Structural studies of two Tinuvin P analogs: 2-(2,4-dimethylphenyl)-2H-benzotriazole and 2-phenyl-2H-benzotriazole

Molecules. 2007 Sep 21;12(9):2201-14. doi: 10.3390/12092201.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nitrogen Isotopes
  • Protons
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*

Substances

  • 2-(2,4-dimethylphenyl)-2H-benzotriazole
  • 2-phenyl-2H-benzotriazole
  • Carbon Isotopes
  • Nitrogen Isotopes
  • Protons
  • Triazoles
  • benazol P