From anisole to 1,2,4,5‐tetramethoxybenzene: Theoretical study of the factors that determine the conformation of methoxy groups on a benzene ring |
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| Authors: | Christophe Vande Velde Evi Bultinck Karla Tersago Christian Van Alsenoy Frank Blockhuys |
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| Affiliation: | 1. Department of Chemistry, University of Antwerp, Universiteitsplein 1, B‐2610 Wilrijk, Belgium;2. Department of Chemistry, University of Antwerp, Universiteitsplein 1, B‐2610 Wilrijk, BelgiumDepartment of Chemistry, University of Antwerp, Universiteitsplein 1, B‐2610 Wilrijk, Belgium |
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| Abstract: | 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 |
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| Keywords: | conformational analysis methoxybenzene density functional theory mesomeric effect intramolecular interactions |
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