Theoretical study of structure of alkali metal cyanates and isocyanates and their related ion pair SN2 reactions

Journal of Computational Chemistry

Volumn 19, Issue 12, 1998, Pages 1325-1336

  Leung, Simon Shun Wang ^a   Streitwieser, Andrew ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Ambident; Cyanate; Ion pair; Isocyanate; SN2 reaction

Indexed keywords

EID: 0005907429     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(199809)19:12<1325::AID-JCC1>3.0.CO;2-K     Document Type: Article

References (31)

1. For reviews on synthesis and reactions of isocyanates and cyanates, see: S. Patai, Ed., The Chemistry of Cyanates and Their Thio Derivatives, John Wiley & Sons, New York, 1977.
2. O. A. Reutov, I. P. Beletskaya and A. L. Kurts, Ambident Anions, Consultants Bureau, New York, 1983.
3. D. Poppinger and L. Radom, J. Am. Chem. Soc., 100, 3674 (1978).
4. M. A. McAllister and T. A. Tidwell, J. Chem. Soc. Perkin Trans., 2, 2239 (1994).
5. P. W. Schultz, G. E. Leroi, and J. F. Harrison, Mol. Phys., 88, 217 (1996).
6. (a) S. Harder, A. Streitwieser, J. T. Petty, and P. v. R. Schleyer, J. Am. Chem. Soc., 117, 3253 (1995)
7. (b) A. Streitwieser, G. S-C. Choy, and F. Abu-Hasanayn, J. Am. Chem. Soc., 119, 5013 (1997).
8. M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, P. J. Fox, D. J. De Frees, J. Baker, J. P. Stewart, and J. A. Pople, Gaussian-92, Gaussian Inc., Pittsburgh, PA, 1992.
9. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. Cheeseman, R. T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. AlLaham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian-94, Gaussian Inc., Pittsburgh, PA, 1995.
10. Values for 3-21G* calculations are available from the authors by request.
11. C. Møller and M. S. Plesset, Phys. Rev., 46, 618 (1934).
12. (a) P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem., 98, 11623 (1994)
13. (b) A. D. Becke, J. Chem. Phys., 98, 5648 (1993)
14. (c) C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).
15. A. E. Reed, R. B. Weinstock, and F. Weinhold, J. Chem. Phys., 83, 735 (1985).
16. (a) J. Rannou, D. Legoff, and M. Chabanel, J. Chem. Res. Synop., 324 (1989)
17. (b) J. Rannou and M. Chabanel, J. Chem. Phys., 77, 201 (1980)
18. (c) J. Rannou, G. Massé, and M. Chabanel, C. R. Acad. Sci. (Series C), 287, 93 (1978).
19. (a) T. Veszprémi, T. Pasinszki, and M. Fehér, J. Am. Chem. Soc., 116, 6303 (1994)
20. (b) O. Squalli, M. C. Martins Costa, A. Cartier, and M. Chabanel, J. Mol. Struct. (Theochem), 303, 11 (1994).
21. (a) M. A. S. Goher, N. A. Al-Salem, and A. Mautner, Polyhedron, 15, 3575 (1996)
22. (b) T. Mallah, M. L. Boillot, O. Kahn, J. Gouteron, S. Jeannin, and Y. Jeannin, Inorg. Chem., 25, 3058 (1986)
23. (c) Y. M. Chow and D. Britton, Acta Crystallogr., B31, 1922 (1975)
24. (d) D. M. Duggan and D. N. Hendrickson, Inorg. Chem., 13, 2056 (1974).
25. (a) F. Effenberger, K. Drauz, S. Förster, and W. Müller, Chem. Berl., 114, 173 (1981)
26. (b) P. A. Argabright, B. L. Phillips, and C. H. DePuy, J. Org. Chem., 35, 2253 (1970)
27. (c) D. Martin, H-J. Niclas, and D. Habisch, Liebig's Ann., 727, 10 (1969)
28. (d) A. Holm and C. Wentrup, Acta Chem. Scand., 20, 2123 (1966)
29. (e) P. A. Argabright, B. L. Phillips, and C. H. DePuy, Tetrahed. Lett., 5033 (1968);
30. (f) P. A. Argabright, H. D. Rider, and R. Sieck, J. Org. Chem., 30, 3317 (1965).
31. T. Austad, L. B. Engemyr, and J. Songstad. Acta Chem. Scand., 25, 3535 (1971).