Studies on the Toxic Oil Syndrome: proposal of a mechanism for the thermal conversion of 3-N-phenylamino-1,2-propanediol esters into anilides under deodorisation conditions

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 418-426

  Escabrós, Jordi ^a   Crehuet, Ramon ^a   Messeguer, Angel ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

Author keywords

3 N Phenylamino 1,2 propanediol esters; Anilides; Computational studies; Deodorisation; Reaction mechanism; Toxic Oil Syndrome

Indexed keywords

AMINE; ANILIDE; ESTER DERIVATIVE;

ARTICLE; DECOMPOSITION; ELIMINATION REACTION; ENERGY; HYDROLYSIS; ISOMER; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; THERMOSTABILITY; TOXIC OIL SYNDROME;

EID: 56949093535     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.102     Document Type: Article

References (40)

1. Posada de la Paz M., Philen R.M., and Abaitua Borda I. Epidemiol. Rev. 23 (2001) 231-247
2. Diggle G.E. Int. J. Clin. Pract. 55 (2001) 371-375
3. Pestaña A., and Muñoz E. Nature 298 (1982) 608
4. Ventura Díaz L.M. Grasas y Aceites 33 (1982) 73-78
5. Gradjean, P.; Tarkowski, S. Toxic Oil Syndrome. Mass Food Poisoning in Spain. WHO Regional Office for Europe: Copenhagen, Denmark, 1984, pp 3-16.
6. Vázquez-Roncero A., Janer del Valle C., Maestro Durán R., and Graciani Constante E. Lancet ii (1983) 1024-1025
7. Vázquez-Roncero A., Maestro Durán R., and Gutiérrez R. Grasas y Aceites 35 (1984) 15-21
8. Vázquez Roncero A., and Gómez Gómez R. Grasas y Aceites 38 (1987) 87-92
9. Posada de la Paz M., Philen R.M., Schurz H., Hill R.H.J., Giménez Ribota O., Gómez de la Cámara A., Kilbourne E.M., and Abaitua Borda I. Epidemiology 10 (1999) 130-134
10. Schurz H.H., Hill R.H., Posada de la Paz M., Philen R.M., Borda I.A., Bailey S.L., and Needham L.L. Chem. Res. Toxicol. 9 (1996) 1001-1006
11. Ladona M.G., Bujons J., Messeguer A., Ampurdanés C., Morató A., and Corbella J. Chem. Res. Toxicol. 12 (1999) 1127-1137
12. Bujons J., Ladona M.G., Messeguer A., Morató A., and Ampurdanés C. Chem. Res. Toxicol. 14 (2001) 1097-1106
13. Morató A., Martínez-Cabot A., Escabrós J., Bujons J., and Messeguer A. Chem. Res. Toxicol. 17 (2004) 889-895
14. Morató A., Escabrós J., Manich A., Reig N., Castaño Y., Abian J., and Messeguer A. Chem. Res. Toxicol. 18 (2005) 665-674
15. Martínez-Cabot A., Morató A., and Messeguer A. Chem. Res. Toxicol. 18 (2005) 1721-1728
16. Martinez-Cabot A., and Messeguer A. Chem. Res. Toxicol. 20 (2007) 1556-1562
17. Reig N., Calaf R.E., Castaño Y., Prieto R., Messeguer A., Morató A., Escabrós J., Gelpí E., and Abian J. J. Mass Spectrom. 42 (2007) 527-541
18. Ruíz-Méndez M.V., Posada de la Paz M., Abian J., Calaf R.E., Blount B., Castro-Molero N., Philen R., and Gelpí E. Food Chem. Toxicol. 39 (2001) 91-96
19. Chalmet S., Harb W., and Ruiz-López M.F. J. Phys. Chem. 105 (2001) 11574-11581
20. Gorb L., Asensio A., Tuñón I., and Ruiz-López M.F. Chem.-Eur. J. 11 (2005) 6743-6753
21. Cascella M., Raugei S., and Carloni P. J. Phys. Chem. B 108 (2004) 369-375
22. Zahn D. Eur. J. Org. Chem. 69 (2004) 4020-4023
23. Crehuet R., Anglada J.M., and Bofill J.M. Chem.-Eur. J. 7 (2001) 2227-2235
24. Anglada J.M., Aplincourt P., Bofill J.M., and Cremer D. ChemPhysChem 2 (2002) 215-221
25. Aplincourt P., and Anglada J.M. J. Phys. Chem. 107 (2003) 5812-5820
26. Dewar M.J.S. J. Am. Chem. Soc. 106 (1984) 209-219
27. Eriksson M.A., Hard T., and Nilsson L. Biophys. J. 69 (1995) 329-339
28. Ciarkowski J., Chen F.M.F., and Benoiton N.L. J. Comput.-Aided Mol. Des. 5 (1991) 599-616
29. Adamo C., Cossi M., and Barone V. J. Comput. Chem. 18 (1997) 1993-2001
30. Hwa D.-H., and Ho J.-J. J. Phys. Chem. 102 (1998) 3582-3586
31. Carey F.A., and Sundberg R.J. Advanced Organic Chemistry: Structure and Mechanisms (2000), Plenum: New York, NY, USA
32. Ferrer M., Galceran M., Sánchez-Baeza F., Casas J., and Messeguer A. Liebigs Ann. Chem. (1993) 507-511
33. Becke A.M. J. Chem. Phys. 98 (1993) 5648-5652
34. Granovsky, A. A. PC GAMESS version 7.0, http://classic.chem.msu.su/gran/gamess/index.html.
35. Tomasi J., Mennucci B., and Cammi R. Chem. Rev. 105 (2005) 2999-3094
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; 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.; Gonzalez, C.; Pople, J. A. Gaussian 03. Revision C.02. Gaussian: Wallingford, CT, USA.
37. Kumar S., Rosenberg J.M., Bouzida D., Swendsen R.H., and Kollman P.A. J. Comput. Chem. 13 (1992) 1011-1021
38. Roux B. Comput. Phys. Commun. 91 (1995) 275-282
39. Field M.J., Céline M.A., Proust-De B.F., and Thomas M.A. J. Comput. Chem. 21 (2000) 1088-1100
40. Field M.J. A Practical Introduction to the Simulation of Molecular Systems (1999), Cambridge University Press Cambridge, UK