Syntheses and crystal structures of four 4-(4-nitro-phenyl)piperazinium salts with hydrogen succinate, 4-aminobenzoate, 2-(4-chlorophenyl)acetate and 2,3,4,5,6-pentafluorobenzoate anions

Vinaya, Yeriyur B. Basavaraju, Hemmige S. Yathirajan, Sean Parkin

Research output: Contribution to journalArticlepeer-review

Abstract

The syntheses and crystal structures are presented for four organic salts of the 4-(4-nitrophenyl)piperazinium cation, namely, 4-(4-nitrophenyl)piperazinium hydrogen succinate, C10H14N3O2+․C4H5O4 (I), 4-(4-nitrophenyl)piperazinium 4-aminobenzoate monohydrate, C10H14N3O2+․C7H6NO2․H2O (II), 4-(4-nitro-phenyl)piperazinium 2-(4-chlorophenyl)acetate, C10H14N3O2+․C8H6ClO2 (III) and 4-(4-nitrophenyl)piperazinium 2,3,4,5,6-pentafluorobenzoate, C10H14N3O2+․C7F5O2 (IV). The salts form from mixtures of N-(4-nitrophenyl)piperazine and the corresponding acid [succinic acid (I), 4-aminobenzoic acid (II), 2-(4-chlorophenyl)acetic acid (III) and 2,3,4,5,6-pentafluorobenzoic acid (IV)] in mixed solvents of methanol and ethyl acetate. Salts I, III, and IV are anhydrous, whereas II is a monohydrate. In each structure, the overall conformation of the cation is determined by the disposition of the exocyclic N—C bond of the piperazine ring (either axial or equatorial) and twists about the N—C bond between the piperazine ring and its attached 4-nitrophenyl ring. The packing motifs in each structure are quite different, though all are dominated by strong N—H․ ․ ․O hydrogen bonds, which are augmented in I and II by O—H․ ․ ․O hydrogen bonds, and in III by a π–π stacking interaction between inversion-related 4-nitrophenyl groups.

Original languageEnglish
Pages (from-to)151-156
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume79
Issue numberPt 3
DOIs
StatePublished - Feb 9 2023

Bibliographical note

Publisher Copyright:
© 2023 International Union of Crystallography. All rights reserved.

Keywords

  • crystal structure
  • crystal structure
  • piperazinium salt
  • symmetrical hydrogen bond

ASJC Scopus subject areas

  • General Chemistry
  • General Materials Science
  • Condensed Matter Physics

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