Chemistry of the 2,5-Didehydropyridine Biradical:  Computational, Kinetic, and Trapping Studies toward Drug Design

A combined computation, kinetic, and trapping study of the 2,5-didehydropyridine biradical finds the hydrogen abstraction reaction to be tunable by protonation. The observation of small amounts of pyridine products in the thermolysis of a C,N-dialkynylimine, or azaenediyne, only when the reaction oc...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1998-01, Vol.120 (2), p.376-385
Main Authors: Hoffner, Johannes, Schottelius, Marc J, Feichtinger, Derek, Chen, Peter
Format: Article
Language:English
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Summary:A combined computation, kinetic, and trapping study of the 2,5-didehydropyridine biradical finds the hydrogen abstraction reaction to be tunable by protonation. The observation of small amounts of pyridine products in the thermolysis of a C,N-dialkynylimine, or azaenediyne, only when the reaction occurs in the presence of moderate amounts of protic acid, is consistent with qualitative theoretical predictions as well as ab initio calculations at the CASSCF and CASMP2 levels. The implication of these findings for a more selective antitumor agent is discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9730223