Rubber solvent (Sub -class)

Organic rubber solvent " High-temperature organic rubber solvent "

If there are no usages specified for the compound being searched, that

search is skipped; the same procedure applies to the absence of any

physical constants. The broadest classification that can be used as a

test criterion is the basic function of the compound, with the finer

classifications refining the search to more restrictive classes of

material. Five types of search are possible:

(1) Compounds having usage in a specified class or sub-class,

where four such levels are possible.

(2) Compounds with physical constant value

(a) Specified, or

(b) Within limits

-29-
(3) Compounds having a specified minimum or maximum

number of specified structural groups.

(4) Compounds having a specified minimum number of direct

connections between specified structural groups.

(5) Compounds having a specified minimum number of indirect

connections between specified structural groups.

Compounds are grouped according to use, and once it is deemed

that a sufficient number has been accumulated under a use, statistical

analysis is made of the group. Use categories are incorporated in a

tape together with the encoded properties and characteristics of new

compounds, and the compounds are tried against the use categories.

It is possible to specify as an addition a special output which is

a frequency distribution for any specified physical constant or chemical

element. Both a frequency distribution table and a cumulative frequency

table are obtained as a result, and the tables are printed out, after

which a general or a weighted distance function analysis is made of the

results.

Not only physical properties are distributed, but also the

frequency of occurrence of functional groups, inter-relations of

functional groups, types of atoms in the compounds, etc. , until a great

many correlations have been made. When certain compounds have

physical properties which diverge greatly from the majority in that

use category, the anomalies are investigated in an effort to "unlock

new areas for developmental research. "

The MRI researchers say that "the first function of this program

is to describe the statistically significant requirements for each use in

terms of physical properties and structural characteristics. The second

is to screen old and new compounds for possible uses. " They expect

the screening to indicate the most promising areas for the laboratory

work necessary to confirm the ideas so developed. Not only do they

expect to decrease development costs and discover better chemicals

for many uses, but they expect that a significant result of their research

will discover concealed correlations and "substitute a methodology for

the current confused and varied approach to use development. "

-30-
Monsanto Chemical Company

Monsanto's stated aim was the design of a total mechanized

documentation system, with the completion to be realized in small

increments. An integral part of the system design is the manner of

encoding, storage, and retrieval of chemical structures, including

indexing the structures and their retrieval by classes, when desired.

Monsanto's research at this time is concerned with nearly

30, 000 compounds. Each compound has a unique number assigned to

175/

it. In the early work, ——' four magnetic tape files were maintained,

where each of the classes of information listed below was contained on

a separate magnetic tape, in variable length records:

1. Compound's structure and number

2. Compound's name and number

3. Compound's test results and number

4. Compound's molecular formula and number

174/ Later work ' makes use of the first three listed; the last is

computed and stored with the structure data.

Initially, the coded information describing the structure is

punched on 80 -column IBM cards, together with the unique identification number. A maximum of ten cards may be used for each record.

The program for performing different types of searches is contained

on a deck of cards, and included with it are the necessary control cards

to perform the specific search required. The search was previously

carried out on an IBM 702, but the details of the work are reproducible

with either the 702 or the IBM 705 computer; and the IBM 704 is at

present being used for searching.

There is little redundancy in the system, which Monsanto feels

is a limitation with respect to certain types of error -detecting

procedures. Proof-reading is employed in an effort to catch human

errors. Some such errors are found occasionally by chance by

trained chemist users of the output data. Monsanto does employ

certain known characteristics of the data as safeguards in several

-31-
editing and error checking procedures, e.g. , a test as to the oddness or

evenness of numbers of characters in a row, or of number of rows of

data for a structure, and tests which make use of chemical valence

rules.

For the "application-research"* carried on at Monsanto, a new

method of encoding structures of chemical compounds was developed for

automatic storage and retrieval. The encoding scheme used by

Monsanto is a relatively simple one, and the encoding can be performed

by trained clerks instead of professional chemists. Structures are set

down on cross-hatched paper with numerals used for chemical bonds,

single character letters for the elements, and the letter "M" used for

all metals. The elements and bonds are written in the squares of the

paper in the same arrangement as the original structure written by the

chemist. One example of a structure so encoded is shown as follows:

Encoded data

C1C2C10

2 1 C1C2C

Under the topological principles employed in the philosophy of the

system, the chemical elements can be thought of as hard cores, which

are joined by the different types of chemical bonds, thought of as

flexible links, and the configuration may be twisted into a large number

of shapes. Provision is made for recognition of the compound,

regardless of divergence among chemists in forming and encoding the

structural diagram of the request.

The computer calculates the molecular formula, and the complete

tape record contains: compound number, molecular formula, controls

and structure data. Control data include the molecular formula

requirements and the substructure. A chemist may search the files

for a specific substructure or chemical moiety, instead of the complete

As defined by Monsanto Chemical Company: "that type of work in

which an attempt is made to find a chemical to do a specific job. "

-32-
structure, if he desires. The search strategy may use the molecular

formula as a screen, before continuing further detailed searching.

Monsanto also uses the computer for report writing. A

"screening report" is prepared on each compound tested, and the

running of tests for specific applications requires the distribution to

interested personnel of about 20, 000 different screening reports each

year. Results of the tests are stored in the files in the form of one of

three statements:

1. No further interest

2. Some activity, a lead for further study

3. Active, needs secondary screening or field testing

For the report writing, a standard preprinted form is not used;

rather, for purposes of flexibility and revision, the output format is

pre-programmed and printed out each time by the machine. The

computer searches name and structure for the input compound number,

then prints out on the desired format the information pertinent to the

test being reported. Six copies are made, and are ready to be mailed

at output. The output from the computer is in some cases a twodimensional printed structure which can be recognized by trained

chemists. Monsanto chemists say the computer -printed structures

are easy to read and interpret. The one -page laboratory report output

contains the serial number of the compound being studied, its name,

structure, the raw data recorded, and an evaluation.

