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

A. Asma, Balakrishna Kalluraya, Hemmige S. Yathirajan*, Ravindranath S. Rathore, Christopher Glidewell

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1783-1789
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
Issue number12
DOIs
Publication statusPublished - 1 Dec 2018

Keywords

  • 1,3-dipolar addition
  • Crystal structure
  • Disorder
  • Hydrogen bonding
  • Molecular conformation
  • Supramolecular assembly
  • Synthesis

Fingerprint

Dive into the research topics of 'Four 1-aryl-1H-pyrazole-3,4-dicarboxylate derivatives: synthesis, molecular conformation and hydrogen bonding'. Together they form a unique fingerprint.

Cite this