title: Structural studies of two Tinuvin P analogs: 2-(2,4-dimethylphenyl)-2H-benzotriazole and 2-phenyl-2H-benzotriazole.
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.
authors.affiliation: Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, 28040 Madrid, Spain. rclaramunt@ccia.uned.es
authors.forename: Rosa María
authors.initials: RM
authors.lastname: Claramunt
authors.forename: Dolores Santa
authors.initials: DS
authors.lastname: María
authors.forename: Elena
authors.initials: E
authors.lastname: Pinilla
authors.forename: M Rosario
authors.initials: MR
authors.lastname: Torres
authors.forename: José
authors.initials: J
authors.lastname: Elguero
mesh_terms: D002247:Carbon Isotopes; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009587:Nitrogen Isotopes; D011522:Protons; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C524702:2-(2,4-dimethylphenyl)-2H-benzotriazole; C524701:2-phenyl-2H-benzotriazole; D002247:Carbon Isotopes; D009587:Nitrogen Isotopes; D011522:Protons; D014230:Triazoles; C033674:benazol P