For report writing, Monsanto recopies data in various

combinations for progress reports, special reports, process reports,

and others. Requests to regenerate stored data in repetitive situations

are called "bonus questions" by Monsanto, as the cost of each such

successive request is materially lower than the preceding requests for

the same information. In addition, they have found it economical to

accumulate lists of various combinations and cross -combinations of

tests made under varying conditions, and they use the material so generated to form meaningful sets of tables.

-33-
In addition to the screening report, monthly summaries of data

are made up and distributed to interested personnel of Monsanto,

consisting of lists of results according to each of the three test

findings. Special reports may be ohtained, such as review of results

for new synthesis leads, further testing, or collection of data for any

one period.

Monsanto has made several hundred generic structure searches.

They say that the data are ready to be searched for almost any twodimensional structural fragment needed. The machine accepts the

encoded structure, analyses it for searching purposes and updates the

file. Monsanto considers that its work is now definitely out of the

research stage, since it is now an integral part of their reporting

176/ system and information retrieval program. ' Ray and Kirsch Work at NBS.

The U. S. Patent Office and the National Bureau of Standards are

engaged in a joint long-range research program to develop and apply

automatic techniques of information storage and retrieval to the

problems of patent searching.

An experimental program was written for SEAC, the electronic

digital computer at NBS, to make atom-by-atom structure searches

142/

in the field of chemistry. ' Codes were written to describe over

200 steroid compounds; this compilation was used as the search file.

The method of representing chemical structures in diagrammatic

form lends itself to a consistent notational scheme. For the purposes

of this experiment, the compounds were encoded by arbitrarily

numbering serially each atom in a structural diagram. One computer

word was designated to contain the number of the atom, plus the

numbers of other atoms to which it is attached. The number of such

attached atoms was limited to four. In addition, the element symbol

was also included in the SEAC word, which thereupon contained six

fields: the serial number of the atom, the element symbol, and four

connection fields.

-34-
The coding for chloral, for example, is as follows:

CI H

CI C =" 7

CI

CI

5

CI

CI

4

H

3 2 1 C =

The atoms and all bonds (other than single bonds) are numbered

in any arbitrary order. The list of connections to each component of

the structure is as shown below:

Component No. C<Dnnections Element Symbol

1 2

2 1-3 =

3 2-4-6 C

4 3 H

5 6 CI

6 3-7-8-5 C

7 6 CI

8 6 CI

The SEAC search program seeks to make an atom-by-atom

match between the specified question structure and each entry in the

search file. It is possible to request a match of a fragment, and

thereby to find a particular configuration contained within a larger

structure, or to match all components of a complete structure. In this

sense, the generic concept is introduced into the search program.

-35-
Each match made in the search program is considered tentative

until the search of the first file structure is completed. Whenever a

failure to match is discovered by the program, it tries to return to

the previous match to make a new match. If all possible matches

lead to irreconcilable mismatches, the program rejects this file

structure and progresses to the next.

A data checking routine is a part of the program. The original

file, prepared by the Patent Office, was in the form of about 2500

punched cards which described about 250 chemical structures. The data

were checked for internal consistency (including the redundancy feature

inherent in expressing the attachments of one piece to another) and for

their adherence to the coding rules that had been established.

Ray and Kirsch suggest that, to speed up the searching procedure,

the empirical formula be used as a screen, and that only those

structures be examined which have at least the number of occurrences

of atoms required.

HAYSTAQ

One result of the collaboration between the U. S. Patent Office and

the National Bureau of Standards, carried out in accordance with a

I/O / congressional mandate and recommendations by the Bush Committee,

is the electronic computer system known as HAYSTAQ. This program

attempts to simulate the search which a patent examiner now makes

manually; the scope of the search is confined to the area of chemical

literature. ' '

Patent Office searching problems present some peculiar

difficulties, and the need for mechanization of some of their search

procedures is growing more pressing because of the rapidity with

which technology is advancing and technological publications are

increasing. A statutory requirement is that patentability be

predicated on novelty, utility, and inventiveness, and these factors

must be taken into account in the design of any mechanized searching

system.

3 6-
The first computer routine devised for the HAYSTAQ system was

a general searching routine which was written for the NBS computer

SEAC. Patents or other documents are coded and are contained

serially in the file. Each such document is divided into compositions

(physical admixtures of materials), subdivided into items (ingredients)

and further subdivided into descriptor words (see Fig. 1). Heading

information for identification, screening, and housekeeping precedes

the file information contained at each unit level.

The question is stored and remains in SEAC's internal storage

during the duration of the search. Compositions are read in serially

and by a matching procedure on the individual descriptor word level,

an attempt is made to "find" a respondent among the disclosures*

making up the file. Screening techniques are employed at each level of

the search for the purpose of terminating the search as soon as it is

discovered that a match cannot be made. The descriptor words within

the items for both question and disclosure are ordered for the same

purpose, in ascending order of initial digits according to descriptor

types (see Fig. 1). The initial digits refer to the differing subject

categories.

