Theoretical study of the thermolysis reaction of methyl β-hydroxycarboxylates in the gas phase

Journal of Physical Organic Chemistry

Volumn 17, Issue 4, 2004, Pages 294-302

  Sánchez, Claudia ^a,b   Quijano, Jairo ^b   Notario, Rafael ^c  

^a Jaime Isaza Cadavid   (Colombia)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

Ab initio theoretical methods; Gas phase; Kinetics; Methyl hydroxycarboxylates; Thermolysis

Indexed keywords

ACTIVATION ENERGY; DECOMPOSITION; GASES; ISOTOPES; MONOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

GAS PHASE; THERMOLYSIS;

AROMATIC COMPOUNDS;

EID: 16544373020     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.727     Document Type: Article

References (48)

1. Klabunovskii EI. Russ. Chem. Rev. 1996; 65: 329-344.
2. Notario R, Quijano J, Quijano JC, Gutiérrez LP, Suárez WA, Sánchez C, Leon LA, Chamorro E. J. Phys. Chem. A 2002; 106: 4377-4383.
3. August R, McEwen I, Taylor R. J. Chem. Soc., Perkin Trans. 2 1987; 1683-1689.
4. Kao J. J. Mol. Struct (Theochem) 1988; 180: 383-387.
5. Lee I, Cha OJ, Lee BS. Bull. Korean Chem. Soc. 1991; 12: 97-101.
6. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andrés JL, González C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.11.3. Gaussian: Pittsburgh, PA, 2001.
7. Møller C, Plesset M. Phys. Rev. 1934; 46: 618-622.
8. Ditchfield R, Hehre WJ, Pople JA. J. Chem. Phys. 1971; 54: 724-728.
9. Scott PA, Radom L. J. Phys. Chem. 1996; 100: 16502-16513.
10. McQuarrie DA, Simon JD. Molecular Thermodynamics. University Science Books: Sausalito, CA, 1999.
11. McIver JV Jr. Acc. Chem. Res. 1974; 7: 72-77.
12. Fukui K. J. Phys. Chem. 1970; 74: 4161-4163.
13. Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PvR. J. Comput. Chem. 1983; 4: 294-301.
14. Reed AE, Weinhold F. J. Chem. Phys. 1983; 78: 4066-4073.
15. Reed AE, Curtiss LA, Weinhold F. Chem. Rev. 1988; 88: 899-926.
16. Wiberg KB. Tetrahedron 1968; 24: 1083-1096.
17. Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBO, Version 3.1. Madison, WI, 1988.
18. Glasslone KJ, Laidler KJ, Eyring H. The Theory of Rate Processes. McGraw-Hill: New York, 1941; chapt. 4.
19. Benson SW. The Foundations of Chemical Kinetics. McGraw-Hill: New York, 1969.
20. Woolen JB, Houminer Y. J. Org. Chem. 1982; 47: 5102-5106.
21. Quijano J, Notario R, Chamorro E, León LA, Sánchez C, Alarcón G, Quijano JC, Chuchani G. J. Phys. Org. Chem. 2002; 15: 413-419.
22. Chamorro E, Quijano J, Notario R, Sánchez C, León LA, Chuchani G. Int. J. Quantum Chem. 2003; 91: 618-625.
23. Notario R, Quijano J, León LA, Sánchez C, Quijano JC, Alarcón G, Chamorro E, Chuchani G. J. Phys. Org. Chem. 2003; 16: 166-174.
24. Moyano A, Pericàs MA, Valentí E. J. Org. Chem. 1989; 54: 573-582.
25. Domingo LR, Picher MT, Safont VS, Andrés J, Chuchani G. J. Phys. Chem. A 1999; 103: 3935-3943.
26. Domingo LR, Andrés J, Moliner V, Safont VS. J. Am. Chem. Soc. 1997; 119: 6415-6422.
27. Toullec J. Adv. Phys. Org. Chem. 1982; 18: 1-77.
28. Rappoport Z. The Chemistry of Enols. Wiley: New York, 1990.
29. Chiang Y, Kresge AJ, Schepp NP. J. Am. Chem. Soc. 1989; 111: 3977-3980.
30. Keeffe JR, Kresge AJ, Schepp NP. J. Am. Chem. Soc. 1990; 112: 4862-4868.
31. Chiang Y, Kresge AJ, Pruszynski P. J. Am. Chem. Soc. 1992; 114: 3103-3107.
32. Andraos J, Kresge AJ, Popik VV. J. Am. Chem. Soc. 1994; 116: 961-967.
33. Chiang Y, Kresge AJ, Schepp NP, Xie R-Q. J. Org. Chem. 2000; 65: 1175-1180.
34. Chiang Y, Griesbeck AG, Heckroth H, Hellrung B, Kresge AJ, Meng Q, O'Donoghue AC, Richard JP, Wirz J. J. Am. Chem. Soc. 2001; 123: 8979-8984.
35. Andrés J, Domingo LR, Picher MT, Safont VS. Int. J. Quantum Chem. 1998; 66: 9-24.
36. Saito S. Chem. Phys. Lett. 1976; 42: 399-402.
37. Rodler M, Bauder A. J. Am. Chem. Soc. 1984; 106: 4025-4028.
38. Rodler M, Blom CE, Bauder A. J. Am. Chem. Soc. 1984; 106: 4029-4035.
39. Apeloig Y. In The Chemistry of Enols, Rappoport Z (ed). Wiley: New York, 1990; chapt. 1.
40. Wu C-C, Lien M-H. J. Phys. Chem. 1996; 100: 594-600.
41. Taft RW, Topsom RD. Prog. Phys. Org. Chem. 1987; 16: 1-84.
42. Taft RW, Koppel IA, Topsom RD, Anvia F. J. Am. Chem. Soc. 1990; 112: 2047-2052.
43. Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165-195.
44. Melander L. Isotope Effects on Reaction Rates. Ronald: New York, 1960.
45. Melander L, Saunders WH Jr. Reaction Rates of Isotopic Molecules. Krieger: Malabar, FL, 1987.
46. Westheimer FH. Chem. Rev. 1961; 61: 265-273.
47. More O'Ferrall RA. J. Chem. Soc. B 1970; 785-790.
48. Streitweiser A Jr, Jagow RH, Fahey RC, Suzuki S. J. Am. Chem. Soc. 1958; 80: 2326-2332.