A theoretical study on catalyzed ethen-1,1-diol-acetic acid tautomerizations

Journal of Molecular Structure: THEOCHEM

Volumn 468, Issue 1-2, 1999, Pages 105-117

  Sung, Kuangsen ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

1 diol ethenol; Acetaldehyde; Acetic acid; Catalyst; Ethen 1; Keto enol tautomerization

Indexed keywords

ACETALDEHYDE; ACETIC ACID; AMMONIA; ETHEN 1,1 DIOL; HYDROFLUORIC ACID; HYDROGEN SULFIDE; HYDROXYL GROUP; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; GAS; ISOMERISM; TAUTOMERIC SHIFT; THEORY; THERMODYNAMICS;

EID: 0033538835     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00519-3     Document Type: Article

References (63)

1. Z. Rappoport, The Chemistry of Enols, John Wiley and Sons, New York, 1990.
2. S. Forsen, M. Nilsson, The Chemistry of the Carbonyl Group, John Wiley and Sons, New York, 1970, vol. 2, p. 157.
3. Hart H. Chem. Rev. 79:1979;515.
4. Toullec J. Adv. Phys. Org. Chem. 18:1982;1.
5. B. Capon, D.S. Rycroft, T.W. Water, J. Chem. Soc. Chem. Commun., 1979, p. 724.
6. Capon B., Guo B.Z., Kwok F.C., Siddhanta A.K., Zucco C. Acc. Chem. Res. 21:1988;135.
7. Kresge A.J. Chemtech. 16:1986;250.
8. Chiang Y., Kresge A.J., Tang Y.S., Wirz J. J. Am. Chem. Soc. 106:1984;460.
9. Chiang Y., Kresge A.J., Wirz J. J. Am. Chem. Soc. 106:1984;6392.
10. Chiang Y., Kresge A.J., Krogh E.T. J. Am. Chem. Soc. 110:1988;2600.
11. Keefe J.R., Kresge A.J., Schepp N.P. J. Am. Chem. Soc. 110:1988;1993.
12. Chiang Y., Hojatti M., Keefe J.R., Kresge A.J., Schepp N.P., Wirz J. J. Am. Chem. Soc. 109:1987;4000.
13. Saito S. Chem. Phys. Lett. 42:1976;399.
14. Saito S. Pure Appl. Chem. 50:1978;1239.
15. Holmes J.L., Lossing F.P. J. Am. Chem. Soc. 104:1982;2648.
16. Rodler M., Bauder A. J. Mol. Struct. 97:1983;47.
17. Rodler M., Bauder A. J. Am. Chem. Soc. 106:1984;4025.
18. Albredt B., Allan M., Haselbach E., Neuhaus L. Helv. Chim. Acta. 67:1984;216.
19. Turecek F., Hanus V. Org. Mass Spectrom. 19:1984;423.
20. Turecek F., Brabec L., Korvola J. J. Am. Chem. Soc. 110:1988;7984.
21. Ripoll J.-L. Nouv. J. Chim. 3:1979;195.
22. Lasne M.-C., Ripoll J.-L. Synthesis. 1985;121.
23. McMillan G.R., Calvert J.G., Pitts N.J. J. Am. Chem. Soc. 86:1964;3602.
24. Blank B., Fischer H. Helv. Chim. Acta. 56:1973;506.
25. Rosenfeld S.M., Lawler R.G., Ward H.R. J. Am. Chem. Soc. 95:1973;946.
26. Shelly K.P., Nagarajan K., Stewart R. Can. J. Chem. 65:1987;1734.
27. Venimadhavan S., Shelly K.P., Stewart R. J. Org. Chem. 54:1989;2483.
28. Shelly K.P., Venimadhavan S., Nagarajan K., Stewart R. Can. J. Chem. 67:1989;1274.
29. Reitz O., Kopp J. Z. Phys. Chem. A184:1939;429.
