Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
7810077 | Journal of Molecular Structure | 2013 | 5 Pages |
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 NHâ¯O interactions to give a 2-dimensional sheet of classical hydrogen bonds. These sheets are further interconnected by NHâ¯Ï 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.
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Authors
Laura Cruickshank, Alan R. Kennedy, Norman Shankland,