Quantum chemical model of an SN2 reaction in a microwave field

Journal of Physical Chemistry A

Volumn 106, Issue 37, 2002, Pages 8516-8524

  Kalhori, Shirzad ^a   Minaev, Boris ^b   Stone Elander, Sharon ^c   Elander, Nils ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^c KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; COMPLEXATION; COMPUTATIONAL METHODS; DISCRETE FOURIER TRANSFORMS; ELECTROMAGNETIC FIELDS; MICROWAVES; MOLECULAR VIBRATIONS; MOLECULES; PHOTONS; QUANTUM THEORY; RADIANT HEATING; SOLVENTS;

MICROWAVE FREQUENCIES; VIBRATIONAL MODES;

REACTION KINETICS;

EID: 0037136761     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp012643m     Document Type: Article

References (54)

1. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousel, J. Tetrahedron Lett. 1986, 27, 279.
2. Giguere, R.J.; Bray, T.L.; Duncan, S.M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945.
3. Abramovitch, R.A. Org. Prepr. Proced. Int. 1991, 23, 685.
4. Gedye, R.; Smith, F.; Westaway, K. J. Microwave Power Electromag. Energy 1991, 26, 1.
5. Bram, G.; Loupy, A.; Villemin, D. In Solid Supports and Catalysts in Organic Synthesis; Smith, K., Ed.; Ellis Horwood Ltd.: London, 1992; pp 302-326.
6. Majetich, G.; Hicks, R. Res. Chem. Intermed. 1994, 20, 61.
7. Strauss, C.R.; Trainor, R.W. Aust. J. Chem. 1995, 48, 1665.
8. Caddick, S. Tetrahedron 1995, 51, 10403.
9. Galema, S.A. Chem. Soc. Rev. 1997, 26, 233 and references therein.
10. Langa, F.; de la Cruz, P.; de la Hoz, A.; Diez-Ortiz, A.; Diez-Barra, E. Contemp. Org. Synth. 1997, 4, 373.
11. Kingston, H.M.; Haswell, S.J. Microwave-Enhanced Chemistry, Fundamentals, Sample Preparation and Applications; American Chemical Society: Washington, DC, 1997; and references therein.
12. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Math, D. Synth.-Stuttgart 1998, 9, 1213.
13. Gabriel, C.; Gabriel, S.; Grant, E.H.; Halstead, B.S.J.; Mingos, D.M.P. Chem. Soc. Rev. 1998, 27, 213 and references therein.
14. Strauss, C.R. Austr. J. Chem. 1999, 52, 83.
15. Varma, R.S. Green Chem. 1999, 1, 43.
16. Elander, N.; Jones, J.R.; Lu, S.-Y.; Stone-Elander, S. Chem. Soc. Rev. 2000, 29, 239.
17. Larhed, M.; Hallberg, A. Drug Discovery Today 2001, 6, 406-416.
18. Lidström, P.; Tiernye, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
19. Baghurst, D.R.; Mingos, D.M.P. J. Chem. Soc., Chem. Commun. 1992, 674.
20. Gedye, R.N.; Wei, J.B. Can. J. Chem. 1998, 76, 525.
21. Stuerga, D.A.C.; Gaillard, P. J. Microwave Power Electromagn. Energy 1996, 31, 87; J. Microwave Power Electromagn. Energy 1996, 31, 101.
22. Stuerga, D.A.C.; Gaillard, P. J. Microwave Power Electromagn. Energy 1996, 31, 87; J. Microwave Power Electromagn. Energy 1996, 31, 101.
23. Langa, F.; de la Cruz, P.; de la Hoz, A.; Espildora, E.; Cossio, F.P.; Lecea, B. J. Org. Chem. 2000, 65, 2499.
24. Langa, F.; de la Cruz, P.; de la Hoz, A.; Espildora, E.; Cossio, F.P.; Lecea, B. Proceedings of the International Conference on Microwave Chemistry. Antibes -Juan-les Pins; Inst. National Polytechn. de Toulouse: Toulouse, France, 2000.
