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Geometric Aspects of Aromaticity: Interrelations between Intramolecular Hydrogen Bonds, Steric Effects and π‐Electron Delocalisation in Nitroanilines
Author(s) -
Majerz Irena,
Dziembowska Teresa
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000978
Subject(s) - intramolecular force , chemistry , planarity testing , steric effects , aromaticity , hydrogen bond , natural bond orbital , ring (chemistry) , benzene , molecule , computational chemistry , crystallography , stereochemistry , density functional theory , organic chemistry
The influence of intramolecular hydrogen bonds and steric hindrance on distortion from planarity of the benzene ring and its aromaticity is shown for a series of substituted 2,4,6‐trinitroanilines. The crystal structure geometry and thegeometry optimized at the B3LYP/6‐311++G** level are compared with analogues without intramolecular hydrogen bonds. The HOMA index and the parameter Δ P describing the distortion from planarity of the benzene ring were used to characterize the aromacity of the investigated molecules. NBO and AIM analysis were also applied.