Theoretical prediction of benzyne-like species in pyrene diradicals

Journal of Physical Chemistry A

Volumn 108, Issue 23, 2004, Pages 5111-5116

  Garcia Cruz I ^a   Martinez Magadan J M ^a   Bofill, J M ^b   Illas, F ^a,b  

^a INSTITUTO MEXICANO DEL PETRÓLEO   (Mexico)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; DEHYDROGENATION; ELECTRONIC STRUCTURE; FREE RADICALS; GROUND STATE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PERTURBATION TECHNIQUES; REACTION KINETICS; WAVE EQUATIONS;

DIRADICAL FORMATION; ELECTRON AFFINITIES; MULTICONFIGURATIONAL WAVE FUNCTIONS; SINGLET-TRIPLET SPLITTING;

AROMATIC COMPOUNDS;

EID: 17044454917     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp037795r     Document Type: Article

References (61)

1. New Trends in Coal Science; NATO ASI Series, Series C: Mathematical and Physical Sciences; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1988; Vol. 244.
2. Polycyclic Aromatic Hydrocarbons: Evaluation of Sources and Effects, Committee on Pyrene and Selected Analogues; Board on Toxicology and Environmental Health Hazards, The National Academies Press: Washington, DC, 1983.
3. Blakeslee, J. R.; Elliot, A. M.; Carter, L. J. Polycydic Aromatic Hydrocarbon: Formation, Metabolism and Measurement, Cooke, M., Dennis, A. J., Eds.; 1983; pp 123-134.
4. Ritcher, H.; Benish, T. G.; Mazyar, O. A.; Green, W. H.; Howard, J. B. Proc. Combust. Inst. 2000, 28, 2609.
5. Ruiz-Morales, Y. J. Phys. Chem. A 2002, 106, 11283.
6. García-Cruz, I.; Martínez-Magadán, J. M.; Guadarrama, P.; Salcedo, R.; Illas, F. J. Phys. Chem. A 2003, 107, 1597.
7. Groenzin, H.; Mullins, O. C. Energy Fuels 2000, 14, 677.
8. Murgich, J.; Abanero, J. A. Energy Fuels 1998, 12, 239.
9. Sander, W. Acc. Chem. Res. 1999, 32, 669.
10. Hoffmann, R. W. Dehydrobenzene and Cycloalkenes; Academic Press: New York, 1967.
11. Isaac,N. S. Reactive Intermediates in Organic Chemistry; Wiley: London, 1975.
12. Levin, R. H. Reactive Intermediates; Jones, M., Moss, R. A., Eds.; Wiley: New York, 1985; Vol. 1, pp 1-18.
13. Gilchrist,T. L. Carbenes, Nitrenes, and Arynes; Appleton-Centrury-Croft: New York, 1969.
14. Roberts, J. D.; Semenow, D. A.; Simmons, H. E., Jr.; Carlsmith, L. A. J. Am. Chem. Soc. 1956, 78, 601.
15. Winkler, K.; Sander, W. J. Phys. Chem. A 2001, 105, 10422.
16. Marquardt, R.; Sander, W.; Kraka, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 746.
17. Kraka, E.; Anglada, J.; Hjerpe, A.; Filatov, M.; Cremer, D. Chem. Phys. Lett. 2001, 348, 115-125.
18. Sander, W.; Exner, M.; Winkler, M.; Balster, A.; Hjerpe, A.; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 2002, 124, 13072-13079.
19. Marquardt, R.; Balater, A.; Sander, W.; Kraka, E.; Cremer, D.; Radziszewski, J. G. Angew. Chem., Int. Ed. Engl. 1998, 37, 955.
20. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J. Am. Chem. Soc. 1998, 120, 5279.
21. Kukolich, S. G.; McCarthy, M. C.; Thaddeus, P. J. Phys. Chem. A 2004, 108, 2645.
22. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
23. Kawai, K.; Takada, K.; Tojo, S.; Ichinose, N.; Majima, T. J. Am. Chem. Soc. 2001, 123, 12688.
24. Kawai, K.; Myamoto, K.; Tojo, S.; Majima, T. J. Am. Chem. Soc. 2003, 125, 912.
25. Cui, G.; Simmerling, C. J. J. Am. Chem. Soc. 2002, 124, 12154.
26. Salama, F.; Allamandola, L. J. Nature (London) 1992, 358, 42.
