On tautomerism of the cytosine molecule.

Abstract:

:Tautomerism of the cytosine molecule is discussed in connection with recent experimental matrix-isolation infrared spectroscopic measurements and recent ab initio calculations of relative stabilities of tautomers and of IR spectra for different tautomeric forms of the compound. Experimental IR spectra in the N-H and O-H stretching regions and in the C = O stretching region are presented for cytosine and for its several derivatives considered as model compounds. This experimental evidence, as well as the quantum-mechanical calculations (including both electron correlation and zero-point vibrational contributions), clearly indicate that two tautomers of cytosine, i.e. the amino-hydroxy and amino-oxo forms with the hydrogen atom at the N(1) position, exist in equilibrium when the cytosine molecule is isolated in an inert environment. The effect of the environment on the relative stabilities of several tautomers is also discussed briefly.

journal_name

Acta Biochim Pol

journal_title

Acta biochimica Polonica

authors

Kwiatkowski JS,Person WB,Szczepaniak K,Szczesniak M

subject

Has Abstract

pub_date

1987-01-01 00:00:00

pages

165-81

issue

2

eissn

0001-527X

issn

1734-154X

journal_volume

34

pub_type

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