1P003
7-Azaindole(CH3OH)1,2!"#$%&'()*+,-./01234!56789:;<= = = = >?@= ABCDEFBGH= I!"#$%&'()*+,-./01)23/0456789:;<=>?@A./0BCDEFG
H$%&'IJKLMNOPQRSTUK)VW1<9XYZ[\]9J^I$%&'_`ZaGC
Pb8Scde+fghijklTm>H)nloPpqIrst>cuI()$%&'9vwB78xNP/0yz{<s|t>n}H,-}.>?~A(nl<5IU>7-Azaindole(7AI)(CH3OH)1,2CDEFG9/04$%&'I STPTc?nl<9o)7AI(CH3OH)1,2H$%&'NOPQRt>n})23CDEFG1IQRklc/04$%&'H6mIP2S'^&)/04$%&'HIvkl>n}PSTc? :I)/04$%&'HQRkl>})$%&'ISTm>OH23NH

]¡f9y`¢£¤ZH¥¦kl>?/04$%&'9vw}y`¢£¤Z9§k}94I()¨m5H=>n}H©olTm>9<)OH23NH

]¡f9y`¢£¤ZPªl«l¬I¥¦<l­)C

DEFG1IQRklc/04$%&'9vwIt>®iH¯°o±ol>n}I.>?S
S.Ho)CDEFG1I²f9/04$%&'H³´t>µ')$%&'It>OH23NH
]H²¶I·`X¸[¹t>cu)¯°o±olcy`¢£¤Z9º}/04$%&'9vw94I()»¼. ½¾½ 9¿eHRKc.mµ'Hgm?ªn<À<(),$%ÁÂPc
7AI(CH3OH)1-d1)23 7AI(CH3OH)1-d2Ãdn(,$%ÁÂÄ0fÅ9ÆÇEÈCZ{P¦MS)NHÉ23OHÉ9Ê´ ]P¥¦t>n}IJT)NH23OHÊ´ ]9y`¢£¤Z9º}/04$%&'9vw95PËÌSc?c$%&'PNRt>(a) d03384(b) d1 ND

3367/045678}ST()ÍÎ5678BÎÏ\]5678.Ð
HÑÒol>H)ÓÔ(ÎÏ\]5678I S)Natural Bond
Orbital (NBO)sÕP8mTsÕP.c?

33 219cm-1 exc.

7AI(CH3OH)1-d2;mT)CDEFG9S1!S09 0-0 ß\PXY
GàScIR-dipEÈCZ{P¥¦Sc?c)á0âãä(MP2/6-31++G**/6-31G*)P8mT)CDEFG9NO*å}Æ
ÇEÈCZ{9ãäPc?koI)CDEFG9*LMN

3378

Intensity!Ö×#ØÙÚÛÜ`ZÝÞklc 7AI(CH3OH)1-d1 23

OH str.
(c) d1 OD
33 215cm-1 exc.

OI;mT)NBOsÕ( B3LYP/6-31++G**/6-31G*)Pc?

3372
3391

3382
NH str.

!&}æç#è ½ I 7AI(CH3OH)1-d0)7AI(CH3OH)1-d19IR-dip
EÈCZ{)23 7AI(CH3OH)1-d19réEÈCZ{Pêt?è

3000

3200
3400
Wavenumber/ cm-1

3600

1(a)<()3384cm-1Ivmë[¢H¥¦klTm>H)nl(NHè 1î$%&'NOPQRt>

É}OHÉ9ì¿í ]<=>?½¾½ CDEFGI,$%P

7AI(CH3OH)1 9IR-dipEÈCZ{}r½ Ä0ïðt>n}IJT)UV ñò¡f9ó.> 2 ôõ9éEÈCZ{

IR-dip EÈCZ{H¥¦klc?¯¦9EÈCZ{}réE

23172
3115

ÈCZ{Pö÷Sc&)è 1(b)HNDÉPøt>CDEFG

13288(a) d09EÈCZ{<=K)è 1(c)HODÉPøt>CDEFG9E
3282 (b) d2 ND/OD(1)ÈCZ{<=>n}H/c?c)NH23OHÊ´
-132430cm-1 exc.

