Phosphaalkenes with inverse electron density: Electrochemistry, electron paramagnetic resonance spectra, and density functional theory calculations of aminophosphaalkene derivatives

Journal of Physical Chemistry A

Volumn 107, Issue 24, 2003, Pages 4883-4892

  Rosa, Patrick ^a   Gouverd, Cyril ^a   Bernardinelli, Gérald ^b   Berclaz, Théo ^a   Geoffroy, Michel ^a  

^a Department of Physical Chemistry ^*  (Switzerland)

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER CONCENTRATION; CHEMICAL BONDS; CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTRONS; FREE RADICALS; NEGATIVE IONS; OXIDATION; PARAMAGNETIC RESONANCE; PHOSPHORUS; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL OXIDATION; ELECTRON DISTRIBUTION; PHOSPHAALKANES; PROTONATION;

PARAFFINS;

EID: 0037561555     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp030023a     Document Type: Article

References (71)

1. Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorous: the Carbon Copy; Wiley & Sons: Chichester, U.K., 1998.
2. Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: Stuttgart, 1990.
3. (a) Geoffroy, M.; Jouaiti, A.; Terron, G.; Cattani-Lorente, M.; Ellinger, Y. J. Phys. Chem. 1992, 96, 8241.
4. (b) Jouaiti, A.; Geoffroy, M.; Terron, G.; Bernardinelli, G. J. Am. Chem. Soc. 1995, 117, 2251.
5. (c) Al Badri, A.; Jouaiti, A.; Geoffroy, M. Magn. Reson. Chem. 1999, 37, 735.
6. (a) Fuchs, E.; Breit, B.; Heydt, H.; Schoeller, W.; Busch, T.; Kruger, C.; Betz, P.; Regitz, M. Chem. Ber. 1991, 124, 2843.
7. (b) Fuchs, E. P. O.; Heydt, H.; Regitz, M.; Schoeller, W. W.; Busch, T. Tetrahedron Lett. 1989, 20, 5111.
8. (a) Grobe, J.; Le Van, D.; Nientiedt, J.; Krebs, B.; Dartmann, M. Schem. Ber. 1988, 121, 655.
9. (b) Grobe, J.; Le Van, D.; Krebs, B.; Frölich, R.; Schiemann, A. J. Organomet. Chem. 1990, 389, C29-C33.
10. (c) Grobe, J.; Le Van, D.; Lange, G. Z. Naturforsch. B 1993, 48, 58.
11. Weber, L.; Uthmann, S.; Stamrnler, H.-G.; Neumann, B.; Schoeller, W. W.; Boese, R.; Blaser, D. Eur. J. Inorg. Chem. 1999, 2369.
12. Frison, G.; Sevin, A. J. Phys. Chem. A 1999, 103, 10998.
13. Frison, G.; Sevin, A. J. Organomet. Chem. 2002, 643-644, 105-11.
14. For a review about phosphaalkenes with inverse electron density: Weber, L. Eur. J. Inorg. Chem. 2000, 2425.
15. Arduengo, A. J., III; Carmalt, C. J.; Clybume, J. A. C.; Cowley, A. H.; Pyati, R. Chem. Commun. 1997, 981.
16. Schoeller, W. W.; Niemann, J.; Thiele, R.; Hang, W. Chem. Ber. 1991, 124, 417.
17. Oehme, H.; Leissring, E.; Meyer, H. Tetrahedron Lett. 1980, 21, 1141.
18. Oehme, H.; Leissring, E.; Meyer, H. Z. Chem. 1981, 21, 407.
19. Appel, R.; Knoll, F.; Ruppert, I. Angew. Chem., Int. Ed. Engl. 1981, 20, 731.
20. 3. Data were collected at 200 K on a Stoe IPDS diffractometer. R = 0.039, ωR = 0.038, S = 1.26(2) for 2526 contributing reflections and 274 variables. Additional details are given as Supporting Information.
21. Schmidpeter, A.; Zirzow, K.-H.; Willhalm, A.; Holmes, J. M.; Day, R. O.; Holmes, R. R. Angew. Chem., Ind. Ed. Engl. 1986, 25, 457
22. Schmidpeter, A.; Zirzow, K.-H.; Willhalm, A.; Holmes, J. M.; Day, R. O.; Holmes, R. R. Angew. Chem., Ind. Ed. Engl. 1986, 25, 457.
23. Weber, L.; Uthmann, S.; Stammler, H.-G.; Neumann, B.; Schoeller, W. W.; Boese, R.; Bläser, D. Eur. J. Inorg. Chem. 1999, 1369.
24. Navech, J.; Majoral, J. P.; Kraemer, R. Tetrahedron Lett. 1983, 52, 5885.
25. Navech, J.; Revel, M.; Kraemer, R. Phosphorus Sulfur 1984, 21, 105.
26. In contrast to refs 19 and 20, 2 was not found to be an oil, but a crystalline compound (mp = 80 °C).
27. Soulié, E.; Berclaz, T.; Geoffroy, M. In AIP Conference Proceedings 330; Bemardi, F., Rivail, J.-L., Eds.
28. Soulié, E.; Berclaz, T.; Geoffroy, M. Computers and Chemistry; 1996; p 627.
29. WinEPR Simfonia, vJ.25, Bruker Analytische Messtecknik Gmbh, 1996.
30. 2 has been rotated by 90°. Schmidt, M. W.; Truong, P. N.; Gordon, M. S. J. Am. Chem. Soc. 1987, 109, 5217.
31. Arduengo, A. J., III; Rasika Dias, H. V.; Calabrese, J. C. Chem. Lett. 1997, 143-44.
