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Structural Studies of Two Tinuvin® P Analogs: 2-(2,4-Dimethyl-phenyl)-2H-benzotriazole and 2-Phenyl-2H-benzotriazole

Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, 28040 Madrid, Spain
Departamento de Química Inorgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), 28040 Madrid, Spain
Instituto de Química Médica, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
Author to whom correspondence should be addressed.
Molecules 2007, 12(9), 2201-2214;
Received: 11 September 2007 / Revised: 20 September 2007 / Accepted: 20 September 2007 / Published: 21 September 2007
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2-(2,4-Dimethylphenyl)-2H-benzotriazole (1) has been synthesized in a three step procedure starting from 2,4-dimethyl-N-(2-nitrophenyl)benzamide via a 5-(2,4- dimethylphenyl)-1-(2-nitrophenyl)-1H-tetrazole intermediate. Its structure and those of Tinuvin® P and 2-phenyl-2H-benzotriazole (5) have been studied by multinuclear NMR (1H-, 13C- and 15N-) in solution and in the solid state. X-ray diffraction analysis of 1 and 5 allowed to us establish the molecular conformation around the single bond connecting the two aromatic systems, in agreement with the conclusions drawn from the NMR study. In the case of 1 ab initio geometry optimization was achieved at the Hartree-Fock HF/6- 31G** and DFT B3LYP/6-31G** levels. View Full-Text
Keywords: 2-Arylbenzotriazoles; synthesis; NMR; X-ray analysis; DFT 2-Arylbenzotriazoles; synthesis; NMR; X-ray analysis; DFT

Figure 1

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Claramunt, R.M.; María, D.S.; Pinilla, E.; Torres, M.R.; Elguero, J. Structural Studies of Two Tinuvin® P Analogs: 2-(2,4-Dimethyl-phenyl)-2H-benzotriazole and 2-Phenyl-2H-benzotriazole. Molecules 2007, 12, 2201-2214.

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