Examples of Descriptor Types

10000004852 - Index number

2043C05E901 - Empirical Formula

3 _ Chemical

4 _ Botanical

5 _ Zoological

6 - Anatomical

7 _ Processes

8 - Miscellaneous

Fig. 1 When a complete match is attained for a composition (on either an

exact match or a "contained-in" basis) a record is made in a so-called

_ A disclosure is any one of the many documents making up the

encoded file which is being searched.

-37-
"hit word" and the search progresses to the next composition in the

document. The total score making up the set of hit words is then

analyzed to determine whether the combinatorial relationships among

the several items are the ones sought and whether a sufficient number

of real answers has been found. This is necessary because one

question item may be answered by several disclosure items, or, more

seriously, one disclosure item may be the only answer for several

question items, where several disclosure items are required. Also,

several disclosure items may be wanted only if they are in combination,

and they may instead be in an alternative relationship. Provision is

made in the search for AND, OR, NOT, and ABSENT relationships.

Provision is made in the search for a combination of five possible

question item types with three possible disclosure types, for a total of

fifteen different combination search paths (see Fig. 2). Determination

is made in advance of the particular question and disclosure type

combination, and the suitable search path applicable to this

combination is chosen. The characteristics of the data are allowed to

determine the choice of the proper subroutine, to the exclusion of all

others; this technique permits direct access to the pertinent orders

without lengthy tests or questions.

Q (question) Item Type D (disclosure) Item Type

All Q descriptors positive All D descriptors positive

Some Q descriptors positive, Some D descriptors positive,

others negative others negative

All Q descriptors negative All D descriptors negative

Some Q descriptors positive,

others absent

All Q descriptors absent

Fig. 2

One of the subroutines included with the general routine is an

examination of the empirical formula to seek a match. Another subroutine involves a matching of chemical descriptors. As test cases

were tried, the importance of the chemical descriptor loomed much

-38-
larger in the overall system, and it was decided to expand this part of

the routine into an independent routine -which could be used separately

when desired. The latest HAYSTAQ routines are concerned with this

expanded subroutine, which is much larger than the parent routine.

The generalized search routine is concerned with a small-scale,

or bird's eye view of documents; the chemical descriptor subroutine

brings up a magnifying glass for an intensive large-scale look at a

smaller section. There are several problems which cannot be dealt

with satisfactorily in the general system for several reasons. For one

reason, it is an exploratory program from which it is hoped to gain

experience as to future directions for exploration; for another,

limitations of available computer capacity made it necessary to limit

the scope of the search. Solutions for two disturbing problems which

have not been adequately provided for in the first program were

included in the chemical descriptor search: one is a method for

handling structural formula "Markush" groups;* the other is provision

for asking a question generically and accepting as a satisfactory answer

any specific embodiment of the genus. In addition, provision is made

for searching for an exact match, or for a fragment which may be

contained within a larger configuration.

A study was made of two other systems which employ recognition

of topological relationships among functional groups: that of Norton and

125/ 129/ Opler at Dow Chemical Company (-* L an(j the Ray and Kirsch

142/ system at NBS. ' The Norton-Opler system with relatively large

functional groups was considered to be too rigid for HAYSTAQ, and the

Ray system was in too fine a detail, embodying as it does an atom-byatom match, and was therefore too slow. Basic functional groups which

make up the particular compound were chosen, and the topological

relationships among them shown, without an indication of positions of

attachment. Terms are also provided which represent combinations

of two or more units of the basic functional groups; these are groups

which have constant definitions and are recognizable by chemists.

A "Markush" group is an art term used in the Patent Office for

designating a synthetic genus by a listing of its members.

-39-
An additional category of terms which are generic in nature (halogen,

ester, etc. ) is also provided. In the stored and coded form of data the

combination terms and the generic terms precede the functional group

terms and they may be used either as screens for the functional group

codes or they may be used as the subject matter of search questions

themselves.

The data are ordered, both in the disclosure and in the question,

in an ascending series, according to the numerical value of the codes

representing the substantive information. Since the program is

essentially a matching procedure, this permits the computer to

determine (in searching for a particular term) at the earliest possible

moment when there is no available answer.

Rings and alkyl groups, because of their frequent occurrence, are

recognized and given special consideration in order to promote greater

efficiency in the program.

The search proceeds in serial fashion through the two summary

categories (combination and generic terms) and the topological - functional group terms. If it is determined that the required

combination terms are present, the search progresses to ascertain

•whether the required generic terms are present, and, if so, whether

they are properly defined in the more detailed data. If the searching

criteria in these two sections are satisfied, the routine progresses

to the topological search in the functional group data.

An "equivalence table" is kept of identifications of matching items

on both the question and disclosure sides. If there are present more

than one of any identity in the topological groupings, there is a

possibility that the wrong such identity will be selected. If that occurs,

when the mismatch is detected the program allows for a backup in

another attempt to find a match and the data are examined to attempt

to find another embodiment in the disclosure data which will satisfy the

question.

In the case of a structural formula of the Markush type (a

structure having a fixed nucleus with variable substituent groups),

if any member of the group on the question side is encountered in the

-40-
disclosure data, it is considered to be a match. This concept allows a concentration of the description of many compounds in a single data

entry; in fact, in one of the test cases which were tried, over

64, 000, 000, 000 distinct embodiments were contained in the one data

listing. This is not astonishing when it is considered that any one data

entry may contain many such Markush groups, and the final number of

compounds which may be represented by the one structural diagram

will represent the product of all possible combinations.

Any failure to match after a backup, when there are no further

entries of the kind sought, will automatically call up the next document

against which to try the question. Any one question is tried serially

against all the data in the file. The program makes extensive use of

screening techniques at all levels of the search. In other words,

information of a general character is examined before proceeding to

more detailed inspection.