25. Thorell, J.-O.; Stone-Elander, S.; Elander, N. J. Labeled Comp. Radiopharm. 1993, 31, 207.
26. Collin, R.E. Field theory of Guided Waves, 2nd ed; McGraw-Hill: New York, 1991. Collin, R.E. Foundations of Microwave Engineering, 2nd ed; McGraw-Hill: New York, 1992.
27. Collin, R.E. Field theory of Guided Waves, 2nd ed; McGraw-Hill: New York, 1991. Collin, R.E. Foundations of Microwave Engineering, 2nd ed; McGraw-Hill: New York, 1992.
28. Atkins, P.W. Molecular Quantum Mechanics; Clarendon Press: Oxford, U.K., 1983.
29. McQuarrie, D.A. Quantum chemistry; Oxford University Press: New York, 1983.
30. Debye, P., Ed.; Polar molecules; Dover: New York, 1945; p 147.
31. Buchner, R.; Batheland, J.; Stauber, J. Chem. Phys. Lett. 1999, 306, 57.
32. Modern Aspects of Microwave Spectroscopy; Chantry, G.W., Ed.; Academic Press: London 1979.
33. Parker, A.J. Chem. Rev. 1989, 69, 1.
34. Absubiojo, O.I.; Braumann, J.I. J. Am. Chem. Soc. 1979, 101, 3716.
35. Bergsma, J.P.; Gertner, B.J.; Wilson, K.R.; Hynes, J.T. J. Chem. Phys. 1987, 86, 1356.
36. Gertner, B.J.; Wilson, K.R.; Hynes, J.T. J. Chem. Phys. 1989, 90, 3537.
37. Amovilli, C.; Mennucci, B.; Floris, F.M. J. Chem. Phys. 1998, 102, 3023.
38. Han, C.-C.; Dodd, J.A.; Braumann, J.I. J. Phys. Chem. 1986, 90, 471.
39. Lyubartsev, A.P.; Laaksonen, A. J. Phys. Chem. 1996, 100, 16410.
40. Allen, M.P.; Tildsley, D.J. Computer Simulation of Liquids; Clarendon: Oxford, U.K., 1987.
41. Vande Linde, S.R.; Hase, W.L. J. Chem. Phys. 1990, 93, 7962.
42. Vande Linde, S.R.; Hase, W.L. J. Phys. Chem. 1990, 94, 2778.
43. 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; Gaussian, Inc.: Pittsburgh, PA, 1995.
44. Helgaker, T.; Jensen, H.J. Aa.; Jörgensen, P.; Olsen, J.; Ruud, K.; Ågren, H.; Andersen, T.; Bak, K.L.; Bakken, V.; Christiansen, O.; Dahle, P.; Dalskov, E.K.; Enevoldsen, T.; Fernandez, B.; Heiberg, H.; Hettema, H.; Jonsson, D.; Kirpekar, S.; Kobayashi, R.; Koch, H.; Mikkelsen, K.V.; Norman, P.; Packer, M.J.; Saue, T.; Taylor, P.R.; Vahtras, O. Dalton, An electronic structure program, release 1.0 (1997); see http://www.kjemi.uio.no/software/dalton/dalton.html.
45. N2 Mechanism; John Wiley & Sons, Inc.: New York, 1992.
46. Cossi, M.; Adamo, C.; Barone, V. Chem. Phys. Lett. 1998, 287, 1.
47. Larson, J.W.; McMhon, T.B. J. Am. Chem. Soc. 1985, 107, 766.
48. Albery, W.J.; Krevoy, M.M. Adv. Phys. Org. Chem. 1978, 16, 87.
49. Kalhori, S.; Elander, N.; Svennebrink, J.; Stone-Elander, S. Manuscript Department of Physics, Stockholm University, Stockholm, Sweden, 2001.
50. Jackson, J.D. Classical Electrodynamics, 3rd ed; John Wiley and Sons: New York, 1998.
51. Ensing, B.; Meijer, E.J.; Blöchl, P.E.; Baerends, E.J. J. Phys. Chem. A 2001, 105, 3300.
52. Mohamed, A.A.; Jensen, F. J. Phys. Chem. A 2001, 105, 3259.
53. Tucker, S.C.; Truhlar, D.G. J. Am. Chem. Soc. 1990, 112, 3347.
54. The Molden code is described at and can be obtained from: http://www.cmbi.kun.nl/̃ schaft/molden/molden.html.