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C−C Bond Variation in the 1‐Phenyl‐ o ‐carborane: Steric versus Electronic Effects
Author(s) -
Glukhov Ivan V.,
Antipin Mikhail Yu.,
Lyssenko Konstantin A.
Publication year - 2004
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200300743
Subject(s) - chemistry , antibonding molecular orbital , carborane , steric effects , ring (chemistry) , molecule , hydrogen bond , bond length , computational chemistry , crystallography , stereochemistry , atomic orbital , organic chemistry , physics , quantum mechanics , electron
Using the “Atoms in molecules” topological theory the nature of the C carb −C carb bond variation in 1‐phenyl‐ o ‐carborane upon rotation of the phenyl ring was investigated within B3LYP/6‐31G** calculations. Despite the low barrier to the rotation of the phenyl ring, the bond paths linking hydrogen atoms of the phenyl ring and the ones of the carborane cage were found for all conformations. The length of the C carb −C carb bond increases by 0.031 Å without large energetic inputs due to back‐donation of the π‐density of the phenyl ring to the antibonding C carb −C carb orbital. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)