32. Arduengo, A. J., III; Calabrese, J. C.; Cowley, A. H.; Rasika Dias, H. V.; Goerlich, J. R.; Marshall, W. J.; Riegel, R. Inorg. Chem. 1997, 36, 2151.
33. Joantéguy, S.; Pfister-Guillouso, G.; Chermette, H. J. Phys. Chem. A 1999, 103, 350.
34. Ohno, K.; Okamura, K.; Yamakado, H.; Hoshino, S.; Takami, T.; Yamauchi, M. J. Phys. Chem. 1995, 99, 14247.
35. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref Data 1988, 17 (Suppl. No. 1).
36. Lacombe, S.; Gonbeau, D.; Cabioch, J.-L.; Pellerin, B.; Denis, J.-M.; Pfister-Guillouzo, G. J. Am. Chem. Soc. 1998, 110, 6964.
37. Voyna, V. I.; Alekseiko, L. N.; Okhota, B. V.; Ruban, A. V.; Romanenko, V. D.; Markovskii, L. N. J. Gen. Chem. USSR (Engl. Trans.) 1991. 61, 463.
38. Chernega, A. N.; Antipin, M. Y.; Struchkov, Y. T.; Sarina, T. V. Romanenko, V. D. J. Struct. Chem. 1986, 27, 741.
39. Nguyen, M. T.; Creve, S.; Eriksson, L. A.; Vanquickenbome, L. G. Mol. Phys. 1997, 91, 537.
40. Sidorenkova, H. Ph.D. Thesis, University of Geneva, Switzerland. 2001.
41. Cramer, C. J.; Lim, M. H. J. Phys. Chem. 1994, 98, 5024.
42. Kutzelnigg, W.; Fleischer, U.; Schindler, M. NMR-Basic Principles and Progress; Springer-Verlag: Heidelberg, 1991; Vol. 23, p 167.
43. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
44. Glendening E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Natural Bond Orbital Analysis, NBO 3.1; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI. Calculations performed at the B3LYP/6-31+G(d) level.
45. (a) Chentit, M.; Sidorenkova, H.; Jouaiti, A.; Terron, G.; Geoffroy, M.; Ellinger, Y. J Chem. Soc., Perkin Trans. 2 1997, 921.
46. (b) Alberti, A.; Benaglia, M.; D'Angelantonio, M.; Emmi, S. S.; Guerra, M.; Hudson, A.; Macciantelli, D.; Paolucci, F.; Roffia, S. J Chem. Soc., Perkin Trans. 2 1999, 309.
47. From a comparison with atomic coupling constants reported in: Morton, J. R.; Preston, K. F. J. Magn. Reson. 1978, 30, 577.
48. (a) Cetinkaya, B.; Hudson, A.; Lappert, M. F.; Goldwhite, H. J. Chem. Soc., Chem. Commun. 1982, 609.
49. (b) Geoffroy, M.; Lucken, E. A. C.; Mazeline, C. Mol. Phys. 1974, 28, 839.
50. (c) Kajita, M.; Endo, Y.; Hirota, E. J. Mol. Spectr. 1987, 124, 66.
51. (d) Bonnazzola, L.; Michaut, J. P.; Roncin, J. J. Chem. Phys. 1981, 75, 4829.
52. (e) Nelson, W.; Jackel, G.; Gordy, W. J. Chem. Phys. 1970, 52, 4572.
53. (f) Fullam, B. W.; Mishra, S. P.; Symons, M. C. R. J. Chem. Soc., Dalton Trans., 1974, 2145.
54. (g) Berclaz, T.; Geoffroy, M. Helv. Chim. Acta 1978, 61, 684.
55. •+) is given as Supporting Information.
56. 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.; 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, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
57. Becke, A. D. J Chem. Phys. 1993, 98, 5648.
58. Lee, C.; Yang, W.; Parr; R. G. Phys. Rev. B, 1988, 37, 785.
59. Wong, M. W. Chem. Phys. Lett. 1996, 256, 391.
60. Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
61. P. F. Flukiger, Development of the molecular graphics package MOLEKEL and its application to selected problems in organic and organometallic chemistry, Thèse No. 2561, Département de chimie physique, Université de Genève, Genève, 1992.
62. Portmann, S.; Luthi, H. P. Chimia 2000, 54, 766.
63. Widauer, C.; Shiahuy Chen, G.; Grützmacher, H. Chem. Eur. J. 1998, 4, 1154.
64. DeFrees, D. J.; McLean, A. D. J. Comput. Chem. 1986, 3, 321.
65. Barone, V. In Recent Advances in Dentistry Functional Methods, Part I; Chong, D. P., Ed.; World Scientific Publishing Co.: Singapore, 1996.
66. Rega, N.; Cossi, M.; Barone, V. J. Chem. Phys. 1996, 105, 11060.
67. Barone, V. Chem. Phys. Lett. 1996, 262, 201.
68. Yoshifuji, M.; Toyota, K.; Shibayama, K.; Inamoto. N. Chem. Lett. 1983, 1653.
69. Cowley, A. H.; Kilduff, J. E.; Newman, T. H.; Pakulski, M. J. Am. Chem. Soc. 1982, 104, 5820.
70. Meerwein, H.; Florian, W.; Schön, N.; Stopp, G. J. Liebigs Ann. Chem. 1961, 641, 1.
71. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169.