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

Laura Cruickshank, Alan Kennedy, Norman Shankland

Research output: Contribution to journalArticle

4 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
LanguageEnglish
Pages132-136
Number of pages5
JournalJournal of Molecular Structure
Volume1051
Early online date2 Sep 2013
DOIs
Publication statusPublished - 5 Nov 2013

Fingerprint

Tyramine
Ionization
Dopamine
Hydrogen
Crystal structure
Phenethylamines
Crystallization
Phenol
Neurotransmitter Agents
Hydrogen bonds
Single crystals
X ray diffraction
Atoms

Keywords

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

Cite this

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Tautomeric and ionisation forms of dopamine and tyramine in the solid state. / Cruickshank, Laura; Kennedy, Alan; Shankland, Norman.

In: Journal of Molecular Structure , Vol. 1051, 05.11.2013, p. 132-136.

Research output: Contribution to journalArticle

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AU - Shankland, Norman

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