Bond length - wikipedia Bond length In molecular geometry, bond length or bond distance is the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of the molecule. Contents 1 Explanation 2 Bond lengths of carbon with other elements 3 Bond lengths in organic compounds 4 References 5 External links Explanation Bond length is related to bond order : when more electrons participate in bond formation the bond is shorter. Bond length is also inversely related to bond strength and the bond dissociation energy : all other factors being equal, a stronger bond will be shorter. In a bond between two identical atoms, half the bond distance is equal to the covalent radius. Bond lengths are measured in the solid phase by means of X-ray diffraction, or approximated in the gas phase by microwave spectroscopy. A bond between a given pair of atoms may vary between different molecules. For example, the carbon to hydrogen bonds in methane are different from those in methyl chloride. It is however possible to make generalizations when the general structure is the same. Bond lengths of carbon with other elements A table with experimental single bonds for carbon to other elements is given below. Bond lengths are given in picometers. By approximation the bond distance between two different atoms is the sum of the individual covalent radii ( these are given in the chemical element articles for each element ). As a general trend, bond distances decrease across the row in the periodic table and increase down a group. This trend is identical to that of the atomic radius. Bond distance of carbon to other elements Bonded element Bond length ( pm ) Group 106 -- 112 group 1 Be 193 group 2 Mg 207 group 2 156 group 13 Al 224 group 13 In 216 group 13 120 -- 154 group 14 Si 186 group 14 Sn 214 group 14 Pb 229 group 14 147 -- 210 group 15 187 group 15 As 198 group 15 Sb 220 group 15 Bi 230 group 15 143 -- 215 group 16 181 -- 255 group 16 Cr 192 group 6 Se 198 -- 271 group 16 Te 205 group 16 Mo 208 group 6 206 group 6 134 group 17 Cl 176 group 17 Br 193 group 17 213 group 17 Bond lengths in organic compounds The bond length between two atoms in a molecule depends not only on the atoms but also on such factors as the orbital hybridization and the electronic and steric nature of the substituents. The carbon -- carbon ( C -- C ) bond length in diamond is 154 pm, which is also the largest bond length that exists for ordinary carbon covalent bonds. Since one atomic unit of length ( i.e., a Bohr radius ) is 52.9177 pm, the C -- C bond length is 2.91 atomic units, or approximately three Bohr radii long. Unusually long bond lengths do exist. In one compound, tricyclobutabenzene, a bond length of 160 pm is reported. The current record holder is another cyclobutabenzene with length 174 pm based on X-ray crystallography. In this type of compound the cyclobutane ring would force 90 ° angles on the carbon atoms connected to the benzene ring where they ordinarily have angles of 120 °. The existence of a very long C -- C bond length of up to 290 pm is claimed in a dimer of two tetracyanoethylene dianions, although this concerns a 2 - electron - 4 - center bond. This type of bonding has also been observed in neutral phenalenyl dimers. The bond lengths of these so - called `` pancake bonds '' are up to 305 pm. Shorter than average C -- C bond distances are also possible : alkenes and alkynes have bond lengths of respectively 133 and 120 pm due to increased s - character of the sigma bond. In benzene all bonds have the same length : 139 pm. Carbon -- carbon single bonds increased s - character is also notable in the central bond of diacetylene ( 137 pm ) and that of a certain tetrahedrane dimer ( 144 pm ). In propionitrile the cyano group withdraws electrons, also resulting in a reduced bond length ( 144 pm ). Squeezing a C -- C bond is also possible by application of strain. An unusual organic compound exists called In - methylcyclophane with a very short bond distance of 147 pm for the methyl group being squeezed between a triptycene and a phenyl group. In an in silico experiment a bond distance of 136 pm was estimated for neopentane locked up in fullerene. The smallest theoretical C -- C single bond obtained in this study is 131 pm for a hypothetical tetrahedrane derivative. The same study also estimated that stretching or squeezing the C -- C bond in an ethane molecule by 5 pm required 2.8 or 3.5 kJ / mol, respectively. Stretching or squeezing the same bond by 15 pm required an estimated 21.9 or 37.7 kJ / mol. Bond lengths in organic compounds C -- H Length ( pm ) C -- C Length ( pm ) Multiple - bonds Length ( pm ) sp -- H 110 sp -- sp 154 Benzene 140 sp -- H 109 sp -- sp 150 Alkene 134 sp -- H 108 sp -- sp 147 Alkyne 120 sp -- sp 146 Allene 130 sp -- sp 143 sp -- sp 137 References Jump up ^ Handbook of Chemistry & Physics ( 65th ed. ). CRC Press. ISBN 0 - 8493 - 0465 - 2. Jump up ^ Fumio Toda ( April 2000 ). `` Naphthocyclobutenes and Benzodicyclobutadienes : Synthesis in the Solid State and Anomalies in the Bond Lengths ''. European Journal of Organic Chemistry. 2000 ( 8 ) : 1377 -- 1386. doi : 10.1002 / ( SICI ) 1099 - 0690 ( 200004 ) 2000 : 8 < 1377 : : AID - EJOC1377 > 3.0.CO ; 2 - I. Jump up ^ Novoa J.J. ; Lafuente P. ; Del Sesto R.E. ; Miller J.S. ( 2001 - 07 - 02 ). `` Exceptionally Long ( 2.9 Å ) C -- C Bonds between ( TCNE ) Ions : Two - Electron, Four - Center π -- π C -- C Bonding in π - ( TCNE ) ''. Angewandte Chemie International Edition. 40 ( 13 ) : 2540 -- 2545. doi : 10.1002 / 1521 - 3773 ( 20010702 ) 40 : 13 < 2540 : : AID - ANIE2540 > 3.0.CO ; 2 - O. Jump up ^ Lü J. - M. ; Rosokha S.V. ; Kochi J.K. ( 2003 ). `` Stable ( Long - Bonded ) Dimers via the Quantitative Self - Association of Different Cationic, Anionic, and Uncharged - Radicals : Structures, Energetics, and Optical Transitions ''. J. Am. Chem. Soc. 125 ( 40 ) : 12161 -- 12171. doi : 10.1021 / ja0364928. Jump up ^ Suzuki S. ; Morita Y. ; Fukui K. ; Sato K. ; Shiomi D. ; Takui T. ; Nakasuji K. ( 2006 ). `` Aromaticity on the Pancake - Bonded Dimer of Neutral Phenalenyl Radical as Studied by MS and NMR Spectroscopies and NICS Analysis ''. J. Am. Chem. Soc. 128 ( 8 ) : 2530 -- 2531. doi : 10.1021 / ja058387z. Jump up ^ Huntley D.R. ; Markopoulos G. ; Donovan P.M. ; Scott L.T. ; Hoffmann R. ( 2005 ). `` Squeezing C -- C Bonds ''. Angewandte Chemie International Edition. 44 ( 46 ) : 7549 -- 7553. doi : 10.1002 / anie. 200502721. PMID 16259033. Jump up ^ Martinez - Guajardo G. ; Donald K.J. ; Wittmaack B.K. ; Vazquez M.A. ; Merino G. ( 2010 ). `` Shorter Still : Compresing C -- C Single Bonds ''. Organic Letters, ASAP. 12 ( 18 ) : 4058. doi : 10.1021 / ol101671m. Jump up ^ Fox, Marye Anne ; Whitesell, James K. ( 1995 ). Organische Chemie : Grundlagen, Mechanismen, Bioorganische Anwendungen. Springer. ISBN 978 - 3 - 86025 - 249 - 9. External links Bond length tutorial Retrieved from `` https://en.wikipedia.org/w/index.php?title=Bond_length&oldid=865252614 '' Categories : Chemical bond properties Molecular geometry Length Talk Contents About Wikipedia Afrikaans Bosanski Català Deutsch Ελληνικά Español فارسی Français Bahasa Indonesia Italiano Magyar മലയാളം Nederlands 日本 語 Português Русский Српски / srpski Suomi ไทย Українська 中文 13 more Edit links This page was last edited on 22 October 2018, at 18 : 51 ( UTC ). Text is available under the Creative Commons Attribution - ShareAlike License ; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia ® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. About Wikipedia

Question: the carbon carbon bond length in benzene is
Answer: 139 pm