Four 1-aryl-1H-pyrazole-3,4-di­carboxyl­ate derivatives: synthesis, mol­ecular conformation and hydrogen bonding

Asma and Balakrishna, K. and Yathirajan, H. S. and Rathore, Ravindranath S. and Glidewell, Christopher (2018) Four 1-aryl-1H-pyrazole-3,4-di­carboxyl­ate derivatives: synthesis, mol­ecular conformation and hydrogen bonding. Acta Crystallographica Section E, 74 (12). pp. 1783-1789. ISSN 1600-5368

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Official URL: https://doi.org/10.1107/S2056989018015864

Abstract

Four 1-aryl-1H-pyrazole-3,4-di­carboxyl­ate derivatives, one acid, two esters and a dicarbohydrazide have been synthesized starting from 3-aryl sydnones, and structurally characterized. There is an intra­molecular O—H⋯O hydrogen bond in 1-phenyl-1H-pyrazole-3,4-di­carb­oxy­lic acid, C11H8N2O4, (I), and the mol­ecules are linked into a three-dimensional framework structure by a combination of O—H⋯O, O—H⋯N, C—H⋯O and C—H⋯π(arene) hydrogen bonds. In each of the two esters dimethyl 1-phenyl-1H-pyrazole-3,4-di­carboxyl­ate, C13H12N2O4, (II), and dimethyl 1-(4-methyl­phen­yl)-1H-pyrazole-3,4-di­carboxyl­ate, C14H14N2O4, (III), C—H⋯O hydrogen bonds lead to the formation of cyclic centrosymmetric dimers: in (III), one of the meth­oxy­carbonyl groups is disordered over two sets of atomic sites having occupancies 0.71 (2) and 0.29 (2). An intra­molecular N—H⋯O hydrogen bond is present in the structure of 1-(4-meth­oxy­phen­yl)-1H-pyrazole-3,4-dicarbohydrazide, C12H14N6O3, (IV), and the mol­ecules are linked into a three-dimensional framework structure by a combination of N—H⋯O, N—H⋯N, N—H⋯π(arene) and C—H⋯O hydrogen bonds. Comparisons are made with the structures of a number of related compounds.

Item Type: Article
Uncontrolled Keywords: synthesis, 1,3-dipolar addition, crystal structure, molecular conformation, disorder, hydrogen bonding, supramolecular assembly
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 12 Oct 2019 07:34
Last Modified: 12 Oct 2019 07:34
URI: http://eprints.uni-mysore.ac.in/id/eprint/8943

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