EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.

Authors

  • Constain SALAMANCA M. Departamento de Farmacia. Facultad de Química Farmacéutica. Universidad de Antioquia.
  • William TIZNADO V. Departamento de Ciencias Químicas. Facultad de Ecología y Recursos Naturales. Universidad Nacional Andres Bello.
  • Paula JARAMILLO G. Instituto de Física. Faculdade de Ciências. Universidade de São Paulo

DOI:

https://doi.org/10.17533/udea.vitae.6345

Keywords:

chemical synthesis, theoretical study, nitroimidazoles.

Abstract

In this work we realized and experimental and theoretical study of the N-alkylation of nitroimidazoles.
The N-alkyl-2-methyl-nitroimidazoles correspond to biologically active molecules, obtained by reaction
of 2-methyl-5-nitroimidazole and different alkyl halides. This reaction showed the formation of a mixture
of isomeric products in different proportions, denominated like N-alkyl-2-methyl-4-nitroimidazole and
N-alkyl-2-methyl-5-nitroimidazole, respectively. The reaction suggestes the formation of a tautomeric
equilibrium, which generates two nucleophilic sites susceptible to electrophilic attack by the alkyl halide.
The local nucleophilic reactivity of the nitroimidazole ring is determined using local reactivity indices such
as the Fukui function and the electrostatic potential, besides the electronic localization function (ELF). The
Fukui function was integrated for each atom using partition schemes based on analysis of Mulliken charges
and natural bond orbital (NBO). Finally the reaction profiles were assessed. The results show a minor
difference in the local reactivity. Nevertheless a significant difference in energy barriers is observed explaining
the formation of an isomeric product over another. These results agree quite well with the experimental data.
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Published

28-07-2010

How to Cite

SALAMANCA M., C., TIZNADO V., W., & JARAMILLO G., P. (2010). EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES. Vitae, 17(2), 199–208. https://doi.org/10.17533/udea.vitae.6345

Issue

Section

Pharmaceutical Industry

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