Tautomers of Monothioacetylacetone: A Combined ab initio and Density Functional Study

Zeitschrift fur Physikalische Chemie

Volumn 209, Issue Part_1, 1999, Pages 75-92

  Fischer, G ^a   Fabian, J ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CALCULATIONS; CHELATION; CHEMICAL SHIFT; DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; GROUND STATE; QUANTUM CHEMISTRY; QUANTUM THEORY;

AB INITIO; ENOL-ENETHIOL TAUTOMERISM; INTRAMOLECULAR HYDROGEN BONDING; MOLECULAR GROUND STATE; NATURAL RESONANCE; NMR CHEMICAL SHIFTS;

HYDROGEN BONDS;

EID: 0041992610     PISSN: 09429352     EISSN: None     Source Type: Journal    
DOI: 10.1524/zpch.1999.209.Part_1.075     Document Type: Article

References (57)

1. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer Verlag, New York 1991.
2. J.-M. Lehn, Supramolecular Chemistry. Concepts and Perspectives, VCH Pubi., New York (1995).
3. J. Emsley, Struct Bonding 157 (1984) 147;
4. F. Hibbert and J. Emsley, Adv. Phys. Org. Chem. 26 (1990) 255 and references therein.
5. P. Schuster, Top. Curr. Chem. 120 (1984) 35;
6. Encyclop. Phys. Sci. Techn. 7 (1992) 727.
7. G. Gilli, F. Beliucci, F. Ferretti and V. Bertolasi, J. Am. Chem. Soc. 111 (1989) 1023;
8. V. Bertolasi, P. Gilli, V. Ferretti and G. Gilli, J. Chem. Soc. Perkin Trans. 2, 1997, 945.
9. K. Iljima, A. Ohnogi and S. Shibata, J. Mol. Struct. 156 (1987) 111 and references therein.
10. A. Camerman, D. Mastropaolo and N. Camerman, J. Am. Chem. Soc. 105 (1983) 1584.
11. M. J. Frisch, A. C. Scheiner, H. F. Schaeffer III and J. St. Binkley, J. Chem. Phys. 82 (1985) 4194.
12. O. A. Sharafeddin, K. Hinsen, T. Carrington, Jr. and B. Roux, J. Comput. Chem. 14 (1997) 1780 and references therein.
13. R. Mayer, G. Hiller, M. Nitzschke and J. Jentzsch, Angew. Chem. 75 (1963) 1011;
14. F. Duus and J. W. Anthonsen, Acta Chem. Scand. B31 (1977) 40.
15. J. Fabian, Tetrahedron 29 (1973) 2449.
16. F. Duus, in Compreh. Org. Chem., Vol. 3, Chapt. 11.22, eds. D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford 1979;
17. B. Floris, in The Chemistry of Enols, pp. 285, ed. Z. Rappoport 1991, J. Wiley, Chichester (1990).
18. F. Duus, J. Am. Chem. Soc. 108 (1986) 630;
19. U. Berg, J. Sandström, L. Carlsen and F. Duus, J. Chem. Soc. Perkin Trans. 2, 1983, 1321;
20. F. S. J0rgensen, R. S. Brown, L. Carlsen and F. Duus, J. Am. Chem. Soc. 104 (1982) 5922;
21. L. Carlsen and F. Duus, J. Chem. Soc. Perkin Trans. 2, 1979, 1532.
22. S. Millefiori and A. Millefiori, J. Chem. Soc. Faraday Trans. 2, 2 (1989) 1465; cf.
23. S. Millefiori and S. Di Bella, J. Chem. Soc. Faraday Trans. 87 (1990) 1297.
24. J. S. Craw and G. B. Bacskay, J. Chem. Soc. Faraday Trans. 88 (1992) 2315;
25. cf. A. N. Dixit, K. V. Reddy, A. R. A. S. Deshmukh, S. Rajappa, B. Ganguly and J. Chandrasekhar, Tetrahedron 51 (1995) 1437.
26. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York (1986);
27. A. Szabo and N. S. Ostlund, Modem Quantum Chemistry, McGraw-Hill, New York (1989);
28. R. H. Bartlett and J. F. Stanton, in Rev. Comput. Chem., Vol. 5, eds. K. B. Lipkowitz and D. B. Boyd, VCH Pubi., New York (1994) and references therein.
