Rotational Barriers, Charges, and Spin Densities in Alkyl Aryl Sulfide Radical Cations: A Density Functional Study

Journal of Physical Chemistry A

Volumn 108, Issue 12, 2004, Pages 2332-2338

  Baciocchi, Enrico ^a   Gerini, Maria Francesca ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; ELECTRIC CHARGE; FREE RADICALS; IONIZATION; MOLECULAR STRUCTURE; OXIDATION; PROBABILITY DENSITY FUNCTION; SULFUR COMPOUNDS;

ELECTRON ACCEPTORS; ELECTRON DONORS; ENERGY BARRIERS;

AROMATIC COMPOUNDS;

EID: 1842737651     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0367124     Document Type: Article

References (31)

1. Dewar, P. S.; Ernstbrunner, E.; Gilmore, J. R.; Godfrey, M.; Mellor, J. M. Tetrahedron 1974, 30, 2455-2459.
2. Glass, R. S.; Broeker, J. L.; Jatcko, M. E. Tetrahedron 1989, 45, 1263-1272.
3. Dolgounitcheva, O.; Zakrzewski, V. G.; Ortiz, J. V.; Ratovski, G. V. Int. J. Quantum Chem. 1998, 70, 1037-1043.
4. Dal Colle, M.; Distefano, G.; Jones, D.; Modelli, A. J. Phys. Chem. A 2000, 104, 8227-8235.
5. Alberti, A.; Pedulli, G. F.; Tiecco, M.; Testaferri, L.; Tingoli, M. J. Chem. Soc., Perkin Trans. 2 1984, 975-979.
6. Skotheim, T. A. Handbook of Conducting Polymers; Marcel Dekker: New York, 1986.
7. Chatgilialoglu, C., Asmus, K.-D. Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Plenum Press: New York, 1990.
8. Korzeniowska-Sobczuk, A.; Hug, G. L.; Carmichael, I.; Bobrowski, K. J. Phys. Chem. A 2002, 106, 9251-9260.
9. Bally, T.; Borden, W. T. Rev. Comput. Chem. 1999, 13, 1-97.
10. 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.
11. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
12. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
13. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; J. Wiley & Sons: New York, 1987.
14. Curtiss, L. A.; Raghavachari, K.; Redfern, P. C.; Pople J. A. J. Chem. Phys. 1997, 106, 1063-1079.
15. Arulmozhiraja, S.; Sato, T.; Yabe, A. J. Comput. Chem. 2001, 22, 923-930.
16. Kraka, E.; Cremer D. J. Comput. Chem. 2001, 22, 216-220.
17. Johnson, W. T. G.; Cramer C. J. J. Am. Chem. Soc. 2001, 123, 923-928.
18. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129-145.
19. Besler, B. H.; Merz, K. M. Jr.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431-439.
20. 4SMe was studied for 0° ≤ φ ≤ 180°, and it was found that the cis and trans isomers have a similar energy.
21. 8 using a smaller basis set.
22. .+ was studied for 0° ≤ φ ≤ 180̈, and it was found that the trans isomer has an energy a little lower than that of the cis isomer.
23. Matsumura, Y.; Yamada, M. Tetrahedron 1995, 23, 6411-6418.
24. Vondràk, T.; Sato, S.; Spirko, V.; Kimura, K. J. Phys. Chem. A 1997, 101, 8631-8638.
25. Frey, J. E.; Aiello, T.; Beaman, D. N.; Hutson, H.; Lang, S. R.; Puckett, J. J. J. Org. Chem. 1995, 60, 2891-2901.
26. Schaefer, T.; Baleja, J. D. Can. J. Chem. 1986, 64, 1376-1381.
27. Schaefer, T.; Penner, G. H. Can. J. Chem. 1988, 66, 1229-1238.
28. Distefano, G.; Granozzi, G.; Olivato, P. R. J. Chem. Soc., Perkin Trans. 2 1985, 2037-2040.
29. Baciocchi, E.; Gerini, M. F.; Lanzalunga, O.; Lapi, A.; Lo Piparo, M. G. Org. Biomol. Chem. 2003, 1, 422-426.
30. Hehre, W. J.; McIver, R. T. Jr.; Pople, J. A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1974, 96, 7162-7163.
31. Lin, J. L.; Huang, L. C. L.; Tzeng, W. B. J. Phys. Chem. A 2001, 105, 11455-11461.