Auxiliary data preparation routines are being run against large

amounts of raw data in an effort to accumulate a file which will be used

for testing the efficiency of the system.

Use of the RAMAC-305

Because the IBM 30 5 (a general purpose computer with moderate

speed) has a large random access internal storage, it is well suited

for making searches of the coordinate indexing type. For such use,

the documents to be searched are stored in the memory as an "inverted

file", each record in the storage being based on one of the descriptors

or terms of the vocabulary. At the address where each such record is

stored are listed numbers identifying the documents to which the term

pertains.

At the San Jose Laboratories of IBM, where the earliest work on

48/ 124/

this type of system was performed, Nolan and Firth — ' experimented with 5, 000 documents, most of which were company

reports, articles, and papers ordered by the library at the request of

laboratory personnel. Their dictionary included descriptive terms and

-41-
the address at which the applicable document numbers are stored. This

address was automatically computed by treating the characters of the

ten-letter descriptive words as numbers and:

1. Dividing the word into two five -character portions,

2. Adding them together,

3. Squaring the sum, and

4. Employing the three middle digits of this quantity as the

address of the record.

Since each record (100 alphanumeric characters on the RAMAC discs)

can store only a limited quantity of document numbers, provision is

made for automatically gaining access to "overflow" records. Questions

are asked by punching addresses of pertinent terms on standard 80-

column punched cards and reading them into the RAMAC. The records

stored at these addresses are then compared to find document numbers

which are common to the several records being compared. It is

possible to make searches where the terms are either in the logical

"AND" or the logical "OR" relationships.

In the U.S. Patent Office, Leibowitz et al ' have further

developed a system of this type, which is called DRAM, and which has,

at present, a file of documents on synthetic resins. In addition to the

general features of the scheme used by the IBM workers, the DRAM

system includes provision for additional relationships and for three

levels of increasing specificity of the dictionary terms. Compounds

are searchable as such, or in terms of their atomic groupings.

Relationships between compounds involved in processes may be

searched, as well as the roles, functions or uses of compounds used in

any particular process. Provision is also made for searching in terms

of numerical values of certain physical properties (e.g. , melting points

of reaction products) and reaction conditions (e.g. , pH of reaction

mixtures). Additional systems of similar nature are also being

53/ developed for searching the phosphates and other compounds. —

Grandine and others, of Kennett Computer Consultants,

Inc. —-'

' -—' ' ' (Kennett Square, Pennsylvania), have used the

-42-
IBM 305 in an experimental system based on the VS, system developed

102/

at the Patent Office. ' The VS., work had been geared to ILAS,

which is a special purpose punched card machine specially designed to

handle interfix logic. Grandine's work included an extensive system

for handling interfixes on the computer, somewhat more than 265 interfix fields being required by some documents. Positive and negative

interfixes were employed, as well as "balancers" whose function was

to remove some of the ambiguities resulting from the use of the positive

and negative interfixes.

The Cancer Chemotherapy National Service Center and

Documentation Incorporated are making use of the IBM 305 in

connection with the former group's project dealing with reports of

the screening of compounds for their possible use in treatment of

103/

cancer. '

Report Searching on the Bendix G-15D at du Pont

Since January 1959, the Patent Division of the du Pont Textile

Fibers Department has been searching research reports by means of

the Bendix G-15D. —' Upwards of 13,000 reports (mainly chemical

laboratory studies) with more than 125, 000 index entries are in the file,

and the rate of accretion to the file is estimated at 15 to 20 per cent per

year. Names of compounds, uses, physical properties, and other data

are recorded on magnetic tape. Each such indexing term is assigned

a four -digit alphanumeric code; all of the codes for a document,

together with identifying indicia, are recorded as a variable length

block on magnetic tape. The searching program, which is stored. on

the drum of the computer, causes comparisons to be made between all

question codes and all file codes. However, to speed up the operation,

the codes for each document have been sorted numerically. The lowest

number is stored, and subsequent differences between adjacent codes

are stored, rather than the complete number in the succeeding

instances. This permits a more rapid searching operation, since less

than the theoretically required number of computer orders must be

executed. The questions are read in from a punched paper tape. Each

question code can be asked for positively or negatively; in the latter

-43-
mode, documents which contain negative codes are excluded. Relationships among the codes for a document are not recorded. Answers for up

to 16 separate questions may be searched for simultaneously, provided

that not more than 16 discrete codes are included. The workers report

that "the chief cost and time-consuming bottleneck is the manual

screening of answers to eliminate semantic noise from the results of

the machine search. "

Thermophysical Properties Research Center (Purdue University)

The Thermophysical Properties Research Center (TPRC) at

Purdue University collects all available recorded information on the

thermophysical properties of all substances, including the theoretical

methods of determining the properties and the experimental techniques

166/ used in measurement. ' One of the principal sources of the material

is from the abstracting journals, which cover approximately 15, 000

technical and scientific journals. Since the cost of searching the

journals by highly trained scientific and technical personnel at TPRC is

extremely high, an alternate search procedure has been developed

there. Searchers locate and mark pertinent references; clerical

assistants label them and assign code numbers to thirteen specific items

of information selected to identify and describe the contents of the item.

The thirteen coded items are contained in the first forty columns of

standard IBM cards, and one or more cards are required for the code

of each abstract; additional cards are used for more than one property

or substance, or for more than one physical state for the material under

study. The thirteen items contained on the card are as follows:

Property, substance class, substance name, physical state, type of

subject coverage, language of original article, serial number of the

reference, journal name, journal volume, journal number, journal

series, beginning page number, and journal year.

