Homodimers of cytosine and 1-methylcytosine. A DFT study of geometry, relative stability and H-NMR shifts in gas-phase and selected solvents.

Jerzy Leszczyński, Guvanchmyrat Paytakov, Leonid Gorb, Andriy Stepanyugin, Svitlana Samiylenko, Dmytro Hovorun

Journal: Journal of molecular modeling 2014;20(3):2115

PMID: 24549791

Abstract

Dimers of cytosine and its N¹-methylated counterpart were investigated in gas-phase and in various solvents including chloroform, dimethylsulfoxide, and water. The studies were performed at DFT/M06-2X/6-31+G(d,p) level of theory. Relative stabilities of tautomers of cytosine solvated explicitly by a small number of solvent molecules were evaluated. Further solvation effect calculations for homodimers were carried out with conductor-like polarizable continuum model (CPCM). H-NMR shifts and IR frequencies for optimized structures were calculated and compared with available experimental data.

Address: Interdisciplinary Center for Nanotoxicity, Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS, 39217, USA.

DOI: 10.1007/s00894-014-2115-x

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MeSH Terms: Chloroform, Cytosine, Dimerization, Dimethyl Sulfoxide, Gases, Hydrogen Bonding, Isomerism, Magnetic Resonance Spectroscopy, Models, Molecular, Molecular Structure, Solvents, Thermodynamics, Water