Abstract
The molecule of the salt consists of two quinine cations and a biphenyl 2,2′-dicarboxylic dianion. Both of the quinine cations are protonated at the nitrogen atoms of the quinuclidine fragments. Each carboxylic group of the diphenic dianion acts as a proton donor with respect to the quinuclidine N(1) atom of one of the quinine cations, and as a proton acceptor with respect to the carbinol O(12′)-H(12′) group of the other. Thus, the interlocking hydrogen-bond system forms a rigid structure. The molecular conformation around the C(8)-C(9) bond is synclinal. The conformational parameters of the diphenic dianion are considerably different from those of diphenic acid in solid state. The absolute configuration of the biphenyl 2,2′-dicarboxylic dianion (S) is defined by the positive torsion angle around the line which connects the centers of both phenyl rings. The molecular chirality of the salt arises from the coupling between the quinoline and the biphenyl chromophores, as well as from the coupling of the quinoline-quinoline long-axis polarizedβ-band transition moments.
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Cahn, R. S., Ingold, C. K., and Prelog, V. (1966)Angew. Chem. Int. Ed. Engl. 5, 385.
Carter, O. L., McPhail, A. T., and Sim, G. A. (1967)J. Chem. Soc. A, 365.
Dupont, L., Konsur, A., Lewiński, K., and Oleksyn, B. (1985)Acta Cryst. C 41, 616.
Fronczek, F. R., Davis, S. T., Gehring, L. M. B., and Gandour, R. D. (1987)Acta Cryst. C 43, 1615.
Gawroński, J., and Gawrońska, K. (1984)J. Chem. Res. (S), 304.
Gawroński, J., Brzostowska, M., and Koput, J. (1989)Croat. Chem. Acta 62, 97.
Gawroński, J., and Piwowar, D. (1989) Unpublished data.
Graham, D. W., Ashton, W. T., Barash, L., Brown, J. E., Canning, L. F., Chen, A., Springer, J. P., and Rogers, E. F. (1987)J. Med. Chem. 30, 1074.
Grethe, G., Lee, H. L., Mitt, T., and Uskoković, M. R. (1971)J. Am. Chem. Soc. 93, 5904.
Grethe, G., Lee, H. L., Mitt, T., and Uskoković, M. R. (1978a)J. Am. Chem. Soc. 100, 581.
Grethe, G., Lee, H. L., Mitt, T., and Uskokovic, M. R. (1978b)J. Am. Chem. Soc. 100, 589.
Gutzwiller, J., and Uskoković, M. R. (1978)J. Am. Chem. Soc. 100, 576.
Jacques, J., Collet, A., and Wilen, S. H. (1981)Enantiomers, Racemates and Resolutions, Wiley-Interscience, New York.
Jaskólski, M. (1982)Collected Abstracts of the Fourth Symposium on Organic Crystal Chemistry, Poznań, September 1982, edited by Z. Kałuski, pp. 70–71. A. Mickiewicz Univ., Poznań, Poland.
Johnson, C. K. (1976)OrtepII. ReportOrnl-5138. (Oak Ridge National Laboratory, Tenn.).
Kashino, S., and Haisa, M. (1983)Acta Cryst. C 39, 310.
Kharash, M. S., Senior, J. K., Stanger, D. W., and Chenicek, J. A. (1934)J. Am. Chem. Soc. 56, 1646.
Kuhn, R., and Albrecht, O. (1927)Annalen 455, 272.
Lehmann, M. S., and Larsen, F. K. (1974)Acta Cryst. A 30, 580.
Leser, J., and Rabinovich, D. (1978)Acta Cryst. B 34, 2260.
Lesslie, M. S., and Turner, E. E. (1934)J. Chem. Soc. 347.
Lightner, D. A., Gawroński, J. K., and Wijekoon, W. H. D. (1987)J. Am. Chem. Soc. 109, 6354.
Lyle, G. G., and Keefer, L. K. (1967)Tetrahedron 23, 3253.
Motherwell, W. D. S., and Clegg, W. (1978)Pluto78, program for drawing molecular and crystal structures (Univ. of Cambridge, Cambridge, England).
Nardelli, M. (1983)Comput. Chem. 7, 95.
Oleksyn, B. J., Stadnicka, K. M., and Hodorowicz, S. A. (1978)Acta Cryst. B 34, 811.
Oleksyn, B. J., Lebioda, L., and Ciechanowicz-Rutkowska, M. (1979)Acta Cryst. B 35, 440.
Oleksyn, B. J. (1982)Acta Cryst. B 38, 1832.
Ottersen, T. (1977)Acta Chem. Scand. Ser. A,31, 480.
Romming, C., Seip, H. M., and Oymo, I. A. (1974)Acta Chem. Scand. Ser. A 28, 507.
Sheldrick, G. M. (1976)Shelx76, program for crystal structure determination (University of Cambridge, Cambridge, England).
Sheldrick, G. M. (1986)ShelxS86, program for crystal structure determination (University of Cambridge, Cambridge, England).
Svendsen, J. S., Markó, I., Jacobsen, E. N., Rao, Ch. P., Bott, S., and Sharpless, K. B. (1989)J. Org. Chem. 54, 2264.
Uskoković, M. R., Henderson, T., Reese, C., Lee, H. L., Grethe, G., and Gutzwiller, J. (1978)J. Am. Chem. Soc. 100, 571.
Worsch, D., Vogtle, F., Kirfel, A., and Will, G. (1984)Naturwiss 71, 423.
Wynberg, H. (1986)Topics in Stereochemistry, Vol. 16, Eliel, E. L., Wilen, S. H., and Allinger, N. L., (eds) (Wiley, New York), pp. 87–129.
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Kubicki, M., Borowiak, T., Gawron, M. et al. Structure and molecular chirality of the 2∶1 salt of quinine with biphenyl 2,2′-dicarboxylic acid (diphenic acid). Journal of Crystallographic and Spectroscopic Research 20, 447–455 (1990). https://doi.org/10.1007/BF01180112
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DOI: https://doi.org/10.1007/BF01180112