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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

1,* , 1, 2, 2 and 3
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 2-Arylbenzotriazoles; synthesis; NMR; X-ray analysis; DFT
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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