On the pyrolysis mechanism of 2-pyranones and 2-pyranthiones: Thermally induced ground electronic state chemistry of pyran-2-thione

Journal of Organic Chemistry

Volumn 70, Issue 19, 2005, Pages 7701-7710

  Reva, Igor ^a   Breda, Susana ^a   Roseiro, Teresa ^a   Eusébio, Ermelinda ^a   Fausto, Rui ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFERENTIAL SCANNING CALORIMETRY; ELECTRONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GROUND STATE; INFRARED SPECTROSCOPY; SULFUR;

INFRARED SPECTRUM; PYRAN-2-THIONE (PT); THERMOCHEMISTRY; THIAPYRENE-2-ONE (TP);

PYROLYSIS;

2 PYRANTHIONE; 2 PYRONE DERIVATIVE; ARGON; OXYGEN; PYRAN 2 THIONE; PYRAN DERIVATIVE; SULFUR; THIAPYRAN 2 ONE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BOND; DIFFERENTIAL SCANNING CALORIMETRY; FOURIER TRANSFORMATION; HEATING; INFRARED SPECTROSCOPY; LOW TEMPERATURE PROCEDURES; PYROLYSIS; RING OPENING; THERMOSTABILITY;

EID: 24944524915     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051100w     Document Type: Article

References (34)

1. Pirkle, W. H.; McKendry, L. H. J. Am. Chem. Soc. 1969, 91, 1179-1186.
2. Pong, R. G. S.; Huang, B. S.; Laureni, J.; Krantz, A. J. Am. Chem. Soc. 1977, 99, 4153-4154.
3. Pong, R. G. S.; Shirk, J. S. J. Am. Chem. Soc. 1973, 95, 248-249.
4. Huang, B. S.; Pong, R. G. S.; Laureni, J.; Krantz, A. J. Am. Chem. Soc. 1977, 99, 4154-4156.
5. Pirkle, W. H.; Turner, W. V. J. Org. Chem. 1975, 40, 1617-1620.
6. Pirkle, W. H.; Turner, W. V. J. Org. Chem. 1975, 40, 1644-1646.
7. Pirkle, W. H.; Dines, M. J. Am. Chem. Soc. 1968, 90, 2318-2323.
8. Pirkle, W. H.; Seto, H.; Turner, W. V. J. Am. Chem. Soc. 1970, 92, 6984-6985.
9. Breda, S.; Reva, I.; Lapinski, L.; Fausto, R. ChemPhysChem 2005, 6, 602-604.
10. Michaut, X.; Vasserot, A. M.; Abouaf-Marguin, L. Vib. Spectrosc. 2004, 34, 83-93.
11. Lang, V. I.; Winn, J. S. J. Chem. Phys. 1991, 94, 5270-5274.
12. 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.; Baboul, A. G.; 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.; 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; Gaussian, Inc.: Pittsburgh, PA, 1998.
13. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
14. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
15. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
16. Latajka, Z.; Bouteiller, Y.; Scheiner, S. Chem. Phys. Lett. 1995, 234, 159-164.
17. Nguyen, M. T.; Creve, S.; Vanquickenborne, L. G. J. Phys. Chem. 1996, 100, 18422-18425.
18. Somnitz, H.; Zellner, R. Phys. Chem. Chem. Phys. 2000, 2, 1899-1905.
19. Scheiner, S. Acc. Chem. Res. 1985, 18, 174-180.
20. Barone, V.; Adamo, C. J. Chem. Phys. 1996, 105, 11007-11019.
21. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
22. Foresman, J. B.; Headgordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135-149.
23. Peng, C. Y.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56.
24. Birney, D. M. J. Org. Chem. 1996, 61, 243-251.
25. Chamorro, E.; Quijano, J.; Notario, R.; Sánchez, C.; León, L. A.; Chuchani, G. Int. J. Quantum Chem. 2003, 91, 618-625.
26. Chuchani, G.; Marquez, E.; Herize, A.; Domínguez, R. M.; Tosta, M.; Brusco, D. J. Phys. Org. Chem. 2003, 16, 839-848.
27. Zhang, J.; Xiao, H. M. J. Chem. Phys. 2002, 116, 10674-10683.
28. Eaton, P. E.; Gilardi, R. L.; Zhang, M. X. Adv. Mater. 2000, 12, 1143-1148.
29. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 2511-2513.
30. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. 1969, 8, 781-853.
31. Reva, I. D.; Stepanian, S. G.; Adamowicz, L.; Fausto, R. J. Phys. Chem. A 2001, 105, 4773-4780.
32. Reva, I. D.; Jarmelo, S.; Lapinski, L.; Fausto, R. J. Phys. Chem. A 2004, 108, 6982-6989.
33. Nunes, S. C. C.; Eusébio, M. E.; Leitão, M. L. P.; Redinha, J. S. Int. J. Pharm. 2004, 285, 13-21.
34. Sabbah, R.; An, X. W.; Chickos, J. S.; Leitào, M. L. P.; Roux, M. V.; Torres, L. A. Thermochim. Acta 1999, 331, 93-204.