title: Nucleophilic acyl substitution of acyl diimides.
abstract: 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.
authors.affiliation: School of Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania 7001, Australia.
authors.forename: Ruth I J
authors.initials: RI
authors.lastname: Amos
authors.forename: Carl H
authors.initials: CH
authors.lastname: Schiesser
authors.forename: Jason A
authors.initials: JA
authors.lastname: Smith
authors.forename: Brian F
authors.initials: BF
authors.lastname: Yates
mesh_terms: D003198:Computer Simulation; D003500:Cyclization; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical
chemical_list: D007094:Imides; D000432:Methanol