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

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 reactionof 2-methyl-5-nitroimidazole and different alkyl halides. This reaction showed the formation of...

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Autores principales:	Constain SALAMANCA M., William TIZNADO V., Paula JARAMILLO G.
Formato:	article
Lenguaje:	EN
Publicado:	Universidad de Antioquia 2010
Materias:	chemical synthesis theoretical study nitroimidazoles. Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675
Acceso en línea:	https://doaj.org/article/ce46f8f1dd534be5a388406ad15f2a83
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spelling	oai:doaj.org-article:ce46f8f1dd534be5a388406ad15f2a832021-11-19T04:14:22ZEXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.0121-40042145-2660https://doaj.org/article/ce46f8f1dd534be5a388406ad15f2a832010-07-01T00:00:00Zhttps://revistas.udea.edu.co/index.php/vitae/article/view/6345https://doaj.org/toc/0121-4004https://doaj.org/toc/2145-2660In 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 reactionof 2-methyl-5-nitroimidazole and different alkyl halides. This reaction showed the formation of a mixtureof isomeric products in different proportions, denominated like N-alkyl-2-methyl-4-nitroimidazole andN-alkyl-2-methyl-5-nitroimidazole, respectively. The reaction suggestes the formation of a tautomericequilibrium, 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 suchas the Fukui function and the electrostatic potential, besides the electronic localization function (ELF). TheFukui function was integrated for each atom using partition schemes based on analysis of Mulliken chargesand natural bond orbital (NBO). Finally the reaction profiles were assessed. The results show a minordifference in the local reactivity. Nevertheless a significant difference in energy barriers is observed explainingthe formation of an isomeric product over another. These results agree quite well with the experimental data.Constain SALAMANCA M.William TIZNADO V.Paula JARAMILLO G.Universidad de Antioquiaarticlechemical synthesistheoretical studynitroimidazoles.Food processing and manufactureTP368-456Pharmaceutical industryHD9665-9675ENVitae, Vol 17, Iss 2 (2010)
institution	DOAJ
collection	DOAJ
language	EN
topic	chemical synthesis theoretical study nitroimidazoles. Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675
spellingShingle	chemical synthesis theoretical study nitroimidazoles. Food processing and manufacture TP368-456 Pharmaceutical industry HD9665-9675 Constain SALAMANCA M. William TIZNADO V. Paula JARAMILLO G. EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
description	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 reactionof 2-methyl-5-nitroimidazole and different alkyl halides. This reaction showed the formation of a mixtureof isomeric products in different proportions, denominated like N-alkyl-2-methyl-4-nitroimidazole andN-alkyl-2-methyl-5-nitroimidazole, respectively. The reaction suggestes the formation of a tautomericequilibrium, 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 suchas the Fukui function and the electrostatic potential, besides the electronic localization function (ELF). TheFukui function was integrated for each atom using partition schemes based on analysis of Mulliken chargesand natural bond orbital (NBO). Finally the reaction profiles were assessed. The results show a minordifference in the local reactivity. Nevertheless a significant difference in energy barriers is observed explainingthe formation of an isomeric product over another. These results agree quite well with the experimental data.
format	article
author	Constain SALAMANCA M. William TIZNADO V. Paula JARAMILLO G.
author_facet	Constain SALAMANCA M. William TIZNADO V. Paula JARAMILLO G.
author_sort	Constain SALAMANCA M.
title	EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
title_short	EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
title_full	EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
title_fullStr	EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
title_full_unstemmed	EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.
title_sort	experimental and theoretical study of shyntesis of n-alkyl-nitroimidazoles.
publisher	Universidad de Antioquia
publishDate	2010
url	https://doaj.org/article/ce46f8f1dd534be5a388406ad15f2a83
work_keys_str_mv	AT constainsalamancam experimentalandtheoreticalstudyofshyntesisofnalkylnitroimidazoles AT williamtiznadov experimentalandtheoreticalstudyofshyntesisofnalkylnitroimidazoles AT paulajaramillog experimentalandtheoreticalstudyofshyntesisofnalkylnitroimidazoles
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EXPERIMENTAL AND THEORETICAL STUDY OF SHYNTESIS OF N-ALKYL-NITROIMIDAZOLES.

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