IR structural identification of oxocumulene⋯HCl complexes generated in cryogenic matrixes. The product-like transition state of the corresponding electrophilic addition

Journal of Physical Chemistry A

Volumn 101, Issue 6, 1997, Pages 1093-1098

  Piétri, Nathalie ^a   Chiavassa, Thierry ^a   Allouche, Alain ^a   Aycard, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CALCULATIONS; CARBON; CHARACTERIZATION; ELECTRON ENERGY LEVELS; ELECTRON TRANSITIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; QUANTUM THEORY;

CRYOGENIC MATRIXES; ELECTROPHILIC ADDITION; MATRIX ISOLATION SPECTROSCOPY; OXOCUMULENE; PRODUCT LIKE TRANSITION STATE; QUANTUM CALCULATIONS;

ORGANIC COMPOUNDS;

EID: 0031555747     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp962953i     Document Type: Article

References (61)

1. (a) Sadlej, J.; Roos, B. O. Theor. Chim. Acta 1989, 73, 173.
2. (b) Bacskay, G. B. Mol. Phys. 1992, 77, 61.
3. (c) Mc Kellar, A. R. W.; Lu, Z. J. Mol. Spectrosc. 1993, 161, 542.
4. (d) De Almeida, W. B. Chem. Phys. Lett. 1990, 166, 589.
5. (e) Barnes, A. J. J. Mol. Struct. 1983, 100, 259.
6. (f) Barnes, A. J.; Lasson, E.; Nielsen, C. J. J. Chem. Soc., Faraday Trans. 1995, 91, 3111.
7. (g) Soper, P. D.; Legon, A. C.; Flygare, W. H. J. Chem. Phys. 1981, 74, 2138.
8. (h) Legon, A. C. Millen, D. J. Chem. Soc. Rev. 1992, 21, 71.
9. (i) Legon, A. C.; Chem. Sov. Rev. 1990, 19, 197.
10. (j) Legon, A. C.; Chem. Commun. 1996, 109.
11. (h) Fourati, N.; Silvi, B.; Perchard, J. P. J. Chem. Phys. 1984, 81, 4737.
12. (k) Altman, R. S.; Marshall, M. D.; Klemperer, W. J. Chem. Phys. 1982, 77, 4344.
13. (l) Zeegers-Huyskens, T. J. Mol. Struct. 1993, 297, 149.
14. (m) De Almeida, W. B.; Hinchiffe, A. Chem. Phys. 1989, 157, 143.
15. (n) Baiocchi, F. A.; Dixon, T. A.; Joyner, C. H.; Klemperer, W. J. Chem. Phys. 1981, 74, 654.
16. (o) Andrews, L.; Johnson, G. L. J. Chem. Phys. 1982, 76, 2875.
17. (p) Bach, S. B.; Ault, B. S. J. Phys. Chem. 1984, 88, 3600.
18. (q) Perchard, J. P.; Cipriani, J.; Silvi, B.; Maillard, D. J. Mol. Struct. 1982, 100, 317.
19. Schatte, G.; Willner, H.; Hoge, D.; Knözinger, E.; Schrems, O. J. Phys. Chem. 1989, 93, 6025.
20. (a) Lundell, J.; Räsänen, M. J. Phys. Chem. 1993, 97, 9657.
21. (b) Lundell, J.; Räsänen, M. J. Phys. Chem. 1995, 99, 14301.
22. (a) Kogure, N.; Ono, T.; Suzuki, E.; Watari, F. J. Mol. Struct. 1993, 296, 1.
23. (b) Kogure, N.; Hatakeyama, R.; Suzuki, E.; Watari, F. J. Mol. Struct. 1993, 299, 105.
24. (a) Monnier, M.; Allouche, A.; Verlaque, P.; Aycard, J. P. J. Phys. Chem. 1995, 99, 5977.
25. (b) Piétri, N.; Chiavassa, T.; Allouche, A.; Rajzman, M.; Aycard, J. P. J. Phys. Chem. 1996, 100, 7034.
26. Miller, F. A.; Fateley, W. G. Spectrochim. Acta 1964, 20, 253.
27. Monnier, M. Photoisomerisation et Photolyses en matrixes cryogeniques: identification des entités moléculaires et suivi cinétique par IR-TF. D.Sc. Thesis, Université de Provence, Marseille, 1991.
