Abstract
The crystal structures of threo(RR,SS) diethyl ester of 2-hydroxy-1,2-diphenylethylphosphonic acid (1) and of (±)diethyl ester of (1-hydroxycyclopentyl)(2-methylphenyl)methylphosphonic acid (2) have been solved by X-ray methods. They are built up in a similar way to centrosymmetric dimers of hydrogen-bonded molecules. The orientation of the substituents around the central C-C bond in both molecules fulfills the requirement for the least spatial hindrance. The observed shift of theυ oh stretching frequencies from 3312(1), 3346 (2) cm−1 in solid to 3408(1), 3450(2), in diluted (10−3 M) tetrachloromethane solution, indicates the formation of intramolecular hydrogen-bonded species.
Similar content being viewed by others
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G., and Taylor, R. (1987)J. Chem. Soc., Perkin Trans. 2, S1.
Boeyens, J. C. A., and Evans, D. G. (1989)Acta Crystallogr. B 45, 577.
Bottin-Strzalko, T., and Seyden-Penne, J. (1984)Bull. Soc. Chim. Fr. 2, 161.
Buss, A. D., Cruse, W. B., Kennard, O., and Warren, S. (1984)J. Chem. Soc. Perkin Trans. 1, S243.
Buss, A. D., and Warren, S. (1981)J. Chem. Soc. Chem. Commun. 100.
Corey, E. J., and Kwiatkowski, G. T. (1966)J. Am. Chem. Soc. 88, 5652.
Deschamps, B., Lefebvre, G., and Seyden-Penne, J. (1972)Tetrahedron. 28, 4209.
Enraf-Nonius (1985)Structure determination package, SDP/PDP V3.0 users guide. (Enraf-Nonius, Delft, The Netherlands).
Evans, D. G., and Boeyens, J. C. A. (1989)Acta Crystallogr. B 45, 581.
Horner, L., Hoffmann, H., Wippel, H. G., and Klahre, G. (1959)Chem. Ber. 92, 2499.
Kirilov, M., and Petrova, J. (1970)Chem. Ber. 103, 1047.
Main, P., Fiske, S. J., Hill, S. E., Lessinger, L., Germain, G., Declercq, J.-P., and Woolfson, M. M. (1982)MULTAN 11/82 A system of computer programs for the automatic solution of crystal structures from X-ray diffraction data. (University of York, York, England).
Petrova, J., Kirilov, M., and Momchilova, S. (1983)Phosph. Sulf. 17, 29.
Petrova, J., Vassilev, N. G., and Kirilov, M. (1990)Phosph. Sulf. 47, 457.
Shkolnikova, L. M., Masyuk, A. A., Polyanchuk, G. V., Krinitskaya, L. V., Afonin, E. G., Pechurova, N. I., and Dyatlova, I. M. (1989)Koord. Khim. 15, 486.
Spassov, S. L., Petrova, J., and Kirilov, M. (1982)J. Mol. Struct. 84, 91.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Angelova, O., Macicek, J., Vassilev, N.G. et al. Structures of threo(RR,SS) diethyl ester of 2-hydroxy-1,2-diphenylethylphosphonic acid and (±)diethyl ester of (1-hydroxycyclopentyl)(2-methylphenyl)methylphosphonic acid. Journal of Crystallographic and Spectroscopic Research 22, 253–258 (1992). https://doi.org/10.1007/BF01199525
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01199525