A structural comparison of salt forms of dopamine with the structures of other phenylethylamines

Kennedy, Alan R. and Cruickshank, Laura and Maher, Pamela and McKinnon, Zoe (2023) A structural comparison of salt forms of dopamine with the structures of other phenylethylamines. Acta Crystallographica Section C: Structural Chemistry, 79 (Part 1). pp. 386-394. ISSN 2053-2296 (https://doi.org/10.1107/s2053229623007696)

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Abstract

The structures of four salt forms of dopamine are reported. These are dopamine [2‐(3,4‐dihydroxyphenyl)ethan‐1‐aminium] benzoate, C8H12NO2+·C7H5O2−, I, dopamine 4‐nitrobenzoate, C8H12NO2+·C7H4NO4−, II, dopamine ethanedisulfonate, 2C8H12NO2+·C2H4O6S22−, III, and dopamine 4‐hydroxybenzenesulfonate monohydrate, C8H12NO2+·C6H5O4S−·H2O, IV. In all four structures, the dopamine cation adopts an extended conformation. Intermolecular interaction motifs that are common in the salt forms of tyramine can be found in related dopamine structures, but hydrogen bonding in the dopamine structures appear to be more variable and less predictable than for tyramine. Packing analysis discovered three dopamine‐containing groups of structures that can be described as isostructural with regards to the cation positions. Two of these groups contain both dopamine and tyramine species, and one of these is also highly variable in other ways too, containing anhydrous and hydrated forms, different anion types and ionized and neutral phenylethylamine species. As such, the group illustrates that packing behaviour can be robust and similar even where intermolecular interactions such as hydrogen bonds are very different.

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