28. (a) Baxter, G. J.; Brown, R. F. C.; Eastwood, F. W.; Harrington, K. J. Tetrahedron Lett. 1975, 4283.
29. (b) Leung-Toung, R.; Wentup, C. J. Org. Chem. 1992, 57, 4850.
30. (c) Maĩer, G.; Heider, M.; Sierakowski, C. Tetrahedron Lett. 1991, 32, 4850.
31. Gaussian 94, Revision C.2; 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.; G. Zakrzewski, V.; 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.; and Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
32. (a) Hehre, W.J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
33. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
34. (c) Iordon, M. S. Chem. Phys. Lett. 1980, 76, 163.
35. (a) Tidwell, T. T. In Ketenes; John Wiley & Sons: New York, 1994; pp 4-32 and refences therein.
36. (b) Jorgensen, W. L.; Salem, L. In The Organic Chemist's Book of Orbitals; Academic Press: New York, 1973.
37. Boys, S.; Bernardi, F. Mol. Phys. 1970, 19, 553.
38. Herzberg, G. In Electronic Spectra of Polyatomic Molecules; Van Nostrand: Princeton, 1966.
39. (a) Del Bene, J. E. J. Am. Chem. Soc. 1972, 94, 3713.
40. (b) Mc Allister, M. A.; Tidwell, T. T. Can. J. Chem. 1994, 72, 882.
41. (a) Auwera, J. V.; Johns, J. V. C.; Poliansky, O. L. J. Chem. Phys. 1991, 95, 2299.
42. (b) Trinquier, G.; Malrieu, J. P. J. Am. Chem. Soc. 1987, 109, 5303.
43. (c) Durig, J. R.; Kalasinsky, V. F. J. Mol. Struct. 1978, 46, 1.
44. (d) Lozes, R. L.; Sabin, J. R.; Oddershede, J. J. Mol. Spectrosc. 1981, 86, 357.
45. (e) Duckett, J. A.; Mills, I. M.; Robiette, A. G. J. Mol. Spectrosc. 1976, 63, 249.
46. (a) Jensen, P. J. Mol. Spectrosc. 1984, 104, 59.
47. (b) Jensen, P.; Johns, J. W. L. J. Mol. Spectrosc. 1986, 106, 118.
48. Stout, J. M.; Dysktra, C. E. J. Am. Chem. Soc. 1995, 117, 5127.
49. Turro, N. J.; Hammond, W. B. J. Am. Chem. Soc. 1967, 89, 1028.
50. March, J. In Advanced Organic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1985.
51. Tortajada, J.; Provot, G.; Morizur, J. P.; Gal, J, F.; Maria, P. C.; Flammang, R.; Govaert, Y. Int. J. Mass. Spectrom. Ion Processes 1995, 141, 241.
52. Provot, G. In Complexes ion-neutre: espèces intermédiaires dans les décompositions de cations radicaux et cations organiques en phase gazeuse. Thesis, Université Pierre et Marie Curie, Paris, 1993.
53. (a) Cossu, M.; Bachmann, C.; N'Guessan, T. Y.; Viani, R.; Lapasset, J.; Aycard, J. P.; Bodot, H. J. Org. Chem. 1987, 52, 5313.
54. (b) Bürgi, H. B.; Dunitz, J. D.; Schefter, E. J. Am. Chem. Soc. 1973, 95, 5065.
55. (c) Bürgi, H. B.; Lehn, J. M.; Wipff, G. J. Am. Chem. Soc. 1974, 96, 1956.
56. (a) Lillford, P. J.; Satchell, D. P. N. J. Chem. Soc. B, 1968, 897.
57. (b) Satchell, D. P. N.; Satchell, R. S. Chem. Soc. Rev. 1975, 4, 231.
58. (c) See ref 19.
59. (a) Allen, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1987, 109, 2774.
60. (b) See ref 10a, p 623.
61. Allen, A. D.; McAllister, M. A.; Tidwell, T. T. J. Chem. Soc., Chem. Commun. 1995, 2547.