Abstract
On the basis of a comparison of the protolysis constants and vibrational frequencies it is shown that intermolecular interactions are present in 6-substituted 9-(α,Ω-dihydroxyalkyl)-purines and the corresponding mono- and diphosphates. In addition, in the case of the phosphates the existence of intramolecular interactions of electrostatic character between the phosphate group and the heteroring is also proposed. A comparison of the protolysis constants provides evidence for the different character of the interaction of the dihydroxyalkyl residue with the heteroring of the base in series of adenine and hypoxanthine derivatives.
Similar content being viewed by others
Literature cited
S. A. Giller, I. N. Getsova, I. N. Goncharova, L. N. Petrulyanis, L. I. Mironova, G. F. Nazarova, and é. I. Bruk, Khim. Geterotsikl. Soedin., 1680 (1974).
S. A. Giller, I. N. Goncharova, I. N. Getsova, L. I. Mironova, é. I. Bruk, G. F. Nazarova, and L. N. Petrulyanis, Khim. Geterotsikl. Soedin., 1674 (1974).
Y. Clauwaert and Y. Z. Stockx, Naturforsch., 23b, 25 (1968).
A. Albert and D. J. Brown, J. Chem. Soc., 2060 (1954).
R. Phillips, Chem. Rev., 66, 501 (1966).
C. L. Angell, J. Chem. Soc., 504 (1961).
G. P. Zhizhina and é. F. Oleinik, Usp. Khim., 37, 474 (1972).
R. Bonaccorsi, A. Pullman, E. Scrocco, and J. Tomasi, Theor. Chim. Acta, 24, 51 (1972).
N. K. Kochetkov, é. I. Budovskii, E. D. Sverdlov, N. A. Simukova, M. F. Turchinskii, and V. I. Shibarev, The Organic Chemistry of Nucleic Acids [in Russian], Khimiya, Moscow (1970).
L. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971).
R. F. Stewart and L. H. Jensen, J. Chem. Phys., 40, 2071 (1964).
R. Phillips, S. J. P. Eisenberg, and R. J. Putman, J. Biol. Chem., 240, 4393 (1965).
M. Sundaralingam, Acta Cryst., 21, 495 (1966).
Y. Kyogoku, M. Tsuboi, and T. Shimanouchi, Nature, 189, 120 (1961).
M. Yu. Lidak, I. V. Dipan, R. A. Paegle, and Ya. P. Stradyn', Khim. Geterotsikl. Soedin., 708 (1972).
A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1962).
Author information
Authors and Affiliations
Additional information
See [1] for communication II.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1684–1689, December, 1974.
Rights and permissions
About this article
Cite this article
Giller, S.A., Goncharova, I.N., Getsova, I.N. et al. Analogs of purine nucleosides and purine mono- and polynucleotides. Chem Heterocycl Compd 10, 1481–1485 (1974). https://doi.org/10.1007/BF00474335
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00474335