Tautomeric and ionisation forms of dopamine and tyramine in the solid state

Laura Cruickshank, Alan Kennedy, Norman Shankland

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Crystallisation of the phenylethylamine neurotransmitter dopamine from basic aqueous solution yielded the 3-phenoxide Zwitterionic tautomer, despite this being a minority form in the solution state. In the crystal structure, dopamine has a dimeric [OCCOH]2 hydrogen bonded catechol motif that expands through Nsingle bondH⋯O interactions to give a 2-dimensional sheet of classical hydrogen bonds. These sheets are further interconnected by Nsingle bondH⋯π interactions. The structurally related base tyramine crystallises under similar conditions as a hemihydrate with all four possible species of tyramine present (cationic, anionic, Zwitterionic and neutral) in the crystal structure. Single crystal X-ray diffraction studies at 121 and 293 K showed dynamic hydrogen atom disorder for the phenol/phenoxide group, suggesting that the tyramine speciation observed arises from a solid-state process
Original languageEnglish
Pages (from-to)132-136
Number of pages5
JournalJournal of Molecular Structure
Volume1051
Early online date2 Sep 2013
DOIs
Publication statusPublished - 5 Nov 2013

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Keywords

  • tautomeric
  • ionisation
  • dopamine
  • tyramine
  • solid state
  • zwitterion
  • tautomerism
  • microspeciation
  • neurotransmitter

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