Solvatochromism of Heteroaromatic Compounds: XX. 4(5)-Nitroimidazole |
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Authors: | Vokin A I Sherstyannikova L V Krivoruchka I G Aksamentova T N Krylova O V Turchaninov V K |
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Institution: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia |
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Abstract: | 4(5)-Nitroimidazole in solution is stabilized as the 5-nitro isomer due to formation of hydrogen bond with an aprotic protophilic solvent. Amphiprotic medium favors displacement of the tautomeric equilibrium toward the 4-nitro isomer via formation of a solvate complex where 4-nitroimidazole acts as hydrogen bond acceptor. The observed specific solvatochromic effect in the UV spectrum of 4-nitroimidazole and related heterocyclic nitro compounds is determined by the electronic configuration of the excited , *-state. |
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