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Front. Chem. | doi: 10.3389/fchem.2018.00136

Conceptual DFT Study of the Local Chemical Reactivity of the Colored BISARG Melanoidin and its Protonated Derivative

Juan Frau1 and  Daniel Glossman-Mitnik2*
  • 1Departament of Chemistry, Universidad de les Illes Balears, Spain
  • 2Departamento de Medio Ambiente y Energía, Centro de Investigación en Materiales Avanzados, Mexico

This computational study assessed eight fixed RSH (range-separated hybrid) density functionals that include CAM-B3LYP, LC-ωPBE, M11, MN12SX, N12SX, ωB97, ωB97X, and ωB97XD related to the Def2TZVP basis sets together with the SMD solvation model in the calculation the molecular structure and reactivity properties of the BISARG intermediate melanoidin pigment (5-(2-(E)-(Z)-5-[(2-furyl)methylidene]-3-(4-acetylamino-4-carboxybutyl)-2-imino-1,3-dihydroimidazol-4-ylideneamino(E)-4-[(2-furyl)methylidene]-5-oxo-1H-imidazol-1-yl)-2-acetylaminovaleric acid) and its protonated derivative, BISARG(p). The chemical reactivity descriptors for the systems were calculated via the Conceptual Density Functional Theory. The choice of active sites applicable to nucleophilic, electrophilic as well as radical attacks were made by linking them with Fukui functions indices, electrophilic and nucleophilic Parr functions, and the condensed Dual Descriptor ∆f(r). The study found the MN12SX and N12SX density functionals to be the most appropriate in predicting the chemical reactivity of the molecular systems under study starting from the knowledge of the HOMO, LUMO and HOMO-LUMO gap energies.

Keywords: BISARG, Conceptual DFT, chemical reactivity, Dual descriptor, Parr functions

Received: 14 Feb 2018; Accepted: 09 Apr 2018.

Edited by:

Sam P. De Visser, University of Manchester, United Kingdom

Reviewed by:

Carles Curutchet, Universitat de Barcelona, Spain
Mark E. Casida, Université Grenoble Alpes, France  

Copyright: © 2018 Frau and Glossman-Mitnik. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Dr. Daniel Glossman-Mitnik, Centro de Investigación en Materiales Avanzados, Departamento de Medio Ambiente y Energía, Miguel de Cervantes 120, Complejo Industrial Chihuahua, Chihuahua, 31136, Chihuahua, Mexico, daniel.glossman@cimav.edu.mx