Theoretical study of the ground and excited states of 7-methyl guanine and 9-methyl guanine: comparison with experiment

Phys Chem Chem Phys. 2006 Jul 14;8(26):3059-65. doi: 10.1039/b601629d. Epub 2006 May 9.

Abstract

The keto-enol tautomerization of 7-methyl-guanine and 9-methyl-guanine in the excited state was investigated using the time-dependent DFT (TDDFT) method. For both species, the potential energy surfaces of the ground state and two lowest singlet excited states (due to pi-->pi* and n-->pi* transitions) have been investigated and their features discussed in terms of consequences on the excited state dynamics. The findings suggest that, for both species, the state due to the n-->pi* transition, suspected to be an intermediate in the excited state deactivation, exhibits two minima with the second minimum characterized by an elongated N1-H distance. This structure, intermediate between enol and keto tautomers, might play a role in the excited state relaxation. The existence of this second well, however, is observed in both 7- and 9-methyl-guanine, which suggests that it cannot account alone for the different photophysical behavior of these species.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Computer Simulation
  • Guanine / analogs & derivatives*
  • Guanine / chemistry
  • Models, Chemical*
  • Models, Molecular*
  • Molecular Conformation

Substances

  • 9-methylguanine
  • Guanine
  • 7-methylguanine