Abstract
The methods of electronic and vibrational (IR) spectroscopy were used to study the spectral properties of isocytosine in H2O, D2O, chloroform, and hexane in a wide concentration interval. Quantum chemical calculations of tautomeric forms and dimers of isocytosine were carried out. The bands of the calculated and experimental spectra were assigned. The results of the quantum calculations were compared with the experimental data. The spectral bands were classified according to the type of tautomer or dimer to which they belong.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
K. I. Yakovlev, A. I. Stetsenko, A. A. Tulub, et al., “Platinum (II) complexes with aminopyridines,” The Fifth International Symposium on Platinum and Other Coordination Compounds in Cancer Chemotherapy (Padua, June 29–July 2, 1987), Padua (1987), pp. 361–362.
C. B. Duke, “Electronic structure of large molecules,” Int. J. Quant. Chem. Symp., No. 13, 267–287 (1979).
B. D. Sharma and J. F. McConnell, “The crystal and molecular structure of isocytosine,” Acta Crystallogr.,19, No. 5, 797–806 (1965).
R. Stolarski, M. Remin, and D. Shugar, “Studies on prototropic tautomerism in neutral and monoanionic forms of pyrimidines by nuclear magnetic resonance spectroscopy,” Z. Naturforsch.,C32, No. 5, 894–900 (1977).
R. Czerminski, B. Lesyng, and B. Pohorille, “Tautomerism of pyrimidine bases — uracil, cytosine, isocytosine: theoretical study with complete optimization of geometry,” Int. J. Quant. Chem.,16, No. 3, 605–613 (1979).
S. G. Semenov, A. V. Tulub, V. L. Rapoport, et al., “The electronic structure of photoexcited states of cytosine molecule,” Khim. Fiz.,4, No. 1, 25–29 (1985).
L. G. Marzilli, “Metal complexes of nucleic acid derivatives and nucleosides: binding sites and structures,” in: Metal Ions in Genetic Information Transfer (Advances in Experimental Medicine and Biology, Vol. 40), G. L. Eichhorn and L. G. Marzilli (editors), Elsevier, New York (1981).
J. J. Roberts, “The mechanism of action of antitumor platinum coordination compounds,” ibid., pp. 274–332.
A. V. Borodavkin, E. I. Budovskii, Yu. V. Morozov, et al., “Electronic structure, UV absorption spectra, and reactivity of nucleic acid components,” Reviews of Science and Technology. Molecular Biology [in Russian], Vol. 14, VINITI, Moscow (1977).
N. P. Bazhulina, Yu. V. Morozov, F. A. Savin, et al., “Acid-base and tautomer equilibria, UV spectroscopic properties, and electronic structure of some purine analogs of nucleic bases,” Bioorg. Khim.,11, No.1, 49–59 (1985).
P. O. P. Ts'o, “Bases, nucleotides, and nucleosides,” in: Basic Principles in Nucleic Acid Chemistry, P. O. P. Ts'o (editor), Vol. 1, Academic Press, New York (1974), pp. 453–586.
M. Tsuboi, “Infrared and Raman spectra,” ibid., pp. 339–449.
Y. Kougoku, R. C. Lord, and A. Rich, “An infrared study of the hydrogen-bonding specificity of hypoxanthine and other nucleic acid derivatives,” Biochim. Biophys. Acta.,179. No. 1, 10–17 (1969).
L. J. Bellamy, The Infrared Spectra of Complex Molecules, Wiley, New York (1958).
Z. G. Kudritskaya and V. I. Danilov, “Quantum chemical study of bases interactions in various associates in atomic dipole approximation,” J. Theor. Biol.,59, No. 2, 303–319 (1976).
Author information
Authors and Affiliations
Additional information
Translated from Teoreticheskaya i éksperimental'naya Khimiya, Vol. 24, No. 1, pp. 29–36, January–February, 1988.
The authors are grateful to I. M. Ginzberg and L. F. Strelkova for their participation in the discussion of the infrared spectroscopy results.
Rights and permissions
About this article
Cite this article
Tulub, A.A., Semenov, S.G., Stetsenko, A.I. et al. Spectroscopic and quantum chemical studies of isocytosine. Theor Exp Chem 24, 26–32 (1988). https://doi.org/10.1007/BF01392186
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01392186