A density functional theory study of cyclization of citronellal

Progress in Reaction Kinetics and Mechanism

Volumn 37, Issue 2, 2012, Pages 173-182

  Zardoost, Mohammad Reza ^a   Gholami, Mohammad Reza ^a,b   Irani, M ^b   Siadati, Sayed Amir ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Activation energy; Citronellal; Cyclization; Density functional theory; Isopulegol; Kinetics; Solvent effect

Indexed keywords

ACTIVATION ENERGY; CYCLIZATION; ENZYME KINETICS; RATE CONSTANTS; SOLVENTS;

CITRONELLAL; DENSITY FUNCTIONAL THEORY METHODS; DENSITY FUNCTIONAL THEORY STUDIES; HARMONIC VIBRATIONAL FREQUENCIES; ISOPULEGOL; KINETICS AND MECHANISM; SOLVENT EFFECTS; THERMODYNAMIC PARAMETER;

DENSITY FUNCTIONAL THEORY;

EID: 84864413454     PISSN: 14686783     EISSN: None     Source Type: Journal    
DOI: 10.3184/146867812X13332734805828     Document Type: Article

References (64)

1. Andrade, C.K.Z., Vercillo, O.E., Rodrigues, J.P. and Silveira, D.P. (2004) J. Braz. Chem. Soc., 15(6), 813.
2. Snider, B.B. (1991) In: Fleming, I. (ed.), Comprehensive organic synthesis, Pergamon, Oxford, Vol. 2, p. 527;
3. Mikami, K. and Shimizu, M. (1992) Chem. Rev., 92, 1021;
4. Snider, B.B. (1980) Acc. Chem. Res., 13, 426.
5. Oppolzer, W. and Snieckus, V. (1978) Angew. Chem. Int. Ed. Engl., 17, 476.
6. Hoffmann, H.M.R. (1969) Angew. Chem. Int. Ed. Engl., 8, 556.
7. Dias, L.C. (2000) Curr. Org. Chem., 4, 305.
8. Jacob, R.G., Perin, G., Loi, L.N., Pinno, C.S. and Lenardao, E.G. (2003) Tetrahedron Lett., 44, 3605.
9. Chuah, G.K., Liu, S.H., Jaenicke, S. and Harrison, L.J. (2001) J. Catal., 200, 352.
10. Yadav, G.D. and Nair, J.J. (2000) Langmuir, 16, 4072.
11. Arata, K. and Matsuura, C. (1989) Chem. Lett., 1797.
12. Takeshi, I., Yoshiki, O. and Yoji, H. (2002) European Patent EP1225163, July 24, 2002.
13. Pybus, D. and Sell, C. (eds), (1999) The chemistry of fragrances, Royal Society of Chemistry, Cambridge.
14. Sell, C.S. (2003) A fragrant introduction to terpenoid chemistry, Royal Society of Chemistry, Cambridge.
15. Swift K.A.D. (ed.) (1999) Current topics in flavors and fragrances towards a new millennium discovery, Kluwer Academic, Dordrecht.
16. Misono, M. and Nojiri, N. (1990) Appl. Cat., 64, 1.
17. Dekker, M. and Gadamasetti, K. (ed.) (1999) Process chemistry in the pharmaceutical industry, New York, NY.
18. Nakatani, Y. and Kawashima, K. (1978) Synthesis, 147.
19. Moreira, J. and Correa, A.G. (2000) J. Braz. Chem. Soc., 11, 614.
20. Schulte-Elte, K.H. and Ohloff, G. (1967) Helv. Chim. Acta, 50, 153.
21. Grignard, V. and Doeuvre, J. (1930) Compt. Rend., 190, 1164.
22. Kimura, S. (1935) Mem. Coll. Sci. Kyoto Imp. Univ., 10, 330.
23. Glass, H.B. (1938) US Patent 2, 117, 414, 1936;
24. Chem. Abstr., 32, 5160-5162.
25. Terwilliger, C.O. (1938) US Patent 2, 117, 463, 1936;
26. Chem. Abstr., 32, 5160-5163.
27. Katsura, S., Okuda, O. and Komatsu, A. (1957) Japanese Patent 8875.
28. Kuwata, T., Kumano, K., Kogami, K., Aisaka, T. and Hasegawa, T. (1966) Japanese Patent 1529, 1966;
