Synthesis and Theoretical Study of a Series of 3,5-disubstitutes Pyrazoles

Author(s): Karine Braga Enes, Ana Clara Alves Branco, Maria Eduarda Toledo Lima, Marcella Fernandes Mano Mateus, Luciana Guimaráes, Clebio Soares Nascimento, Mara Rubia Costa Couri*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 12 , 2020


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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.

Keywords: Pyrazoles synthesis, theoretical calculations, density functional theory, quantum molecular descriptors.

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Article Details

VOLUME: 17
ISSUE: 12
Year: 2020
Published on: 08 December, 2020
Page: [932 - 938]
Pages: 7
DOI: 10.2174/1570178617666200409095632
Price: $65

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