In addition to the codes listed above, a further breakdown is

required for substance classification, as follows:

-44-
Series -000: Works not involving substance class

Series -100 and -200: Substances described by chemical formula

Series -100: Elements and compounds (except

compounds containing both C and H)

Series -200: Compounds containing both C and H

Series -300: Ferrous metal alloys

Series -400: Non-ferrous metal alloys

Series -500 and -600: Substances which cannot be described

correctly by a single chemical formula and

are not metal alloys

Series -500: Chemical systems and combinations

Series -600: Commercial and natural products

TPRC uses a Datatron electronic computer, with two magnetic

tape units and an Electrodata 500 Card Converter. The data cards

containing the thirteen selected items of information concerning the

document are sorted by property, by class within property, and by

substance within class, and the information pertaining to each property

is stored on a separate tape. Because more than one journal may refer

to any given article or report, each new potential entry into the file is

held until the file has been searched for duplicates; if the new entry is

a duplicate, it is rejected.

TPRC states that the separate magnetic tape for each thermophysical property permits rapid retrieval for specific inquiries.

Search queries must specify the name of the substance and the property

desired for that substance. Once each year TPRC issues in book form

an ordered reproduction of all information contained in its files:

"Search and Retrieval Guide to Thermophysical Properties Information. ' The publication, which is issued to sponsors and others interested in

having readily available the information which it contains, consists of

three parts, and has an annual content of about 20, 000 bibliographic

items. Parts A and B, "Guide to Substance Classification and Code

Designations" and "Classified Search Index, " respectively, are reissued every year, with information added to that accumulated for

previous years. Part C, "Master Bibliography and Author Index, " is a permanent volume to which a new volume is added each year.

-45-
Fine Chemical Service (England)

A Pegasus computer, with magnetic tapes, has been used to

search a collection of 25, 000 organic chemicals, together with a file

33/ of relevant physical, chemical, and biological properties. —' Certain

structural features are stored in order to facilitate the selection of

compounds with those features from the file.* The first 208 prime

numbers were allocated to 208 of the structural features; then for anychemical compound, the primes corresponding to its structural

features are selected and multiplied, and the number so obtained is

used as the code for that chemical compound. To find a compound

responding to a particular set of such structural features, the product

(compound number) is divided by the required factors of the combination

desired; a test for a zero remainder will indicate the presence or

absence of any such factor. This procedure will select all compounds

which have at least the given set of features. A similar system has

96/ been employed by IBM, —' and by at least one chemical company in this

country, one of whose representatives said informally that they had

abandoned the scheme because they were "defeated by the division time. "

Farbwerke Hoechst AG

The Farbwerke Hoechst AG (Frankfurt am Main/Hoechst) has

developed a system for encoding chemical structures which enables

searching for compounds and reactions on an IBM 705. The developers

of this system (Fugmann, Braun, Schwalbach and Vaupel) state that they

can handle structures containing variable components, searches

containing excluding limitations, and searches which are generic in

nature.

Reactions are described by coding the affected chemical groups as

they exist both before and after the reaction has occurred. Auxiliary

agents are coded by their elementary symbols according to the periodic

system. Further, numerical terms are used to express the change in

the degree of hetero -orientation of the carbon atoms concerned with the

reaction.

Examples of such structural features are ring systems, amines,

chlorides, etc.

-46-
Coding terms of varying degrees of specificity are provided for

more or less conventional structural groups as well as for such

"quantitative characteristics" as chain length, position of ring

substituents and relative positions of characteristic groups in chains.

From the information available at the time of writing, it appears that

the search involves a coordination of terms in the question and file,

the mere presence of the requested terms in the code for the file

compound constituting a successful search.

In a private communication, it was stated (Sept. 1959) that the

tape file includes more than 20, 000 compounds, that it will increase

55/

to nearly 100, 000 within the year, —' and that the system has been in

use for over a year.

Badische Anilin und Soda Fabrik AG

Dr. Ernst Meyer of the Badische Anilin und Soda Fabrik

AG (BASF, Ludwigshafen) has been developing a topological system of

searching for compound structures employing a general purpose

115/ computer. ' The "cells" chosen to represent the nodes of the

structural network are the atoms. They are represented by arbitrary

numbers, and arbitrary numbers are again chosen for the neighboring

atoms. Identification of the element by a unique symbol (periodic

table) is also recorded. One of the objectives of this project is to place

as much as possible of the burden of preparing the encoded file on the

machine, rather than on humans. To this end, advantage is taken of

the fact that compounds with complicated structures usually contain

large structural groupings which repeatedly occur in chemistry.

Examples of such groups are anthraquinone and benzoylamino. Special

symbols are recorded manually for these groups and the machine

"computes" the atom by atom code. In one example, a structure was

manually encoded in 8 lines, by this method, and the machine was used

to work out the details, which resulted in 100 lines, The savings in

time and reduction in errors are considerable over the same 100 lines

done entirely by hand. The system provides for the handling of the socalled "Markush Structures, " which include variable substituents on

specified positions of a nucleus. Searching may be either for entire

-47-
specific compounds or for compounds which include a given structure as

a fragment. The general pattern of searching through the question and

file structure in a comparison for similarities is very much like the

schemes applied in the HAYSTAQ structural search routine and that of

Ray and Kirsch.

