Computational nanochemistry report on the oxicams - Conceptual DFT indices and chemical reactivity

Jorge Ignacio Martínez-Araya, Guillermo Salgado-Morán, Daniel Glossman-Mitnik

Resultado de la investigación: Article

19 Citas (Scopus)

Resumen

A density functional theory study of eight oxicams was carried out in order to determine their global and local reactivities. These types of reactivities were measured by means of global and local reactivity descriptors coming from the conceptual density functional theory. Net electrophilicity as a global reactivity descriptor and local hypersoftness as a local reactivity descriptor were the used tools to distinguish reactivity and selectivity among these oxicams. Globally, isoxicam presents the highest electron donating capacity; meanwhile, the highest electron accepting capacity is exhibited by droxicam. Locally, two oxicams present neither nucleophilic nor electrophilic relevant reactivity in their peripheral pyridine ring, droxicam and tenoxicam, so that their more reactive zones are found on the respective fused rings. Oxicams have been divided into two subgroups in order to facilitate the local analysis of reactivity. One group is characterized because their most important condensed values for local hypersoftnes are well-separated: 4-meloxicam, lornoxicam, meloxicam, and normeloxicam. Meanwhile, the opposite situation is found in droxicam, isoxicam, piroxicam, and tenoxicam. As a whole, the nucleophilic characteristic noticeably predominates in these eight oxicams instead of an electrophilic behavior, thus meaning a greater tendency to donate electrons rather than withdrawing them; a consequence of this behavior implies a favorable interaction with a hypothetical receptor bearing one or more electron acceptor functional groups rather than electron donor functional groups; this would imply a maximization of this interaction from the covalent point of view.

Idioma originalEnglish
Páginas (desde-hasta)6339-6351
Número de páginas13
PublicaciónJournal of Physical Chemistry B
Volumen117
N.º21
DOI
EstadoPublished - 30 may 2013

Huella dactilar

Chemical reactivity
Discrete Fourier transforms
tenoxicam
meloxicam
reactivity
Electrons
Functional groups
Density functional theory
Bearings (structural)
Piroxicam
electrons
Pyridine
density functional theory
rings
subgroups
pyridines
tendencies
selectivity
interactions
droxicam

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Surfaces, Coatings and Films

Citar esto

Martínez-Araya, Jorge Ignacio ; Salgado-Morán, Guillermo ; Glossman-Mitnik, Daniel. / Computational nanochemistry report on the oxicams - Conceptual DFT indices and chemical reactivity. En: Journal of Physical Chemistry B. 2013 ; Vol. 117, N.º 21. pp. 6339-6351.
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abstract = "A density functional theory study of eight oxicams was carried out in order to determine their global and local reactivities. These types of reactivities were measured by means of global and local reactivity descriptors coming from the conceptual density functional theory. Net electrophilicity as a global reactivity descriptor and local hypersoftness as a local reactivity descriptor were the used tools to distinguish reactivity and selectivity among these oxicams. Globally, isoxicam presents the highest electron donating capacity; meanwhile, the highest electron accepting capacity is exhibited by droxicam. Locally, two oxicams present neither nucleophilic nor electrophilic relevant reactivity in their peripheral pyridine ring, droxicam and tenoxicam, so that their more reactive zones are found on the respective fused rings. Oxicams have been divided into two subgroups in order to facilitate the local analysis of reactivity. One group is characterized because their most important condensed values for local hypersoftnes are well-separated: 4-meloxicam, lornoxicam, meloxicam, and normeloxicam. Meanwhile, the opposite situation is found in droxicam, isoxicam, piroxicam, and tenoxicam. As a whole, the nucleophilic characteristic noticeably predominates in these eight oxicams instead of an electrophilic behavior, thus meaning a greater tendency to donate electrons rather than withdrawing them; a consequence of this behavior implies a favorable interaction with a hypothetical receptor bearing one or more electron acceptor functional groups rather than electron donor functional groups; this would imply a maximization of this interaction from the covalent point of view.",
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Computational nanochemistry report on the oxicams - Conceptual DFT indices and chemical reactivity. / Martínez-Araya, Jorge Ignacio; Salgado-Morán, Guillermo; Glossman-Mitnik, Daniel.

En: Journal of Physical Chemistry B, Vol. 117, N.º 21, 30.05.2013, p. 6339-6351.

Resultado de la investigación: Article

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