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From anisole to 1,2,4,5‐tetramethoxybenzene: Theoretical study of the factors that determine the conformation of methoxy groups on a benzene ring
Author(s) -
Velde Christophe Vande,
Bultinck Evi,
Tersago Karla,
Alsenoy Christian Van,
Blockhuys Frank
Publication year - 2006
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21183
Subject(s) - anisole , coplanarity , benzene , ring (chemistry) , chemistry , computational chemistry , series (stratigraphy) , quantum chemical , aromaticity , stereochemistry , preference , crystallography , molecule , organic chemistry , mathematics , geometry , catalysis , paleontology , statistics , biology
Unhindered ortho ‐dimethoxy‐substituted phenyl rings often display a coplanar conformation. A theoretical study of a series of methoxybenzenes consisting of methoxybenzene (anisole), the three dimethoxybenzenes, and 1,2,4,5‐tetramethoxybenzene, at the DFT/B3LYP/6‐311++G** level of theory, allows us to identify the factors influencing the conformational preference and attribute the coplanarity of such methoxy groups to mesomeric effects. © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2007