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

Chung Yu Yang, Hui Lung Chen, Jia-Jen Ho

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

We made calculations about the methylation of both hydroxamic and thiohydroxamic acids with CH 2 N 2 . 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

Fingerprint

Diazomethane
Hydroxamic Acids
methylation
Methylation
Energy barriers
acids
Potential energy surfaces
Deprotonation
Acids
Observation
products
energy
selectivity
potential energy
methylidyne

Keywords

  • Ab initio
  • CH N
  • Hydroxamic acid
  • Thiohydroxamic acids

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Cite this

Quantum-chemical calculations of the methylation of hydroxamic and thiohydroxamic acids with diazomethane. / Yang, Chung Yu; Chen, Hui Lung; Ho, Jia-Jen.

In: Journal of Molecular Structure: THEOCHEM, Vol. 778, No. 1-3, 11.12.2006, p. 27-34.

Research output: Contribution to journalArticle

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