Title:Synthesis and Theoretical Study of a Series of 3,5-disubstitutes Pyrazoles
VOLUME: 17 ISSUE: 12
Author(s):Karine Braga Enes, Ana Clara Alves Branco, Maria Eduarda Toledo Lima, Marcella Fernandes Mano Mateus, Luciana Guimaráes, Clebio Soares Nascimento and Mara Rubia Costa Couri*
Affiliation:Nucleo de Estudos em Catalise e Síntese Organica (NECSO), Departamento de Quimica, ICE, Universidade Federal de Juiz de Fora, Campus Martelo, CEP 36036-330, Juiz de Fora, MG, Nucleo de Estudos em Catalise e Síntese Organica (NECSO), Departamento de Quimica, ICE, Universidade Federal de Juiz de Fora, Campus Martelo, CEP 36036-330, Juiz de Fora, MG, Nucleo de Estudos em Catalise e Síntese Organica (NECSO), Departamento de Quimica, ICE, Universidade Federal de Juiz de Fora, Campus Martelo, CEP 36036-330, Juiz de Fora, MG, Laboratorio de Quimica Teorica e Computacional (LQTC), Departamento de Ciencias Naturais, Universidade Federal de Sao Joao del-Rei, Campus Dom Bosco, Praca Dom Helvecio 74, Fabricas, 36301-160, Sao Joao del-Rei, Minas Gerais, Laboratorio de Quimica Teorica e Computacional (LQTC), Departamento de Ciencias Naturais, Universidade Federal de Sao Joao del-Rei, Campus Dom Bosco, Praca Dom Helvecio 74, Fabricas, 36301-160, Sao Joao del-Rei, Minas Gerais, Laboratorio de Quimica Teorica e Computacional (LQTC), Departamento de Ciencias Naturais, Universidade Federal de Sao Joao del-Rei, Campus Dom Bosco, Praca Dom Helvecio 74, Fabricas, 36301-160, Sao Joao del-Rei, Minas Gerais, Nucleo de Estudos em Catalise e Síntese Organica (NECSO), Departamento de Quimica, ICE, Universidade Federal de Juiz de Fora, Campus Martelo, CEP 36036-330, Juiz de Fora, MG
Keywords:Pyrazoles synthesis, theoretical calculations, density functional theory, quantum molecular descriptors.
Abstract:In this work, we proposed the synthesis of a series of pyrazoles derivatives with different
substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds
in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order
to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic
methodology, Density Functional Theory (DFT) calculations were performed. The reaction
Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some
selected reactants could explain qualitatively the experimental observations in terms of synthesis yield.
In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity
of the starting materials as well as the formation of the desired products.