29. R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York (1989);
30. W. Kohn, A. D. Becke and R. G. Parr, J. Phys. Chem. 100 (1995) 12974 and references therein.
31. Gaussian 94, Revision B.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. 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. Nanay akkara, 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 and J. A. Pople, Gaussian, Inc., Pittsburgh PA, USA (1995).
32. L. A. Curtiss, K. Raghavachari and J. A. Pople, J. Chem. Phys. 98 (1993) 1293;
33. L. A. Curtiss, K. Raghavachari, P. C. Redfem, J. A. Pople, J. Chem. Phys. 106 (1997) 1063 and references therein;
34. J. W. Ochterski, C. A. Peterson and K. B. Wiberg, J. Am. Chem. Soc. 117 (1995) 11299.
35. A. D. Becke, J. Chem. Phys. 98 (1993) 1372, 5648;
36. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B37 (1988) 785, Implementation in GAUSSIAN-94:
37. P. J. Stephens, F. J. Devlin, C. F. Chabalowski and M. J. Frisch, J. Phys. Chem. 98 (1994) 11623.
38. N. Oliphant and R. J. Bartlett, J. Chem. Phys. 100 (1994) 6550;
39. C. W. Bauschlicher, Jr., Chem. Phys. Lett. 246 (1995) 40.
40. B. Ma, J.-H. Lii, H. F. Schaefer III and N. L. Allinger, J. Phys. Chem. 100 (1996) 8763.
41. P. Geerling, F. De Proft and M. L. Martin, in Recent Developments and Applications of Modem Density Functional Theory; pp. 773, ed. J. M. Seminario, Elsevier, Amsterdam (1996).
42. V. Barone and C. Adamo, J. Chem. Phys. 105 (1996) 1107.
43. A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev. 88 (1988) 899.
44. Program Packet NBO 4.0, E. D. Glendening, J. K. Badenhoop, A. A. Reed, J. E. Carpenter and F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison (1996).
45. E. D. Glendening, J. K. Badenhoop and F. Weinhold, in Nataural Resonance Theory, WISTCI-803, Theoretical Chemistry Institute, University of Wisconsin, Madison (1994).
46. R. Dietchfield, Mol. Phys. 27 (1974) 789.
47. J. Gauss, Ber. Bunsenges. Phys. Chem. 99 (1995) 1001;
48. J. R. Cheeseman, G. W. Trucks, T. A. Keith and M. Frisch, J. Chem. Phys. 104 (1996) 5497;
49. D. P. Chesnut, in Reviews of Computational Chemistry; Vol. 8, eds. K. B. Lipkowitz and D. B. Boyd, VCH, New York 1996.
50. P. v. R. Schleyer, P. K. Freeman, H. Jiao and B. Goldfuss, Angew. Chem. 108 (1996) 2548;
51. P. v. R. Schleyer, C. Maerker, A. Deanfeld, H. Jiao and N. J. R. van Eikeme Hommes, J. Am. Chem. Soc. 118 (1996) 6317.
52. L. Norskov-Lauritsen, L. Carlson and F. Duus, J. Chem. Soc. Chem. Commun. 1983, 496.
53. L. F. Power, K. E. Turner and F. H. Moore, J. Chem. Soc. Perkin Trans. 2, 1976 249.
54. N. Tyutuylkov, J. Fabian, A. Mehlhom, F. Dietz and A. Tadjer, Polymethine. Structure and Properties, St. Kliment Ohridski Univ. Press, Sofia (1991).
55. M. Garcia-Viloca, A. Gonzáles-Lafont and J. M. Lluch, J. Am. Chem. Soc. 119 (1997) 1081.
56. L. Carlson and F. Duus, J. Am. Chem. Soc. 100 (1978) 281.
57. E. Liepens, M. V. Petrova, E. Grudriniece, J. Paulins and S. L. Kuznetsov, Magn. Reson. Chem. 27 (1989) 907.