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Nucleophilic Acyl Substitution of Acyl Diimides

Citation

Amos, RIJ and Schiesser, CH and Smith, Jason and Yates, BF, Nucleophilic Acyl Substitution of Acyl Diimides, Journal of Organic Chemistry, 74, (15) pp. 5707-5710. ISSN 0022-3263 (2009) [Refereed Article]

Copyright Statement

Copyright 2009 American Chemical Society

DOI: doi:10.1021/jo900923m

Abstract

(Figure Presented) The nucleophilic acyl substitution of the acyl diimide intermediate formed by the oxidation of isoniazid was found to involve two methanol molecules in a six-membered cyclic transition state. Calculations were performed in the gas phase at the B3LYP/6-311 + G(d,p)//B3LYP/6-31G(d) level of theory and solvation effects were included both explicitly and implicitly by using CPCM. The effect of electron withdrawing and donating groups on the aryl ring was also explored. The results obtained are in good agreement with experimental observations for the oxidation of isoniazid. © 2009 American Chemical Society.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Free Radical Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:Amos, RIJ (Dr Ruth Amos)
Author:Smith, Jason (Associate Professor Jason Smith)
Author:Yates, BF (Professor Brian Yates)
ID Code:62397
Year Published:2009
Web of Science® Times Cited:3
Deposited By:Chemistry
Deposited On:2010-03-11
Last Modified:2015-11-04
Downloads:0

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