Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5418021 | Journal of Molecular Structure: THEOCHEM | 2007 | 9 Pages |
Abstract
The rotational transition state in the isomerization of the syn- to anti-conformer for the parent and substituted benzoic acids has been characterized and the decarboxylation mechanism for these acids has been determined. A previously unreported intermediate in the salicylic acid decarboxylation pathway has been observed, demonstrating that there is a change in the reaction mechanism when the ortho-group participates in the development of the transition state. The intermediate, in a shallow well, has a keto-like structure. While salicylic acid reacts through the keto-like intermediate, other substituted benzoic acids, including 2-aminobenzoic acid, follow the previously reported direct mechanism.
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Authors
Krum Chuchev, Joseph J. BelBruno,