Conformational stability of 2,2 '-dialkoxybenzpinacols in solid state

Citation
K. Matsumoto et al., Conformational stability of 2,2 '-dialkoxybenzpinacols in solid state, SUPRAMOL CH, 13(1), 2001, pp. 79-92
Citations number
23
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
SUPRAMOLECULAR CHEMISTRY
ISSN journal
1061-0278 → ACNP
Volume
13
Issue
1
Year of publication
2001
Pages
79 - 92
Database
ISI
SICI code
1061-0278(2001)13:1<79:CSO2'I>2.0.ZU;2-X
Abstract
X-ray analyses of the 2,2'-dialkoxybenzpinacols have established that the p reviously tentative assignment of configuration is incorrect. For ex-ample, the dl- and meso-isomer of 2,2'-dimethoxy-, 2,2'-diethoxy-, and 2,2'-dibut oxybenzyinacols proved to have a rigid conformation (1a alpha, 1b alpha, 1c alpha) and (1a beta, 1b beta, 1c beta) where hydroxy groups are always in an anti fashion, in the solid state, respettively. MM2 and semi-empirical m olecular orbital calculations for possible conformations were performed, su ggesting that the conformational stability of the present pinacols is contr olled by repulsive gauche interactions between aryl groups associated with intramolecular hydrogen bondings.