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Multinuclear magnetic resonance and molecular mechanics studies on the conformations and the dynamic behaviors of α‐alkyl‐substituted o ‐methoxybenzyl alcohols
Author(s) -
Suezawa Hiroko,
Wada Hajime,
Watanabe Hiroshi,
Yuzuri Tomoaki,
Sakakibara Kazuhisa,
Hirota Minoru
Publication year - 1997
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199712)10:12<925::aid-poc958>3.0.co;2-#
Subject(s) - chemistry , intramolecular force , substituent , alkyl , hydrogen bond , molecular mechanics , computational chemistry , resonance (particle physics) , rotation (mathematics) , stereochemistry , molecular dynamics , molecule , organic chemistry , physics , geometry , mathematics , particle physics
The conformations and the dynamic behaviors of α‐monoalkyl‐ and α,α‐dialkyl‐ o ‐methoxybenzyl alcohols are discussed on the basis of their 1 H, 13 C and 17 O NMR spectra and MM3 calculations. The conformations of α‐monoalkyl derivatives are shown to be different from those of α,α‐dialkyl derivatives and unfavorable to form intramolecular OH · · · O hydrogen bonds. The trends of substituent effects on the restricted rotation about the C ipso —C α bond could be reproduced fairly well by MM3 calculations. © 1997 John Wiley & Sons, Ltd.