Gmelin Institute

The Gmelin Institute has as its general objectives the

presentation and evaluation in a detailed and critical manner of all of the

world's knowledge on inorganic and physical chemistry and related

sciences. The ever increasing volume of the literature has compelled

the Institute to study mechanical methods of classifying and filing

abstracts. While as yet mechanized information storage and retrieval

systems are not in use at the Institute, a research group headed by

K. Schneider has produced several experimental systems. One

tnc

149/

searches documents on atomic energy on the IBM 650; another

searches similar subject matter on the Univac Fac -Tronic I;

' and

a third, also for use with the Fac -Tronic, has as its subject matter non4 ii 150/ ferrous alloys. '

Lj-

-48-
DIFFICULTIES, LINGUISTIC AND OTHER

Almost every literature searching project now in development is

encumbered with some, at this time, unre solvable difficulties. Studies

are under way by several groups engaged in special efforts on

resolution of difficulties, which represent in some cases segments of

the main problem. One primary difficulty embraces the entire area of

linguistic considerations. Language in the form of discrete words is

the usual means of communication in printed or written material.

Language in this form is not understood yet by computers without an

intermediary of some kind. A synthetic solution of the difficulty of

communication between humans and computers is that of creating an

intermediate language of symbols, where a unique symbol expresses a

word or an idea, and the computer is programmed to substitute the

symbol for the idea, or "thing", so expressed, and to recognize the

concept or the object by means of the symbol expressing it. This sort

of procedure, however, is practicable only in files of limited subject

matter and size.

For several years, S. M. Newman, at the U.S. Patent Office, has

been concerned with the creation of an unambiguous special language

for the expression of ideas and objects, and their relation to each other;

123/ he calls this language "Ruly English". '

E. de Grolier has proposed the creation of a general machine

language, which would also be a link to join different translating

38 7 machines working with natural languages. -1— He points out, however,

that many scientific disciplines must be brought together for this work,

including classification, linguistics, and logic. Among others who are

working in this area are Ranganathan in India, Vickery and Foskett in

England, Scheele in Germany, Durocq in France, and several

Americans whose works are cited elsewhere in this report.

V. Yngve, at MIT, advises the use of an automatic programming

system as an intermediary between the linguist and the computer,

where the linguist employs in his research a notation or language called

"COMIT"; that language in turn is converted by a conversion routine or

-49-
compiler. Through such a language, Yngve states that the linguist can

direct the computer to analyze, synthesize, or translate sentences. He

advocates the use of English text in literature searching because of the

possibility of missing a reference when indexes or abstracts are used,

in spite of the complexity which this procedure introduces into the

searching. A group at Lockheed is studying word correlation with

respect to the syntax of English; "a normalized English language is

formulated in terms of which all other words are syntactically defined",

after which correlation factors are computed by counting primitive

117/ words occurring in syntactic reduction strings. ' Another group, at

Ramo-Wooldridge, has been conducting research on word correlation

and automatic indexing for information retrieval procedures (under the

sponsorship of the Council on Library Resources). '

Thyllis Williams, at Itek Corp. , advocates applying to natural

language a "normalized representation" for the storage of index data;

she calls this "L-representation" and employs an "L-dictionary" of

special rules for correlating elements of non -normalized expressions.

An L-thesaurus is also employed for the purpose of relating the

normalized representations to stored index data. She maintains that

the informative content of a document is usually represented

incompletely in indexing it, and that under the system of L-indexing,

it can be developed to a greater depth and specificity for a searching

. . ,•'•,,. 84/, 100/, 191/ system employing selective indexing. —

75/ Both Harris, at the University of Pennsylvania, —' and Chomsky,

30/

at MIT, —' have been engaged in linguistic research which may be

applicable both to machine translation and to literature searching.

Harris's work has resulted in computer programs for the UNIVAC, and

some of his followers have applied his ideas on other computers.

However, there has not as yet been a significant "breakthrough" to the

extent that there exists a tool which can be employed productively for

making literature searches independent of an intermediate symbolism.

Bar-Hillel has written a critical review of work done in this and

12/

related areas of mechanization of information searching problems. —

-50-
In the linguistic problem, there are two primary aspects:

semantics and syntax. Some researchers have approached their study

initially through semantics, some through syntax; some have used an

empirical approach which incorporates both aspects. Much more work

is needed on both. Any approach to the study of language solely

through semantics is a dangerous one. Among the problems

encountered are semantic changes which take place with the passage

of time; there are additional complications in the changing conditions

in science, such as, e.g. , changes in the use of physical constants,

changes in the accepted values of precision in measurement, or even

in the standards of measurement employed.

A great deal of current research is being conducted on character

recognition devices, which should assist eventually in the reading of

English (or foreign) language text by computers. A certain amount of

development in this field has made available some commercial machines

162 /

for this kind of activity. '

Difficulty of developing a system for literature searching varies,

of course, from project to project, and depends partially upon the

objective of the search, the magnitude of the file or library which must

be searched, and the fineness of discrimination which must be built into

the search program. The scale of the search might run from a simple

hunt for a matching name or title to an all -encompassing search

similar to those required by the U.S. Patent Office.

While it is likely that one could develop a mathematical model of

any existing retrieval system, no one has yet set forth a comprehensive

model which might be generally applicable. The value of such a model

would lie in the ability to predict the characteristics of systems under

development; to correlate properties of existing systems so as to permit

comparative studies to be made, and, hopefully, to serve as a guide to

the establishment of really useful and economical comprehensive search

systems. A number of research workers have concerned themselves

with developing general theories in this field and the recent International

Conference on Scientific Information devoted an entire session to this

problem. —' ' '

-51-
An enormous difficulty to be surmounted in designing any system

for literature searching is that of preparation of the file to be searched.

