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Título: | The structure and properties of 5,6-dinitro-1H-benzotriazole |
Autor: | Santa María, Dolores; Claramunt, Rosa M.; Torralba, M. Carmen; Torres, M. Rosario; Alkorta, Ibon CSIC ORCID ; Elguero, José CSIC ORCID | Palabras clave: | X-ray structure CPMAS NMR GIAO/DFT calculations Pseudopolymorphism Benzotriazole Tautomerism |
Fecha de publicación: | 2016 | Editor: | Elsevier | Citación: | Journal of Molecular Structure 1113: 153-161 (2016) | Resumen: | 5,6-Dinitro-1H-benzotriazole crystallizes in the monoclinic system, space group P2/c. The asymmetric unit contains the planar 1H-tautomer together with a water molecule of crystallization. Each water molecule is hydrogen bonded to three adjacent 5,6-dinitrobenzotriazoles forming a tape along the b-axis of the crystal. These tapes stack along the c-axis through hydrogen bonds involving the water molecules and one of the nitro groups leading to a bidimensional structure. Solid-state C and N CPMAS NMR allow to confirm that the tautomer present is the 1H one. In DMSO-d solution the results are quite different and, based on GIAO/B3LYP/6-311++G(d,p) calculations, lead us to conclude that the major tautomer is the 5,6-dinitro-2H-benzotriazole, a surprising result that contradicts the rule that the major tautomer in solution coincides with the one present in the crystal. An anhydrous pseudopolymorph of 5,6-dinitro-1H-benzotriazole has been obtained as a non-crystalline form and from solid-state NMR and theoretical calculations, we conclude that it is an 1H-tautomer. | Versión del editor: | http://dx.doi.org/10.1016/j.molstruc.2016.02.020 | URI: | http://hdl.handle.net/10261/133040 | DOI: | 10.1016/j.molstruc.2016.02.020 | Identificadores: | doi: 10.1016/j.molstruc.2016.02.020 issn: 0022-2860 |
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