Theoretical study of the structure - Property relationship in phosphole monomers

Journal of Organic Chemistry

Volumn 65, Issue 9, 2000, Pages 2631-2636

  Delaere, David ^a   Dransfeld, Alk ^a   Nguyen, Minh Tho ^a   Vanquickenborne, Luc G ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR STABILITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0034607681     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991373p     Document Type: Article

References (37)

1. (a) André, J. M.; Delhalle, J.; Brédas, J. L. Quantum Chemistry Aided Design of Organic Polymers; World Scientific: Singapore, 1991.
2. (b) Killian, J. G.; Coffey, B. M.; Gao, F.; Poehler, T. O.; Searson, P. C. J. Electrochem. Soc. 1996, 143, 936.
3. (a) Brédas, J. L.; Adant, C.; Tackx, P.; Persoons, A. Chem. Rev. 1994, 94, 243-278.
4. (b) Prasad, P.; Williams, D. Introduction to Nonlinear Optical Effects in Molecules and Polymers; John Wiley & Sons: New York, 1991.
5. (c) Okawa, H.; Wada, T.; Yamada, A.; Sasabe, H. Mater. Res. Soc. Symp. Proc. 1991, Vol. 214.
6. Jürimäe, T.; Strandberg, M.; Karelson, M.; Calais, J. L. Int. J. Quantum Chem. 1995, 54, 369.
7. Karelson, M.; Zerner M. C. Chem. Phys. Lett. 1994, 224, 213.
8. Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. Synth. Met. 1998, 96, 177.
9. Bevierre, M. O.; Mercier, F.; Ricard, L.; Mathey, F. Bull. Soc. Chim. Fr. 1992, 129, 1.
10. Mathey, F. J. Organomet. Chem. 1994, 475, 25.
11. Deschamps, E.; Ricard, L.; Mathey, F. Angew. Chem. 1994, 106, 11.
12. Holand, S.; Gandolfo, F.; Ricard, L.; Mathey, F. Bull. Soc. Chim. Fr. 1996, 133, 33.
13. (a) Prasad, N. P.; King, H. F.; Carlacci, L.; Chopra, P. J. Phys. Chem. 1989, 93, 7120.
14. (b) Brédas, J.-L. J. Chem. Phys. 1985, 82, 3808.
15. (c) Brédas, J.-L. Adv. Mater 1995, 7, 263.
16. (d) Ratner, M. A.; Marks, T. J.; Albert, I. D. L. J. Am. Chem. Soc. 1997, 119, 6575.
17. Bachrach, S. M. J. Org. Chem. 1993, 58, 5414.
18. Charrier, C.; Bonnard, H.; de Lauzon, G.; Mathey, F. J. Am. Chem. Soc. 1983, 105, 6871.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E., Jr.; 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.; 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, A. Nanayakkara, C. Y.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Reploglo, E. S.; Pople, J. A. Gaussian 98, Revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998.
21. 5h), that is, for the fully delocalized, highest symmetric systems. The empirical factor 225 provides an aromaticity scale in which JI = 0 for the Kekulé form of benzene (assuming 1.33 and 1.52 Å C-C lengths).
22. Julg, A.; François, P. Theor. Chim. Acta (Berl.) 1967, 7, 249.
23. Schleyer, P. v. R.; Freeman, P. K.; Jiao, H.; Goldfuss, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 337.
24. Dransfeld, A. Ph.D. Dissertation, Erlangen, Germany, 1998.
25. Mathey, F. Chem. Rev. 1988, 88, 429.
26. Keglevich, G.; Böcskei, Zs.; Keserü, G.; Ujszászi, K.; Quin, L. D. J. Am. Chem. Soc. 1997, 119, 5095.
27. Quin, L. D.; Keglevich, G.; Ionkin, A. S.; Kalgutkar, R.; Szalontai, G. J. Org. Chem. 1996, 61, 7808.
28. Nyulászi, L.; Soós, L.; Keglevich, G. J. Organomet. Chem. 1998, 566, 29.
29. Dransfeld, A.; Nyulászi, L.; Schleyer, P. v. R. Inorg. Chem. 1998, 37, 4413.
30. Nyulászi, L. J. Phys. Chem. 1995, 99, 586.
31. Normal pyramidality means similar to the pyramidality observed in the parent 1-H-1H-phosphole structure with ΣCPX = 293.3°.
32. Egan, W.; Tang, R.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 1442; 1971, 93, 6205.
33. Egan, W.; Tang, R.; Zon, G.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 1442; 1971, 93, 6205.
34. Dillon, K. B.; Mathey, F.; Nixon FRS, J. F. Phosphorus: The Carbon Copy; John Wiley & Sons: New York, 1998.
35. Bachrach, S. M.; Perriott, L. J. Org. Chem. 1994, 59, 3394.
36. Sunderlin, L. S.; Panu, D.; Puranik, D. B.; Ashe A. J.; Squires, R. R. Organometallics 1994, 13, 4732.
37. Quin, L. D.; McPhail, A. T.; Engel, J. F.; Coggon, P. J. Am. Chem. Soc. 1970, 92, 5779.