Stability, metastability, and unstability of three-electron-bonded radical anions. A model ab initio theoretical study

Journal of the American Chemical Society

Volumn 124, Issue 39, 2002, Pages 11781-11790

  Braïda, Benoît ^a   Thogersen, Lea ^a   Wu, Wei ^b   Hiberty, Philippe C ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION ENERGY;

CHEMICAL BONDS; DISSOCIATION; ENERGY GAP; STABILITY;

NEGATIVE IONS;

ALKYL GROUP; ANION; FLUORINE DERIVATIVE; RADICAL;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; DISSOCIATION; ELECTRON; ENERGY; MOLECULAR MODEL; MOLECULAR STABILITY;

EID: 0037009965     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026707y     Document Type: Article

References (92)

1. For leading references, see: Asmus, K. D. Acc. Chem. Res. 1979; 12, 436.
2. (b) Göbl, M.; Bonifacic, M.; Asmus, K. D. J. Am. Chem. Soc. 1984, 106, 5984.
3. (c) Asmus, K. D. Nukleonika 2000, 45, 3 and references therein.
4. (a) Asmus, K.-D. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Amus K.-D., Eds.; Plenum Press: New York and London, 1990; p 155.;
5. (b) Glass, R. S. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Amus K.-D., Eds.; Plenum Press: New York and London, 1990; p 213.
6. (c) Gilbert, B. C. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Amus K.-D., Eds.; Plenum Press: New York and London, 1990; p 135.
7. Scaiano, J. C.; Garcia, S.; García, H. Tetrahedron Lett. 1997, 38, 5929.
8. Lakkaraju, P. S.; Shen, K.; Roth, H. D.; García, H. J. Phys. Chem. A 1999, 103, 7381.
9. (a) Ortiz de Montellano, P. R. O. Acc. Chem. Res. 1987, 20, 289.
10. (b) Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996; 96, 2841 and references therein.
11. (a) Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem.-Eur. J. 1998, 4, 193.
12. (b) Ogliaro, F.; Harris, N.; Cohen, S.; Filatov, M.; De Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2000, 122, 8977 and references therein.
13. Steffen, L. K.; Glass, R. S.; Sabahi, M.; Wilson, G. S.; Schöneich, C.; Mahling, S.; Asmus, K. D. J. Am. Chem. Soc. 1991, 113, 2141.
14. Abu-Raqabah, A.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1990, 86, 3293 and refs 4-7 therein.
15. Abu-Raqabah, A.; Symons, M. C. R. J. Am. Chem. Soc. 1990, 112, 8614.
16. Champagne, M. H.; Mullins, M. W.; Colson, A. O.; Sevilla, M. D. J. Phys, Chem. 1991, 95. 6487.
17. (a) Janssen, R. A. J.; Aagaard, O. M.; Van der Woerd, M. J.; Buck, H. M. Chem. Phys. Lett. 1990, 171, 127.
18. (b) Aagaard, O. M.; De Waal, B. F. M.; Cabbolet, M. J. T. F.; Janssen, R. A. J. J. Phys. Chem. 1992, 96, 614.
19. Chateauneuf, J. E. Chem. Commun. 1998, 2099.
20. Wang, W.; Schuchmann, M. N.; Schuchmann, H. P.; Knolle, W.; Von Sonntag, J.; Von Sonntag, C. J. Am. Chem. Soc. 1999, 121, 238.
21. El Hanine Lmoumène, C.; Conte, D.; Jacquot, J.-P.; Houée-Levin, C. Biochemistry 2000, 39, 9295.
22. Abu-Raqabah, A.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1990, 86, 3293 and refs 4-7 therein.
23. Raynor, J. B.; Rowland, I. J.; Symons, M. C. R. J. Chem. Soc., Faraday Trans. 1991, 87, 571.
24. (a) Bowman, R. J.; Symons, M. C. R. J. Chem. Soc., Perkin Trans. 2 1990, 975.
25. (b) Shanker Rai, U.; Symons, M. C. R.; Wyatt, J. L.; Bowman, R. J. Chem. Soc., Faraday Trans. 1993, 89, 1199.