-1]Hªl«l)3372cm } 3367cm I¥¦klc?nloP 7AI
3283
OH(2) str.

Intensity

9NH ]¡f)23CH3OH9OH ]¡f}ö÷t>})NHÉ( 149cm-1)OHÉ( 315cm-1y`¢£¤ZSTm>n}H|oI.c?

3178

32414cm-1 exc.
3163

 è 2 I)7AI(CH3OH)2-d0)7AI(CH3OH)2-d29IR-dipEÈCOH(1) str.

Z{)23 7AI(CH3OH)2-d29réEÈCZ{Pêt?è 2(a)<(d) d2 OD(1)/OD(2)3169(vmë[¢H 3 À¥¦klcH)nlo(NHÉ} 2 ;9OH

32407cm-1 exc.

É9·`X¸[¹ùG¢=>?1:2 CDEFGI,$%P 2 Ä31660ïðt>n}IJT)UVñò¡f9ó.> 3 ôõ9IR-dip

NH str.

EÈCZ{H¥¦klc?¯¦9EÈCZ{}réEÈCZ{3000320034003600
Wavenumber/ cm-1
è 2 î$%&'NOPQRt>è 2î$%&'NOPQRt>
7AI(CH3OH)2 9 IR-dip EÈCZ{}r7AI(CH3OH)2 9IR-dipEÈCZ{}réEÈCZ{?
éEÈCZ{Pö÷Sc&)è 2(b)HNDÉ}OD(1)ÉPøt>EÈCZ{<=K)è 2(c)HNDÉ}OD(2)ÉPøt>EÈCZ{)è 2(d)H 2 ;9ODÉPøt>EÈCZ{<=>n}H/c?c)NH É)OH(1)É)23 OH(2)É9Ê´ ]¡f(ªl«l)3169cm-1)3178cm-1)3282cm-1I¥¦klc?nloPùúûG9NH23OH(c) d2 ND/OD(2)

30

1:2
OH(1)

]¡f}ö÷Sc&)25

NHÉ( 352cm-1)OH(1)É( 504cm-1)OH(2)É( 400cm-1yè 3 I)7AI(CH3OH)1-d1)23 7AI(CH3OH)2-d29NHÉ}OHÉ9&'üý}ùúûG9NHÉ}OHÉ9&'üý"r [!10-36]`¢£¤ZSTm>n}H|oI.c?

2010£¤ZºPXY`ZSc&Pêt?è 3 o)y`¢£¤ÃE!]"_{#G-300-400
Red shift /cm-1-200

è 3î5r-500-600

vs Red shift XY`Zi-j*ÅP$uc?NBOù%{<()$%&'PXYZ[&'É9()øÎ0¿*+o)XYZ[,É9d&'*+.9ÎÏ\]IJ>LM}ST/0TUK)E(2)i-j* ($%&'IU>ÎÏ\]567891PdÿSTm>?
n n < ) NBO s Õ < $ u c 7AI(CH3OH)1-d1 U J 37AI(CH3OH)2-d29$%&'9E(2)i-j*I¿ST)Ê´]¡f9y`¢£¤ZºPXY`ZSc&Pè 4 Iêt?

30

1:2OH(1)2520

1:1OH1510è 4 o)ÎÏ\]5678923}y`¢£¤Z923}
94I¨m5H=>n}H/>?JT)7AI(CH3OH)1,2

5-100

1:1
NH-200<()/04$%&'9vwH23t>I4T)ÎÏ\](2)

567891H§h.>n}H|o}.c?

1:2
OH(2)

1:2
NH

E(2)i-j* [kcal/mol]

(2)

1:1
NH

5-100

Z9ºH$%&'9vwPdÿSTm>n}H/>?ko

1:2
OH(2)

1:1
OH15}9þÃ"rîãäºÅI¿ST)Ê´ ]¡f9y`¢I)NBOsÕP8mT$%&'9 2

1:2
NHè 4îE

-300-400
Red shift /cm-1-500

i-j* vs Red shiftXY`Z-600