Photoinduced amino-imino tautomerism: an infrared study of 2-amino-5-methylpyridine in a low-temperature argon matrix

J Phys Chem A. 2006 May 11;110(18):6016-22. doi: 10.1021/jp056290t.

Abstract

The photoreaction of 2-amino-5-methylpyridine was investigated by matrix-isolation infrared spectroscopy and DFT calculation. Photoinduced reversible amino (N=C-NH(2))-imino (NH-C=NH) tautomerism was found between 2-amino-5-methylpyridine and 5-methyl-2(1H)-pyridinimine; the amino tautomer changes to the imino tautomer by UV irradiation (340>lambda>or= 300 nm) and the reverse change occurs by longer-wavelength light irradiation (420>lambda>or= 340 nm). The results of the CASSCF calculation revealed that the amino-imino tautomerism proceeds in vibrational relaxation process from electronic excited state to the ground state. The IR spectra of 2-amino-5-methylpyridine in the T(1) state and 5-methyl-2-pyridinamino radical were also obtained by UV irradiation (lambda>or= 300 nm).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Aminopyridines / chemistry*
  • Argon / chemistry*
  • Imino Acids / chemistry*
  • Molecular Structure
  • Photochemistry
  • Spectrophotometry, Infrared
  • Stereoisomerism
  • Temperature

Substances

  • 2-amino-5-methylpyridine
  • Amino Acids
  • Aminopyridines
  • Imino Acids
  • Argon