A theoretical and experimental investigation of the electronic spectra and tautomerization of nucleobases.
The electronic structures of all possible tautomers of uracil, thymine, cytosine, adenine and guanine have been carefully examined within the MNDO-MO frame-work. Equilibrium geometries are determined and the relative stabilities are discussed. Allowance for solvent effect on the stabilities is made by assuming a tetrahedral solvent cage with the DNA base occupying its centre. The electronic absorption spectra of the studied DNA bases, in solvents of different polarities are recorded and discussed. Assignments of the observed bands are facilitated using MNDO-CI computations. It is suggested that in solution the DNA bases are in some statistical mixtures of the most stable tautomers, and the Watson-Crick (WC) structure cannot account for the observed spectra alone.
Alyoubi
A O
AO
Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 9028, Jeddah 21413, Saudi Arabia.
Hilal
R H
RH