30. Swain C.G., Stivers E.C., Reuwer J.E., Schaad L.J. J. Am. Chem. Soc. 80:1958;5885.
31. Capon B., Zucco C. J. Am. Chem. Soc. 104:1982;7564.
32. Shelly K., Nagarajan K., Stewart R. Can. J. Chem. 65:1987;1734.
33. Hine J., Kaufman J.C., Cholod M.S. J. Am. Chem. Soc. 94:1972;4590.
34. Chiang Y., Kresge A.J., Walsh P.A. Z. Naturforsch. 44A:1989;406.
35. Gerlt J.A., Gassman P.G. J. Am. Chem. Soc. 115:1993;11 552-11 568.
36. Klopman G., Andreozzi P. Bull. Soc. Chim. Belg. 88:1979;875.
37. Lledos A., Bertran J., Ventura O.N. Int. J. Quantum Chem. 30:1986;467.
38. Bertran J., Lledos A., Revetllat J.A. Int. Quantum Chem. 23:1983;587.
39. Andraos J., Chiang Y., Kresge A.J., Pojarlieff I.G., Schepp N.P., Wirz J. J. Am. Chem. Soc. 116:1994;73-81.
40. Andraos J., Chiang Y., Kresge A.J., Scaiano J.C. J. Am. Chem. Soc. 115:1993;10 605-10 610.
41. Andraos J., Chiang Y., Kresge A.J., Popik V.V. J. Am. Chem. Soc. 119:1997;8417-8424.
42. Gaussian 94 (Revision D.2): M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T.A. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian, Inc., Pittsburgh, PA, 1995.
43. Pople J.A., Scott A.P., Wong M.W., Radom L. Isr. J. Chem. 33:1993;345.
44. Jorgensen W.L., Lim D., Blake J.F. J. Am. Chem. Soc. 115:1993;2936-2942.
45. Mas E.M., Szalewicz K. J. Chem. Phys. 104:1996;7606.
46. Scheiner S. Ann. Rev. Phys. Chem. 45:1994;23.
47. Curtiss L.A., Frurip D.J., Blande M. J. Chem. Phys. 71:1979;2703.
48. Reimers J., Watts R., Klein M. Chem. Phys. 64:1982;95.
49. Kunttu H., Dahiquis M., Murto J., Rasanen M. J. Phys. Chem. 92:1988;1945.
50. Apeloig Y., Arad D., Rappoport Z. J. Am. Chem. Soc. 112:1990;9131-9140.
51. Greenberg A., Steveson T.A. J. Am. Chem. Soc. 107:1985;3488.
52. Rodler M., Bauder A. J. Am. Chem. Soc. 106:1984;4025.
53. Saito S. Pure Appl. Chem. 50:1978;1239.
54. Kaushik V.K. Chem. Phys. Lett. 49:1977;255.
55. Capon B., Siddhanta A.K. J. Org. Chem. 49:1984;80.
56. Capon B., Siddhanta A.K. Tetrahedron Lett. 23:1982;3189.
57. Nguyen M.T., Hegarty A.F. J. Am. Chem. Soc. 106:1984;1552.
58. The enthalpy of ketonization of ethenol may be obtained from heat of formation of ethenol [46] and acetaldehyde [47].
59. Holmes J.L., Terlouw J.K., Lossing F.P. J. Phys. Chem. 80:1976;2860.
60. J.F. Cox, D. Pilcher, Thermochemistry of Organic and Organometallic Compounds; Academic Press, New York, 1970.
61. Holmes J.L., Lossing F.P. J. Am. Chem. Soc. 104:1982;2649-2652.
62. Ladanyi B.M., Hynes J.T. J. Am. Chem. Soc. 108:1986;598.
63. A.J. Gordon, R.A. Ford, The Chemist's Companion: A Handbook of Practical Data, Techniques and References, John Wiley and Sons, New York, 1972, pp. 60-62.