Anilinium monohydrogen DL-malate

Acta Crystallogr C. 2003 Dec;59(Pt 12):o709-11. doi: 10.1107/s0108270103023837. Epub 2003 Nov 30.

Abstract

Crystals of the title salt, [(C(6)H(5)NH(3))](+).[(HOOC(CH(2))CH(OH)COO)](-) or C(6)H(8)N(+).C(4)H(5)O(5)(-), are built up from protonated anilinium residues and monodissociated DL-malate ions. The NH(3)(+) group of the anilinium cation is ordered at room temperature. Rotation of the NH(3)(+) group along the C(aromatic)-Nsp(3) bond (often observed at room temperature in other anilinium salts) is prevented by N-H.O hydrogen bonds between the NH(3)(+) group and the malate anions. The anions are connected by four O-H.O hydrogen bonds into two-dimensional sheets parallel to the (001) plane. The charged moieties, i.e. the anilinium cations and the sheets of hydrogen-bonded malate anions, form two-dimensional layers in which the phenyl rings of the anilinium residues lie perpendicular to the malate-ion sheets. The conformation of the monodissociated malate ion in the crystal is compared with that obtained from ab initio molecular-orbital calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Crystallography, X-Ray
  • Ions
  • Malates / chemistry*
  • Models, Chemical
  • Models, Molecular
  • Protein Conformation
  • Salts / chemistry*
  • Temperature

Substances

  • Aniline Compounds
  • Ions
  • Malates
  • Salts
  • malic acid
  • aniline