Interconversion and reactions of in- and out-isomers of a triarylphosphine-containing cyclophane

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 12082-12087

  Chen, Yen Ting ^a   Baldridge, Kim K ^b   Ho, Douglas M ^a   Pascal Jr , Robert A ^a  

^a PRINCETON UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CYCLOPHANE; SILANE DERIVATIVE; SULFUR; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL REACTION; CONFORMATION; CRYSTAL STRUCTURE; HEATING; ISOMERISM; MOLECULAR DYNAMICS; SULFATION; X RAY CRYSTALLOGRAPHY;

EID: 0000730371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993503h     Document Type: Article

References (28)

1. For a comprehensive review of in/out isomerism, see: Alder, R. W.; East, S. P. Chem. Rev. 1996, 96, 2097-2111.
2. (a) Pascal, R. A., Jr.; Grossman, R. B. J. Org. Chem. 1987, 52, 4616-4617.
3. (b) Pascal, R. A., Jr.; Grossman, R. B.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 6878-6880.
4. (c) Pascal, R. A., Jr.; Winans, C. G.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 3007-3010.
5. (a) Pascal, R. A., Jr.; West, A. P., Jr.; Van Engen, D. J. Am. Chem. Soc. 1990, 112, 6406-6407.
6. (b) L'Esperance, R. P.; West, A. P., Jr.; Van Engen, D.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1991, 113, 2672-2676.
7. (c) West, A. P., Jr.; Smyth, N.; Kraml, C. M.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1993, 58, 3502-3506.
8. (a) Dell, S.; Vogelaar, N. J.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6421-6422.
9. (b) Dell, S.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1999, 64, 5626-5633.
10. Baechler, R. D.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 3090-3093.
11. As is shown later, when additional conformations of 1 and 2 are taken into account, the AM1 difference grows to 2.4 kcal/mol (Table 1), still a very small value.
12. Barnett, L.; Ho, D. M.; Baldridge, K. K.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1999, 121, 727-733.
13. Bartlett, P. D.; Meguerian, G. J. Am. Chem. Soc. 1956, 78, 3710-3715.
14. Davis, R. E. J. Phys. Chem. 1959, 63, 307-309.
15. Zon, G.; DeBruin, K. E.; Naumann, K.; Mislow, K. J. Am. Chem. Soc. 1969, 91, 7023-7027.
16. 1 conformation, indicating that other, low-symmetry conformations are accessible.
17. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
18. Sheldrick, G. M. SHELXTL Version 5; Siemens Analytical X-ray Instruments: Madison, Wisconsin, 1996.
19. Van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, 194-201.
20. Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, C34.
21. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519.
22. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
23. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; John Wiley & Sons: New York, 1986; pp 63-100.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1998.
25. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Elbert, S. T. J. Comput. Chem. 1993, 14, 1347-1363.
26. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
27. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244-13249.
28. Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1993, 98, 1358-1371.