The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors

Acta Crystallogr B. 2002 Dec;58(Pt 6):1057-66. doi: 10.1107/s0108768102015987. Epub 2002 Nov 28.

Abstract

The crystal structures of five hemiadducts of paracetamol with 1,4-dioxane, N-methylmorpholine, morpholine, N,N-dimethylpiperazine and piperazine and a related 1:1 adduct of paracetamol with 4,4'-bipyridine are described. All structures are characterized by the formation of chains of paracetamol molecules, which are linked via either OHtriplebondO=C interactions [C(9) chains in graph-set notation] or NHtriplebondO=C interactions [C(4) chains], depending on the presence or absence of substituent groups on the guest molecule. In all cases except for the morpholine and bipyridine adducts these chains are connected by hydrogen-bond interactions with the guest molecules, which reside on crystallographic inversion centres. In the bipyridine adduct this linkage also involves a pi-stacking interaction; in the morpholine adduct it is formed between the OH groups of two opposed paracetamol molecules. Most adducts (that with 4,4'-bipyridine is an exception) decompose on heating to give monoclinic paracetamol. This is the first systematic study of a series of co-crystals containing paracetamol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaminophen / chemistry*
  • Calorimetry, Differential Scanning
  • Crystallography, X-Ray
  • Hydrogen Bonding*
  • Morpholines / chemistry
  • Piperazine
  • Piperazines / chemistry

Substances

  • Morpholines
  • Piperazines
  • Piperazine
  • Acetaminophen
  • morpholine