29. Chem. Abstr., 64, 14230-a.
30. Kumanotani, K.K. (1968) Bull. Chem. Soc. Jpn., 41, 2530.
31. Bogert, M.T. and Hasselström, T. (1930) J. Am. Chem. Soc., 52, 4093.
32. Eschinazi, H.E. (1961) J. Org. Chem., 26, 3072.
33. Carlos Kleber, Z.A., Otilie, E.V., Juliana, P.R. and Denise, P.S. (2004) J. Braz. Chem. Soc., 15(6), 813.
34. Mäki-Arvela, P., Kumar, N., Nieminen, V., Sjöholm, R., Salmi, T. and Yu Murzin, D. (2004) J. Cat., 225, 155-169.
35. Boronat, M., Concepcion, P., Corma, A., Navarro, M.T., Renz, M. and Valencia, S. (2009) Phys. Chem. Chem. Phys., 2876.
36. Kukuwara, Y. et al. (2008) J. Am. Chem. Soc., 130(47), 15872.
37. Frisch, M.J., Trucks, G.W., Schlegel, H.B. et al. (2003) Gaussian, Inc., Pittsburgh PA.
38. Becke, A.D. (1988) Phys. Rev., A38, 3098.
39. Lee, C., Yang, W. and Parr, R.G. (1988) Phys. Rev., B371, 785.
40. McLean, A.D. and Chandler, G.S. (1980) J. Chem. Phys., 72, 5639.
41. Krishnan, R., Binkley, J.S., Seeger, R. and Pople, J.A. (1980) J. Chem. Phys., 72, 650.
42. Petersson, G.A. and Al-Laham, M.A. (1991) J. Chem. Phys., 94, 6081.
43. Petersson, G.A., Bennett, A., Tensfeldt, T.G., Al-Laham, M.A., Shirley, W.A. and Mantzaris, J. (1988) J. Chem. Phys., 89, 2193.
44. Peng, C., Ayala, P.Y., Schlegel, H.B. and Frisch, M.J. (1996) J. Comp. Chem., 17, 49.
45. Peng, C. and Schlegel, H.B. (1994) Israel J. Chem., 33 449.
46. Gonzalez, C. and Schlegel, H.B. (1990) J. Phys. Chem., 94, 5523.
47. Gonzalez, C. and Schlegel, H.B. (1989) J. Chem. Phys., 90, 2154.
48. Reed, A.E., Curtiss, L.A. and Weinhold, F. (1988) Chem. Rev., 88, 899.
49. Carpenter, J.E. and Weinhold, F. (1988) J. Mol. Struct.: THEOCHEM, 169, 41.
50. Glasstone, S., Laidler, K.J. and Eyring, H. (1941) The theory of rate processes, McGraw-Hill, New York.
51. Laidler, K.J. (1969) Theories of chemical reaction rates, McGraw-Hill, New York.
52. Davidson, M.M., Hillier, I.H., Hall, R.J. and Burton, N.A. (1994) J. Am. Chem. Soc., 116, 9294.
53. Pauling, L. (1947) J. Am. Chem. Soc., 9, 542.
54. Scaldaferri, M.C.L. and Pimentel, A.S. (2009) Chem. Phys. Lett., 470, 203.
55. Aggarwal, V.K., Vennal, G.P., Davey, P.N. and Newman, C. (1998) Tetrahedron Lett., 39, 1997-2001.
56. Masel, R.I. (2007) Chemical kinetics and catalysis, Chap. 13, p. 798. John Wiley and Sons.
57. Glukhoutsev, M.N., Pross, A. and Radom, L. (1995) J. Am. Chem. Soc., 117, 9012.
58. Parker, A.J. (1969) Chem. Rev., 69, 1.
59. Shieh, D.L., Tsai, C.C. and Ko, A.N. (2003) React. Kinet. Catal. Lett., 79(2), 381-389.
60. Kogami, K. and Kumanotani, J. (1968) Bull. Chem. Soc. Jpn., 41(10), 2530-2532.
61. Ingold, C.K. (1969) Structure and mechanism in organic chemistry, 2nd edn, p. 457ff. and 680ff. Cornell University Press, Ithaca/N.Y., and London.
62. Hughes E.D. and Ingold, C.K. (1935) J. Chem. Soc., 244.
63. Hughes, E.D. and Ingold, C.K. (1941) Trans. Faraday Soc., 37, 603, 657;
64. Cooper, K.A., Dhar, M.L., Hughes, E.D., Ingold, C.K., MacNulty, B.J. and Woolf, L.I. (1948) J. Chem. Soc., 2043.