Abstract
This article reviews common definitions of pyramidalization. An appraisal of the quantification of pyramidalization follows, and the formulation of a new measure of pyramidalization. The versatility of the new measure is tested using correlation with some molecular properties.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Mock, W. L.Tetrahedron Lett.,1972, 475
Radom, L.; Pople, J. A.; Mock, W. L.Tetrahedron Lett., 1972, 479.
Dunitz, J. D. InPerspectives in Structural Chemistry; Dunjtz, J. D., Ibers, J. A.; Eds. Wiley: New York,1968, Vol. 2, pp. 1–70.
de la Harpe, C.; Van Dorp, W. A.Ber. Deutsch. Chem. Ges. 1875,8, 1048.
Stezowski, J. J.; Hildenbrand, T.; Suissa, R. M.; Agranat, I.Struct. Chem. In press.
Shoham, G.; Cohen, S.; Suissa, R. M.; Agranat, I.In Molecular Structure: Chemical Reactivity and Biological Activity; Stezowski, J. J., Huang, J.-L., Saho, M.-C., Eds.; Oxford University Press: London, 1988, pp. 290–312.
Lee, J. S.; Nyurg, S. C.Acta Crystallgr., Sect. C,1985,41, 560.
Winshenker, N. M.; Greene, F. D.J. Am. Chem. Soc.,1979,101, 1340.
Borden, W. T.Chem. Rev.,1989,89, 1095.
Warner, P. M.Chem. Rev.,1989,89, 1063.
Szeimies, G. InReactive Intermediates; Abramovitch, R., Ed. Plenum Press: New York, 1983, Vol. 3, pp. 299–366.
Ermer, O.; Lifson, S.J. Am. Chem. Soc.,1973,95, 4121;
Ermer, O.Angew. Chem. Int. Ed. Eng.,1974,13, 604;
Ermer, O.Struct. Bonding,1976,27, 161;
Ermer, O.Z. Naturforsch., B: 1979,32, 837;
Ermer, O.Helv. Chim Acta,1981,64, 1902.
Greenberg, A.; Liebman, J. F.Strained Organic Molecules. Academic Press: New York, 1978.
Malriew, J.-P.; Trinquier, G.J. Am. Chem. Soc.,1989,111, 5916;
Trinquier, G.; Malriew, J.-P. InThe Chemistry of Double-Bonded Functional Groups; Patai, S., Ed., Wiley: New York,1989, Suppl. A, Vol. 2, pp. 1–52;
Trinquier, G.; Malriew, J.-P.J. Am. Chem. Soc.,1987,109, 5303.
Volland, W. V.; Davidson, E. R.; Borden, W. T.J. Am. Chem. Soc.,1979,101, 533.
Houk, K. N.; Rondan, N. G.; Brown, F. K.; Jorgensen, W. L.; Madura, J. D.; Spellmeyer, D. C.J. Am. Chem. Soc.,1983,105, 5980;
Houk, K. N.; Rondan, N. G.; Brown, F. K.Isr. J. Chem.,1983,23, 3.
Paquette, L. A.; Shen, C.-C.; Krause, J. A.J. Am. Chem. Soc.,1989,111, 2351;
A more recent reference is: Irngartinger, H.; Deuter, J.; Charumilind, P.; Paquette, L. A.J. Am. Chem. Soc.,1989,111, 9236.
Haddon, R. C.J. Am. Chem. Soc.,1987,109, 1676;
Haddon, R. C.Acc. Chem. Res.,1988,21, 243;
Haddon, R. C.J. Am. Chem. Soc.,1986,108, 2837;
Haddon, R. C.J. Phys. Chem.,1987,91, 3719;
Haddon, R. C.J. Mol. Str. (THEOCHEM),1988,169, 69.
Burgi, H. R.; Shefter, E.Tetrahedron,1975,31, 2976.
Haddon, R. C.; Scott, L. T.Pure Appl. Chem.,1986,58, 137.
Binkley, J. S.; Frisch, M. J.; DeFrees, D. J.; Raghavachari, K.; Whiteside, R. A.; Schiegal, H. B.; Fluder, E. M.; Pople, J. A.Gaussian 82. Department of Chemistry, Carnegie-Mellon University: Pittsburgh, PA.
Haddon, R. C.J. Am. Chem. Soc.,1990,112, 3385.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Radhakrishnan, T.P., Agranat, I. Measures of pyramidalization. Struct Chem 2, 107–115 (1991). https://doi.org/10.1007/BF00676621
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00676621