Angular group-induced bond alternation (AGIBA). Part 5 - Conformation dependence and additivity of the effect: structural studies of 3,5-dimethoxybenzaldehyde derivatives and related systems

Authors
Krygowski, TM Pindelska, E Anulewicz-Ostrowska, R Grabowski, SJ Dubis, AT
Citation
Tm. Krygowski et al., Angular group-induced bond alternation (AGIBA). Part 5 - Conformation dependence and additivity of the effect: structural studies of 3,5-dimethoxybenzaldehyde derivatives and related systems, J PHYS ORG, 14(6), 2001, pp. 349-354
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
ISSN journal
08943230 → ACNP
Volume
14
Issue
6
Year of publication
2001
Pages
349 - 354
Database
ISI
SICI code
0894-3230(200106)14:6<349:AGBA(P>2.0.ZU;2-Q
Abstract
X-ray structure analysis of 3,4,5-trimethoxybenzadehyde and 3,5-dimethoxy-4 -(1-bromoethoxy)benzaldehyde gave their molecular geometries which showed a vague AGIBA effect. To clarify the situation, nb initio optimizations at t he MP2/6-31G**: level of theory of 12 conformers of 1,3,5-trimethoxy-, 1,3- dimethoxy-5-formy-1,3-diformyl-5-methoxy- and 1,3,5-triformylbenzene deriva tives were carried out. The results support the occurrence of additive AGIB A effects, even if some weak interactions are possible between the methoxy and formyl groups. Copyright (C) 2001 John Wiley & Sons, Ltd.