Molecules 2007, 12(9), 2201-2214; doi:10.3390/12092201
Article

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

Rosa María Claramunt 1,* email, Dolores Santa María 1 , Elena Pinilla 2 , M. Rosario Torres 2  and José Elguero 3
1 Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, 28040 Madrid, Spain 2 Departamento de Química Inorgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), 28040 Madrid, Spain 3 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.
Received: 11 September 2007; in revised form: 20 September 2007 / Accepted: 20 September 2007 / Published: 21 September 2007
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Abstract: 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.
Keywords: 2-Arylbenzotriazoles; synthesis; NMR; X-ray analysis; DFT

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MDPI and ACS Style

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.

AMA Style

Claramunt RM, María DS, Pinilla E, Torres MR, Elguero J. Structural Studies of Two Tinuvin® P Analogs: 2-(2,4-Dimethyl-phenyl)-2H-benzotriazole and 2-Phenyl-2H-benzotriazole. Molecules. 2007; 12(9):2201-2214.

Chicago/Turabian Style

Claramunt, Rosa M.; María, Dolores S.; Pinilla, Elena; Torres, M. R.; Elguero, José. 2007. "Structural Studies of Two Tinuvin® P Analogs: 2-(2,4-Dimethyl-phenyl)-2H-benzotriazole and 2-Phenyl-2H-benzotriazole." Molecules 12, no. 9: 2201-2214.

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