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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
Author(s) -
Krygowski Tadeusz M.,
Pindelska Edyta,
AnulewiczOstrowska Romana,
Grabowski Sławomir J.,
Dubis Alina T.
Publication year - 2001
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/poc.376
Subject(s) - chemistry , additive function , conformational isomerism , benzaldehyde , computational chemistry , ab initio , group (periodic table) , stereochemistry , molecule , organic chemistry , mathematical analysis , mathematics , catalysis
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, ab initio optimizations at the MP2/6–31G** level of theory of 12 conformers of 1,3,5‐trimethoxy‐, 1,3‐dimethoxy‐5‐formyl‐, 1,3‐diformyl‐5‐methoxy‐ and 1,3,5‐triformylbenzene derivatives were carried out. The results support the occurrence of additive AGIBA effects, even if some weak interactions are possible between the methoxy and formyl groups. Copyright © 2001 John Wiley & Sons, Ltd.