Synthesis, structure, and isomerism of N-2,4-dinitrophenylbenzotriazoles |
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Authors: | M Dolores Santa María Rosa M Claramunt M Ángeles García |
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Institution: | a Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain b Instituto de Química Médica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain |
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Abstract: | Both isomers of N-(2′,4′-dinitrophenyl)benzotriazole, the 1(3)- and the 2-substituted, have been characterized and their reciprocal isomerism was studied. Cross-experiments in the presence of 5(6)-nitro-1H-benzotriazole proved that the isomerization of 2-(2′,4′-dinitrophenyl)-2H-benzotriazole into the 1-isomer occurs by an intermolecular mechanism. The reported reaction of 5(6)-nitro-1H-benzotriazole with 1-chloro-2,4-dinitrobenzene has been reexamined discovering that there is an error in the proportions of N-substituted isomers. A possible explanation for the observed isomerizations was proposed. Identification of all compounds by multinuclear magnetic resonance, including solid-state studies, has been achieved. |
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Keywords: | Benzotriazoles 2 4-Dinitrophenyl group migration Kinetics NMR GIAO/B3LYP/6-31G&lowast absolute shieldings B3LYP/6-31G&lowast &lowast stabilization energies |
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