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

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Author(s): Rosa María Claramunt | Dolores Santa María | Elena Pinilla | M. Rosario Torres | José Elguero

Journal: Molecules
ISSN 1420-3049

Volume: 12;
Issue: 9;
Start page: 2201;
Date: 2007;
Original page

Keywords: 2-Arylbenzotriazoles | synthesis | NMR | X-ray analysis | DFT

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.
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