26. (a) Marignier, J.-L.; Belloni, J. J. Phys. Chem. 1981, 85, 3100.
27. (b) Belloni, J.; Marignier, J.-L.; Katsumura, Y.; Tabata, Y. J Phys. Chem. 1986, 90, 4014.
28. (c) Belloni, J.; Marignier, J.-L. Radiat. Phys. Chem. 1989, 34, 157.
29. (d) Gauduel, Y.; Pommeret, S.; Antonetti, A.; Belloni, J.; Marignier, J.-L. J. Phys. 1991, 1, 161.
30. (a) Berges, J.; Kassab, E.; Adjadj, E. Houée-Levin, C. J. Phys. Chem. 1997, 101, 7809.
31. (b) Berges, J.; Fuster, F.; Jacquot, J.-P.; Silvi, B.; Houée-Levin, C. Nukleonika 2000, 45, 2329.
32. Gauduel, Y.; Marignier, J.-L.; Belloni, J.; Gelabert, H. J. Phys. Chem. A 1997, 101, 8979.
33. See the compilation of experimental bonding energies in Gilbert, T. L.; Wahl, A. C. J. Chem. Phys. 1971, 55, 5247.
34. Huber, K. P.; Herzberg, G. Molecular Spectra and Molecular Structure IV. Constants of Diatomic Molecules; Van Nostrand Reinhold: New York, 1979.
35. Dehmer, P. H.; Pratt, S. T. In Photophysics and Photochemistry in the Vacuum Ultraviolet; McGlynn, S. P., Findley, G. L., Hueber, R. H., Eds.; D. Reidel Publishing Co.: Dordrecht, The Netherlands, 1985; p 260.
36. Clark, T. J. Am. Chem. Soc. 1988, 110, 1672-1678
37. Gill P. M. W.; Radom L. J. Am. Chem. Soc. 1988, 110, 4931-4941
38. (a) Chen, E. C. M.; Wentworth, W. E. J. Phys. Chem. 1985, 89, 4099.
39. (b) Dojahn, J. G.; Chen, E. C. M.; Wentworth, W. E. J. Phys. Chem. 1996, 100, 9649
40. (a) Bowmaker, G. A.; Schmerdtfeger, P.; Von Szentpály, L. J. Mol. Struct.: THEOCHEM 1989, 87.
41. (b) Wenthold, P. G.; Squires, R. R. J. Phys. Chem. 1995, 99, 2002.
42. Braïda, B.; Hiberty, P. C. J. Phys. Chem. A 2000, 104, 4618-4628
43. Naito, A.; Akasaka, K.; Hatano, H. J. Magn. Reson. 1976, 24, 53.
44. Bonnazola, L.; Michaut, J. P.; Roncin, J. J. Chem. Phys. 1985, 83, 2727.
45. Colaneri, M. J.; Box, H. C. J. Chem. Phys. 1986, 84, 2926.
46. Franzi, R.; Geoffroy, M.; Reddy, M. V. V. S.; Weber, J. J. Phys. Chem. 1987, 91, 3187.
47. (a) Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1986, 90, 5915.
48. (b) Surdhar, P. S.; Armstrong, D. A. J. Phys. Chem. 1987, 91, 6532.
49. Zhu, J.; Petit, K.; Colson, A. O.; DeBolt, S.; Sevilla, M. D. J. Phys. Chem. 1991, 95, 3676.
50. Benassi, R.; Taddei, F. J. Phys. Chem. A 1998, 102, 6173
51. Mezyk, S. P. Chem. Phys. Lett. 1995, 235, 89.
52. Karmann, W.; Meissner, G.; Henglein, A. Z. Naturforsch. 1967, B22, 273.
53. Karmann. W.; Granzow, A.; Meissner, G.; Henglein, A. Int. J. Radiat. Phys. Chem. 1969, 1. 395.
54. Lin, M. J.; Lunsford, J. H. J. Phys. Chem. 1976, 80, 2015.
55. Benassi, R.; Fiandri, G. L.; Taddei, F. Tetrahedron 1994, 43, 12469.
56. (a) Schöneich, C.; Aced, A.; Asmus, K. D. J. Am. Chem. Soc. 1991, 113, 375.
57. (b) Schöneich, C.; Aced, A.; Asmus, K. D. J. Am. Chem. Soc. 1993, 115. 11376.
58. (c) Schöneich, C.; Bobrowski, K. J. Phys. Chem. 1994, 98, 12613.
59. (d) Kishore, K.; Anklam, E.; Aced, A.; Asmus, K.-D. J. Phys. Chem. A 2000, 104, 9646.
60. Dézarnaud-Dandine, C.; Sevin. A. J. Am. Chem. Soc. 1996, 118, 4427.
61. Sommerfeld, T. Phys. Chem. Chem. Phys. 2001, 3, 2394.
62. Schroder D.; Schalley C. A.; Goldberg N.; Hrusak J.; Schwarz H. Chem.Eur. J. 1996, 2, 1235.
