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Abstract
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All available conformers of tisopurine as an important
pharmaceutical molecule are optimized and frequency
calculations calculated at M06-2X/6-311 G(2d,2p) level of theory. These conformers are classified
in 22 different tautomers, tautomer Z showing the most
stable tautomer in the gas phase. Effects of four different
solvents on the most stable conformer of each tautomer is
calculated. Solvents cause stabilization of all conformers
and relative solvent stabilization is as follows: water >
DMSO > acetone > toluene. Energy profile for such stabilization
is illustrated and mechanism of proton transfer
studied at the same level of theory. Solvent-assisted proton
transfer performed when water and methanol used as solvents.
Results indicate that explicit solvent effect has much
more stabilization on tautomerization processes compared
to implicit solvent effect.
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