Ab initio theoretical investigation on the reactivity as bases of mixed LiMe/KOMe complexes. A model for Schlosser LICKOR superbase

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 7053-7062

  Ghigo, Giovanni ^a   Tonachini, Glauco ^a   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE;

ARTICLE; COMPLEX FORMATION; PRIORITY JOURNAL; THEORY;

EID: 0029932370     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00310-9     Document Type: Article

References (35)

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2. Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. Mordini, A. in Advances in Carbanion Chemistry, V. Snieckus Ed.; JAI Press Inc., Greenwich CT, London 1992, p 1-44.
3. Schlosser, M. J. Organomet. Chem. 1967, 8, 9-16.
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7. Gilman, H.; Bailie, I. C. J. Org. Chem. 1937, 2, 84. Schlosser, M.; Choi, I. H.; Takagishi, S. Tetrahedron 1990, 46, 5633-5648.
8. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 5458-5462. Prandi, C.; Venturello, P. Tetrahedron 1994, 50, 12463-12468, and references cited therein.
9. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 5458-5462. Prandi, C.; Venturello, P. Tetrahedron 1994, 50, 12463-12468, and references cited therein.
10. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Prandi, C.; Venturello, P. J. Org. Chem. 1994, 59, 5458-5462. Prandi, C.; Venturello, P. Tetrahedron 1994, 50, 12463-12468, and references cited therein.
11. Bailey, W. F.; Zartun, D. L. J. Chem. Soc., Chem. Commun. 1984, 34-35.
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13. (a) t-BuLi has been shown to exist as a monomer in THF: Bauer, W.; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371-2379. Here MeLi is considered just as a simple model for BuLi.
14. (b) About the oligomerization of alkyllithiums, see: Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometallics 1989, 8, 2577-2584; Kaufmann, E.; Raghavachari, K.; Reed, A. E.; Schleyer, P. v. R. Organometallics 1988, 7, 1597-1607 and references therein.
15. (b) About the oligomerization of alkyllithiums, see: Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometallics 1989, 8, 2577-2584; Kaufmann, E.; Raghavachari, K.; Reed, A. E.; Schleyer, P. v. R. Organometallics 1988, 7, 1597-1607 and references therein.
16. (c) Introduction of heteroatoms affects significantly the anion-cation interactions which determine the tendency to give aggregates: Canepa, C.; Antoniotti, P.; Tonachini, G. Tetrahedron 1994, 50, 8073-8084; Canepa, C.; Tonachini, G. Tetrahedron 1994, 50, 12511-12520.
17. (c) Introduction of heteroatoms affects significantly the anion-cation interactions which determine the tendency to give aggregates: Canepa, C.; Antoniotti, P.; Tonachini, G. Tetrahedron 1994, 50, 8073-8084; Canepa, C.; Tonachini, G. Tetrahedron 1994, 50, 12511-12520.
18. Schlegel, H. B. in Computational Theoretical Organic Chemistry Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
19. Schlegel, H. B. in Computational Theoretical Organic Chemistry Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
20. Schlegel, H. B. in Computational Theoretical Organic Chemistry Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
21. Schlegel, H. B. in Computational Theoretical Organic Chemistry Csizsmadia, I. G.; Daudel, R. Eds. Reidel Publ. Co.: Dordretch 1981, 129. Schlegel, H. B. J. Chem. Phys. 1982, 77, 3676-3681. Schlegel, H. B.; Binkley, J. S.; Pople, J. A. J. Chem. Phys. 1984, 80, 1976-1981. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
22. (a) Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939-947.
23. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
24. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
25. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
26. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
27. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229-236. Pople, J. A; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1-19. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91-100.
28. (a) Huzinaga, S.; Andzelm, J.; Klobukowski, M.; Radzio-Andzelm, E.; Sakai, Y.; Tatewaki, H. "Gaussian Basis Sets for Molecular Calculations" in Physical Sciences Data 16, Elsevier, 1984.
29. (b) For K / C and O / Li / H, repectively, the basis consists of (13s,8p / 7s,5p,1d / 7s,1p / 4s) gaussians, respectively, which are grouped as: 43321 (s) and 431 (p, the last one a polarization function) for K; 421 (s), 311 (p, the last one a diffuse function), and 1 (d, the polarization set) for C and O; 421 (s), 1 (p, a polarization function) for Li; 31 (s) for H. This provides a [53/331/31/2] basis set.
30. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
31. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
32. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1983, 78, 4066-4073. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218.
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34. Ghigo, G. Tesi di Laurea, Università di Torino, 1994.
35. Ghigo, G.; Tonachini, G.; Fossey, J. to be published.