Effects of substituents and solvents on the reactions of iminosphosphorane with formaldehyde: Ab initio MO calculation and Monte Carlo Simulation

Journal of Physical Chemistry A

Volumn 107, Issue 39, 2003, Pages 7945-7951

  Xue, Ying ^a   Kim, Chan Kyung ^a  

^a Inha University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZA-WITTIG REACTION; FREE ENERGY PERTURBATION; GAS PHASE CALCULATION; IMINOPHOSPHORANE; MOLECULAR ORBITAL METHOD; TETRAHYDROFURAN;

COMPOSITION EFFECTS; COMPUTER SIMULATION; ELECTRON ENERGY LEVELS; FORMALDEHYDE; METHANOL; MOLECULAR STRUCTURE; MONTE CARLO METHODS; PHASE TRANSITIONS; REACTION KINETICS; STEREOCHEMISTRY; THERMODYNAMIC PROPERTIES; WATER;

PHOSPHORUS COMPOUNDS;

EID: 0142135357     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp035398a     Document Type: Article

References (30)

1. Lischka, H. J. Am. Chem. Soc. 1977, 99, 353.
2. Holler, R.; Lischka, H. J. Am. Chem. Soc. 1980, 102, 4632.
3. Eades, R.A.; Gassman, P.G.; Dixon, D.A. J. Am. Chem. Soc. 1981, 103, 1066.
4. Vincent, M.A.; Schaefer, H.F., III; Schier, A.; Schmidbaur, H.J. J. Am. Chem. Soc. 1983, 105, 3806.
5. Dixon, D.A.; Smart, B.E. J. Am. Chem. Soc. 1986, 108, 7172.
6. Volatron, F.; Einstein, O. J. Am. Chem. Soc. 1987, 109, 1.
7. Nguyen, M.T.; Hegarty, A.F. J. Chem. Soc., Perkin Trans. 2 1987, 47.
8. Streitwieser, A.; Rajca, A.; McDowell, R.S.; Glaser, R.J. J. Am. Chem. Soc. 1987, 109, 4184.
9. Bachrach, S.M. J. Org. Chem. 1992, 57, 4367.
10. Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080.
11. Gololobov, Y.G.; Zhmurova, I.N.; Nasukhin, L.F. Tetrahedron 1981, 43, 437.
12. Mathis, R.; Zenati, N.; Ayed, N.; Sanchez, M. Spectrosc. Chim. Acta 1982, 38A, 1181.
13. Eric, F.V.S.; Kenneth, T. Chem. Rev. 1988, 88, 297.
14. Gololobov, Y.G.; Kasukhin, L.F. Tetrahedron 1992, 48, 1406.
15. Johnson, A.W. Ylides and Imines of Phosphorus; John Wiley & Sons: New York, 1993.
16. Gonbeau, D.; Pfister-Guillouzo, G.; Mazieres, M.-R.; Sanchez, M. Can. J. Chem. 1985, 63, 3242.
17. Sudhakar, V.; Lammertsma, K. J. Am. Chem. Soc. 1991, 113, 1899.
18. Koketsu, J.; Ninomiya, Y.; Suzuki, Y.; Koga, N. Inorg. Chem. 1997, 36, 694.
19. Lu, W.C.; Sun, Ch.Ch.; Zang, Q.J.; Liu, Ch. B. Chem. Phys. Lett. 1999, 311, 491.
20. Xue, Y.; Xie, D.; Yan, G. J. Phys. Chem. A 2002, 106, 9053.
21. Fukui, K. J. Phys. Chem. 1970, 74, 4161.
22. Breneman, C.M.; Wiberg, K.B. J. Comput. Chem. 1990, 11, 361.
23. 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.; 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 98, revision A.7; Gaussian Inc.; Pittsburgh, PA, 1998.
24. Jorgensen, W.L. Boss, version 4.2; Yale University: New Haven, CT.
25. Jorgensen, W.L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050.
26. Naito, T.; Nagase, S.; Yamataka, H. J. Am. Chem. Soc. 1994, 116, 10080.
27. Marcus, R.A. J. Chem. Phys. 1956, 24, 966.
28. Yoo, H.Y.; Houk, K.N. J. Am. Chem. Soc. 1997, 119, 2877.
29. Murdoch, J.R. J. Am. Chem. Soc. 1983, 105, 2660.
30. Murdoch, J.R. J. Am. Chem. Soc. 1983, 105, 2159.