Hydrogen bonds and π–π interactions in two new crystalline phases of methylene blue
| Autor: | Giovanni Predieri, Claudia Graiff, Stefano Canossa |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
crystal structure
chloride bisulfite Stacking π–π interactions 02 engineering and technology Crystal structure 010402 general chemistry 01 natural sciences Chloride Research Communications lcsh:Chemistry Phase (matter) medicine bisulfite Hirshfeld surface analysis General Materials Science Ene reaction Hydrogen bond Chemistry Cationic polymerization methylene blue General Chemistry hydrogen bonding 021001 nanoscience & nanotechnology Condensed Matter Physics Acceptor 0104 chemical sciences Crystallography lcsh:QD1-999 π–π interactions methylene blue 0210 nano-technology medicine.drug |
| Zdroj: | Acta Crystallographica Section E: Crystallographic Communications, Vol 74, Iss 5, Pp 587-593 (2018) Acta Crystallographica Section E: Crystallographic Communications |
| ISSN: | 2056-9890 |
| DOI: | 10.1107/s2056989017017881 |
| Popis: | Two unprecedented solid phases of methylene blue (MB +), viz. 3,7-bis(dimethylamino)phenothiazin-5-ium chloride dihydrate and 3,7-bis(dimethylamino)phenothiazin-5-ium bisulfite, have been obtained and structurally characterized. The effective absence of hydrogen-bond donors in the second compound has important consequences on the stacking geometry and supramolecular interactions of the MB+ ions, which are analysed by Hirshfeld fingerprint plots. Two unprecedented solid phases involving the 3,7-bis(dimethylamino)phenothiazin-5-ium cation, i.e. methylene blue (MB+), have been obtained and structurally characterized. In the crystals of 3,7-bis(dimethylamino)phenothiazin-5-ium chloride dihydrate, C16H18N3S+·Cl−·2H2O (I) and 3,7-bis(dimethylamino)phenothiazinium bisulfite, C16H18N3S+·HSO4 − (II), the cationic dye molecules are planar and disposed in an antiparallel mode, showing π–π stacking interactions, with mean interplanar distances of 3.326 (4) and 3.550 (3) Å in (I) and (II), respectively. In compound (I), whose phase was found affected by merohedral twinning [BASF = 0.185 (3)], the presence of water molecules allows a network of hydrogen bonds involving MB+ as both a donor and an acceptor, whereas in compound (II), the homo-interaction of the anions causes an effective absence of classical hydrogen-bond donors. This substantial difference has important consequences for the stacking geometry and supramolecular interactions of the MB+ cations, which are analysed by Hirshfeld fingerprint plots and subsequently discussed. |
| Databáze: | OpenAIRE |
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