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Nucleophilic Acyl Substitution of Acyl Diimides

journal contribution
posted on 2023-05-17, 02:04 authored by Amos, RIJ, Schiesser, CH, Jason SmithJason Smith, Brian YatesBrian Yates
(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.

History

Publication title

Journal of Organic Chemistry

Volume

74

Issue

15

Pagination

5707-5710

ISSN

0022-3263

Department/School

School of Natural Sciences

Publisher

Amer Chemical Soc

Place of publication

1155 16Th St, Nw, Washington, USA, Dc, 20036

Rights statement

Copyright 2009 American Chemical Society

Repository Status

  • Restricted

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Expanding knowledge in the chemical sciences

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