27. Szczepanski, J.; Vala, M. Nature (London) 1993, 363, 699.
28. Scotti, R.; Montanari, L. Asphaltenes, Fundamentals and Applications; Sheu, E. Y., Mullins, O., Eds.; Plenum Press: New York, 2001.
29. Heaney, H. Chem. Rev. 1962, 62, 81.
30. Maruani, J.; Kite, T. M.; Korb, J. P.; Gille, X. Mol. Phys. 1978, 36, 1261.
31. Berk, N. F.; Bizzarro, W.; Rosenthal, J.; Yarmus, L. Phys. Rev. B 1981, 23, 5661.
32. de Graaf, C.; Sousa, C.; Moreira, I. de P. R.; Illas, F. J. Phys. Chem. A 2001, 105, 11371.
33. Slipchenko, L. V.; Krylov, A. I. J. Chem. Phys. 2002, 117, 4694.
34. Shao, Y.; Head-Gordon, M.; Krylov, A. I. J. Chem. Phys. 2003, 118, 4807.
35. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. A 1988, 38, 3098.
37. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
38. Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
39. Barone, V.; di Matteo, A.; Mele, F.; Moreira, I. de P. R.; Illas, F. Chem. Phys. Lett. 1999, 302, 240.
40. Barone, V.; Beneini, A.; Ciofini, I.; Daul, C. J. Phys. Chem. A 1999, 103, 4875.
41. Caballoll, R.; Castell, O.; Illas, F.; Malrieu, J. P.; Moreira, I. de P. R. J. Phys. Chem. A 1997, 101, 7860.
42. Cramer, C. J.; Nash, J. J.; Squires, R. R. Chem. Phys. Lett. 1997, 277, 311.
43. Grafenstein, J.; Kraka, E.; Filatov, M.; Cremer, D. Int. J. Mol. Sci. 2002, 3, 360.
44. Cremer, D.; Filatov, M.; Polo, V.; Kraka, E.; Shaik, S. Int. J. Mol. Sci. 2002, 3, 604.
45. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. J. Phys. Chem. 1990, 94, 5483.
46. Andersson, K.; Malmqvist, P.-Å.; Roos, B. O. J. Chem. Phys. 1992, 96, 1218.
47. Widmark, P. O.; Persson, B. J.; Roos, B. O. Theor. Chin. Acta 1990, 77, 291.
48. Schleyer, P. v. R.; Maerker, C.; Dransfield, A.; Jia, H.; Eikema-Hommes, N. J. R. v. J. Am. Chem. Soc. 1996, 118, 6317.
49. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1993, 210, 223.
50. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
51. Havenith, R. W. A.; Jiao, H.; Jenneskens, L. W.; Lenthe, J. H. v.; Sarobe, M.; Schleyer, P. v. R.; Kataoka, M.; Necula, A.; Scott, L. T. J. Am. Chem. Soc. 2002, 124, 2362.
52. Havenith, R. W. A.; Lenthe, J. H. v.; Dijkstra, F.; Jenneskens, L. W. J. Phys. Chem. A 2001, 105, 3838.
53. Steiner, E.; Fowler, P. W.; Jenneskens, L. W.; Havenith, R. W. A. Eur. J. Org. Chem. 2002, 163.
54. Frisch, M. J.; et al. Gaussian 98 Revision A.7; Gaussian, Inc.; Pittsburgh, PA, 1998.
55. Andersson, K.; Barysz, M.; Bernhardsson, A.; Blomberg, M. R. A.; Carissan, Y.; Cooper, D. L.; Fülscher, M. P.; Gagliardi, L.; de Graaf, C.; Hess, B. A.; Karlström, G.; Lindh, R.; Malmqvist, P.-Å.; Nakajima, T.; Neogrády, P.; Olsen, J.; Roos, B. O.; Schimmelpfennig, B.; Schütz, M.;. Seijo, L; Serrano-Andrés, L.; Siegbahn, P. E. M.; Stålring, J.; Thorsteinsson, T.; Veryazov, V.; Widmark, P.-O. MOLCAS Version 5.4. Lund University: Lund, Sweden, 2002.
56. Herbstein, F. H.; Marsh, R. E.; Samson, S. Acta Crystallogr., B 1994, 50, 174.
57. Illas, F.; Moreira, I. de P. R.; de Graaf, C.; Barone, V. Theor. Chem. Acc. 2000, 104, 265.
58. Salem, L.; Rowland, C. Angew. Chem., Int. Ed. Engl. 1972, 11, 92.
59. Grafenstein, J.; Hjerpe, A. M.; Kraka, E.; Cremer, D. J. Phys. Chem. A 2000, 104, 1748.
60. Grafenstein, J.; Cremer, D. Mol. Phys. 2001, 99, 981.
61. Blanksby, S. J.; Ellison, C. B. Acc. Chem. Res. 2003, 36, 255.