The structural properties of a noncentrosymmetric polymorph of 4-aminobenzoic acid

Acta Crystallogr C Struct Chem. 2014 Mar;70(Pt 3):323-5. doi: 10.1107/S2053229614002447. Epub 2014 Feb 22.

Abstract

The crystal structure of a polymorph of 4-aminobenzoic acid (PABA), C7H7NO2, at 100 K is noncentrosymmetric, as opposed to centrosymmetric in the structures of the other known polymorphs. The two crystallographically independent PABA molecules form pseudocentrosymmetric O-H...O hydrogen-bonded dimers that are further linked by N-H...O hydrogen bonds into a three-dimensional network. The benzene rings stack in the b direction. The CO2 moieties are bent out slightly from the benzene ring plane.

Keywords: 4-aminobenzoic acid; PABA; crystal structure; hydrogen bonding; noncentrosymmetric polymorph; pharmaceuticals; polymorphism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminobenzoic Acid / chemistry*
  • Crystallization
  • Hydrogen Bonding
  • Molecular Structure

Substances

  • 4-Aminobenzoic Acid