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

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Cruickshank, Laura and Kennedy, Alan and Shankland, Norman (2013) Tautomeric and ionisation forms of dopamine and tyramine in the solid state. Journal of Molecular Structure, 1051. pp. 132-136. ISSN 0022-2860 (https://doi.org/10.1016/j.molstruc.2013.08.002)

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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

ORCID iDs

Cruickshank, Laura, Kennedy, Alan ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Shankland, Norman;
CORE (COnnecting REpositories)