Every stage of the journey from natural language and figures,

illustrations and diagrams (the form in which it is assumed most

literature would be found initially), through the analysis by professional

personnel to extract pertinent material (or to abstract or to transfer

material entoto), to the final form of the information on some magnetic

medium, is studded with formidable obstacles. Thyllis Williams's

concern regarding the preservation of the informative content of a

document is a very real one. Although the analyst of a particular

document may extract all information which is pertinent to requirements

envisaged for any particular system, or for others in the foreseeable

future, some information content is lost when a complete document is

not retained, and the value of the missing material may depend upon

inventions not yet in existence and whose development cannot

45/ reasonably be anticipated. —' It is extremely important, but extremely

difficult at this stage of development, to insure that there will be

adequacy of analysis of documents, and proper coverage of all material

contained in them. It is perhaps for these very reasons that Yngve

insists so strongly on preservation of the natural language input as one

prerequisite for proper subsequent retrieval.

The accuracy of any data which have been handled by humans at

any point is suspect; on the other hand, machines which handle data

cannot use "human judgment", and it is difficult, if not impossible, to

formulate rules for processing every situation when diverse kinds of

data are handled by machines. There simply does not exist any foolproof method at this time for transferring hard copy information

directly to a magnetic medium with any assurance of obtaining an errorfree file.

The basic approach to the design of a system for information

retrieval varies widely. For some retrieval problems, a set of

descriptive terms called "descriptors" is stored for each entry in the

file. Some retrieval attempts require the specification of identical

descriptors in order to recover the stored information. A broad or

-52-
general specification might deluge the questioner with answers if

(a) the file is extremely large or (b) the question is not asked in

sufficient detail to screen out all of the unwanted items having duplicate

descriptors. One criticism of this kind of file is its unwieldiness

because of size; another is the difficulty of phrasing questions in order

to avoid large numbers of "false drops. " One fashion of forming a file

for such a system is by means of an "inverted file" structure, where,

instead of listing under a document the descriptors applying to it, the

file categories are made up of characteristics of material in the

documents, and under each such descriptive heading is a list of the

documents which contain material of such a category.

A more succinct file can be obtained by the use of precise

definitions for wanted information from the file, but this procedure is

not possible in very many applications. A chemical structure lends

itself to representation in this fashion very readily, since it permits

exact definition in terms of molecular (empirical) formula and topological arrangement. Where an exact definition can be specified, any

question which is formed for the purpose of retrieval must be equally

exact if only pertinent responses are to be elicited.

Sometimes arrangement of the files in terms of the most

frequently desired items is preferable, particularly if a serial

procedure of searching is employed. The greatest activity is then

concentrated in the area where the information most often required is

clustered, and a more efficient operation results. Most searches,

regardless of the manner of arrangement of material in the files, are

serial in nature, according to the plan for retrieval. An ideal system

would permit an inquiry to be made of the complete file simultaneously,

with a simultaneous response from every entry which is being called for;

at this time neither equipment nor systems for retrieval have reached

this stage of development. An approach to it, however, is in the

concept of selective use of random-access storage in terms of

addressability, where symbols for information coincide with the address

where the information is stored, so that instead of serial searching,

selective searching is employed. Sir Robert Watson-Watt has stated:

-53-
"When he asks for a random-access memory, the client usually wants to

have whatever may be the converse of a serial-access memory.

Physically the answer has reduced to a very rapid-access (and still,

most frequently, a serial-access) device, but philosophically, in the

end it need not, and practically it should not, do so. " He suggests that

the operation which is usually desired is a "Parallel partial -identifier

search" and he further points out that what is wanted is "assured timely

individual retrieval by selection, preferably by parallel interrogation of

the system's 'memory'". ' Sir Robert referred to a paper by Slade

and McMahon which holds promise of providing the kind of parallel

rapid-access storage which is needed for literature searching:

"(1) capacity for storage of a large number of fixed-length words,

(2) parallel interrogation with simultaneous access to the whole memory

and (3) many interrogate operations and relatively few erase and write

operations. "

Until the development of such storage has been completed,

however, a simulated parallel storage can be partially realized by more

sophisticated system designs which permit interrogation of only likely

respondents by selective addressing or summary screening techniques.

Semarne has applied symbolic logic to screening techniques. ' ' '

Vleduts has specified as a necessity "large long-time high-speed

machine memories. . . . . capable of long-time storage or large volumes

of information and of operating without mechanical motion, by using

purely electric counting principles. " Such a machine is said to have

been developed in Russia by Prof. L. I. Gutenmakher, at the Electric

173/ Simulation Laboratory, U. S. S. R. Academy of Sciences.

A large amount of effort has gone into automatic indexing and

abstracting of English language text, because of the sheer magnitude of

this task. P. B.Baxendale has said that the "abstracting and indexing

of input documents represents at least 80 per cent of the effort of

current literature -searching systems as against 20 per cent devoted

13/

to retrieval. " —' In an effort to force computers to assist in this

one-sided effort, H. P. Luhn, together with a group associated with him

-54-
at IBM, has for several years been concerned with "auto -abstracting"

of documents by computers, where the abstracted portion is based upon

a statistical analysis of the frequency of occurrence of words, in

76/, 85/, 111/, 146/ mv . , , . , context . —' —'

' ' The abstracts are made up of whole

sentences from the text of the document, where the sentences are

chosen not only with respect to the presence of certain words, but also

with respect to the relationship of those words to each other in terms

of their location in the sentence. Word lists are formed, excluding

articles, prepositions, conjunctions, etc. , and the most frequently

used words are assumed to be of "high significance. " From the number

of these words in a sentence, and how closely they are clustered among

the other words in the sentence, a "sentence significance factor" is

computed. Those sentences with high scores based on these factors

are extracted from the document to form an Auto -Abstract.

