Quantum-chemical calculations of the methylation of hydroxamic and thiohydroxamic acids with diazomethane

Chung Yu Yang, Hui Lung Chen, Jia Jen Ho

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Abstract

We made calculations about the methylation of both hydroxamic and thiohydroxamic acids with CH2N2. The potential-energy surfaces of several proposed pathways leading to possible site-selective products (N-methylated and O-methylated hydroximates) are presented. Our results agree satisfactorily with an experimental observation by Liguori et al. who found site selectivity in the formation of dimethylated products. Simultaneous deprotonation and methylation occurs in both forms (E and Z) of hydroxamic acid and thiohydroxamic acid, and the net energy barrier via this pathway is the smallest. In most corresponding processes the energy barriers are smaller for thiohydroxamic acid, and the Z-form has an energy barrier smaller than that of the E-form in both hydroxamic and thiohydroxamic acids.

Original languageEnglish
Pages (from-to)27-34
Number of pages8
JournalJournal of Molecular Structure: THEOCHEM
Volume778
Issue number1-3
DOIs
Publication statusPublished - 2006 Dec 11

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Keywords

  • Ab initio
  • CHN
  • Hydroxamic acid
  • Thiohydroxamic acids

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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