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

I D H Oswald, D R Allan, W D S Motherwell, S Parsons, C R Pulham, P.A. McGregor

Research output: Contribution to journalArticle

102 Citations (Scopus)

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 OH...O==C interactions [C(9) chains in graph-set notation] or NH...O==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.

Original languageEnglish
Pages (from-to)1057-1066
Number of pages10
JournalActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume58
Issue numberPart 6
DOIs
Publication statusPublished - Dec 2002

Keywords

  • polymorph
  • crystals

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