Some information retrieval systems have adroit indexing schemes

for relating discrete portions of files when a unified response is

desired. In this way, segments or fragments may be recovered in the

context in which they are physically located, or they may be tied

together in diverse ways for several levels of maneuvers. Complexity

of such arrangements of course requires more intricate designs for the

manipulation of data so arranged.

Vleduts discusses the application of modern mathematical

statistics to chemical information (as well as to experimental physics)

as a means to a more compact representation of the information

contained in the tremendous archives which have accumulated in

research institutions, but he states that it is effective only when

statistical methods are used not only for the final processing, but in

the planning stages as well (arrangement of material, choice of number

173/ of parallel measurements, etc.).

Another form of disposition of files is that proposed by Newell,

155/ Simon and Shaw, ' where data making up an entity are not

necessarily arranged together in contiguous storage locations; instead,

-55-
the data form a "trail" where each datum carries the association with

what precedes it and what succeeds it. * This particular arrangement

allows facility of amplification of data entries without massive

rearrangements of data in storage. It also permits new entries or

inserts, without dislocating former entries. In the same manner, it facilitates deletions of unwanted or no longer pertinent information.

The unwanted locations are simply returned to storage for later use by

successive entries. Unfortunately, with present equipment, this type

of arrangement demands a certain amount of interpretive programming

and requires a very large random access storage. Information

processing language (IPL) VI was employed to describe the operations

defined in the paper cited above; the authors are now engaged in

developing IPL VII, which is expected to be able to handle more complex

situations.

Most of the chemical literature search systems discussed in this

paper do not take advantage of some of the advanced techniques with

respect to data arrangement and format. The logical problems of

setting up such a system for computers are formidable enough, without

the application of several levels of sophistication in programming

techniques and data arrangement. In addition, the incorporation of such

intellectual advancements to programs now in existence is probably not

worthwhile until a plateau of development in literature searching is

reached, because of their high cost in both time and money. Some of

the improvements which could be put into programs now in existence

might well he abandoned before they have proved themselves because of

advances in the state of the art.

One of the important features to build into future searching

programs, once there has been a changeover from research to

development, is the incorporation of some sort of learning technique in

order to avoid multitudinous repetitive searches. This is a very

important consideration which should be kept in mind, although its

advent will be in a later phase, after the initiation of continuing

See also 97/, p. 1163, 1164.

-56-
programs. A program making use of selective storage recall

operations and employing certain elementary learning methods, called

IQ, has been written by M. E. Stevens, of the National Bureau of

Standards. It is of interest to note that this program has been used

experimentally in conjunction with an output routine for an information

retrieval system. !£!/

Although rapid advances continue to be made in the speed with

which arithmetic calculations can be performed, computer manufacturers have been slow to incorporate into computers special

devices which would aid materially in making searches. At least one

computer manufacturer now is incorporating "search units" into a

77/ general purpose computer. —' The inclusion of such equipment in

computer design (perhaps as an optional feature) could well become a

trend, and would not only cut down the search time by a very large

amount, but would make unnecessary some of the refinements in

programming techniques, which are costly, but will become

increasingly necessary in the absence of special hardware

characteristics.

Certainly one of the difficulties encountered in all literature

searching programs is the lack of appropriate automata with which to

conduct the searches. Computers were originally designed to compute;

there has been a lag in satisfying the need for automation in other

areas where the need is just as great as for computers. Extremely

large random-access storage with rapid "symbol manipulators" are

, 69/, 112/, 122/, 135/, 160 A 178/ _. ., , required. —^ '- '• ' ' ' Since those who are

designing systems for literature searching do not in general have

available the kind of automata which specifically meets their

requirements, they must simulate such equipment by the use of

computers. It is presumed that even this difficulty will be surmounted

in the not too distant future, particularly since so much interest has

been awakened in information retrieval in the last few years.

-57-
CONCLUDING STATEMENT

There is a distinct possibility that the authors may have missed

important work which should have been recognized in this survey. If

that is the case, reports of such work, either complete, or in progress,

are hereby invited. There has been no intentional omission of any work

in the area delineated at the beginning of this survey.

Two invaluable series of reports issued by the National Science

Foundation should be mentioned. One of these, "Current Research and

Development in Scientific Documentation, " which is issued semiannually, contains considerable information on active research projects

in information retrieval and closely related fields. The other, "NonConventional Technical Information Systems in Current Use", reports

from time to time on searching systems in actual use.

In addition to the many fine bibliographies and works otherwise

er of

19/, 78/,

24/ cited in this report (see particularly Casey, et al —' ), a number of

other bibliographies are pertinent to subjects discussed above.

11/' 104/, 105/, 153/, 185/

It is desired to give credit for assistance in the preparation of

this survey to Robert T. Moore, Forest Miller,* and Frances Neeland,

of the National Bureau of Standards.

Now with Union Carbide Corp. , Oak Ridge, Tenn.

-58-
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of

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by

Ethel Marden and Herbert R. Koller*

National Bureau of Standards

Data Processing Systems Division

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•60-
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63
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65
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USC0MM —DC

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U.S. DEPARTMENT OF COMMERCE

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