63. van Doren, J. M.; Barlow, S. E.; DePuy, C. H.; Bierbaum, V. J. Am. Chem. Soc. 1987, 109, 4412.
64. Humbel, S.; Demachy, I.; Hiberty, P. C. Chem. Phys. Lett. 1995, 247, 126.
65. Hrusak, J.; Friedrichs, H.; Schwarz, H.; Razafinjanahary, H.; Chermette, H. J. Phys. Chem. 1996, 100, 100.
66. Skurski, P.; Gutowski, M.; Simons, J. J. Chem. Phys. 1999, 110, 274.
67. Skurski, P.; Gutowski, M.; Simons, J. J. Phys. Chem. A 1999, 103, 625.
68. Tada, T.; Yoshimura, R. J. Phys. Chem. A 1993, 97, 1019.
69. Fourré, L.; Silvi, B.; Sevin, A.; Chevreau, H. J. Phys. Chem. A 2002, 106, 2561.
70. (a) Noodleman, L.; Post, D., Baerends, E. J. J. Phys. Chem. 1982, 64, 159.
71. (b) Braïda, B.; Hiberty, P. C.; Savin. A. J. Phys. Chem. A 1998, 102, 7872.
72. (c) Sodupe, M.; Bertran, J.; Rodriguez-Santiago, L.; Baerends, E. J. J. Phys. Chem. A 1999, 103, 166.
73. (d) Chermette, H.; Ciofini, I.; Mariotti, F.; Daul, C. J. Chem. Phys. 2001, 115, 11068.
74. (a) Merkle, F.; Savin, A.; Preuss, H. J. Chem. Phys. 1992, 97, 9216.
75. (b) Bally, T.; Sastry, G. N. J. Phys. Chem. A 1997, 101, 7923.
76. (c) Zhang, Y.; Yang, W. J. Chem. Phys. 1998, 109, 2604.
77. (d) Chermette, H.; Ciofini, I., Mariotti, F.; Daul, J. Chem. Phys. 2001, 114, 1447.
78. Hiberty, P. C.; Humbel, S.; Danovich, D.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 9003.
79. Braïda, B.; Lauvergnat, D.; Hiberty, P. C. J. Chem. Phys. 2001, 115, 90.
80. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
81. (b) Kendall, R. A.; Dunning, T. H., Jr.; Harrison, J. J. Chem. Phys. 1992, 96, 6769.
82. (c) Woon, D. E.; Dunning, T. H. J. Chem. Phys. 1993, 98, 1358.
83. CRC Handbook of Chemistry and Physics, 70th ed.; CRC Press: Boca Raton, FL, 1989-1990; p E-67.
84. (a) Hiberty, P. C.; Flament, J. P.; Noizet, E. Chem. Phys. Lett. 1992, 189, 259.
85. (b) Hiberty, P. C.; Humbel, S.; Byrman, C. P.; van Lenthe, J. H. J. Chem. Phys. 1994, 101, 5969.
86. (c) Hiberty, P. C.; Humbel, Archirel, P. J. Phys. Chem. 1994, 98, 11697.
87. (d) Hiberty, P. C. In Modern Electronic Structure Theory and Applications in Organic Chemistry; Davidson, E. R., Ed.; World Scientific: River Edge, NY, 1997; pp 289-367.
88. 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.; Butant, 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, R.; 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. Guassian 98 (revision A.6); Gaussian, Inc.: Pittsburgh, PA, 1998.
89. MOLPRO is a package of ab initio programs written by H.-J. Werner and P. J. Knowles, with contributions from R. D. Amos, A. Bernhardsson, A. Berning, P. Celani, D. L. Cooper, M. J. O. Deegan, A. J. Dobbyn, F. Eckert, C. Hampel, G. Hetzer, T. Korona, R. Lindh, A. W. Lloyd, S. J. McNicholas, F. R. Manby, W. Meyer, M. E. Mura, A. Nicklass, P. Palmieri, R. Pitzer, G. Rauhut, M. Schütz, H. Stoll, A. J. Stone, R. Tarroni, and T. Thorsteinsson.
90. Wu, W.; Song, L.; Mo, Y.; Zhang, Q. XIAMEN99-An ab initio Spin-Free Valence Bond Program; Xiamen University: Fujian, People's Repulic of China, 1999.
91. Braïda, B.; Hazebroucq, S.; Hiberty, P. C. J. Am. Chem. Soc. 2002, 124, 2371.
92. The Hartree-Fock and VB descriptions of three-electron bonds are equivalent only in the minimal basis set. i.e., if no orbital optimization is performed (see ref 54).