Density functional calculations of methyllithium, t-butyllithium, and phenyllithium oligomers: Effect of hyperconjugation on conformation

Journal of Physical Chemistry A

Volumn 105, Issue 5, 2001, Pages 913-922

  Kwon, Ohyun ^a   Sevin, Fatma ^a,b   McKee, Michael L ^a  

^a AUBURN UNIVERSITY   (United States)

^b HACETTEPE UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

APPROXIMATION THEORY; CALCULATIONS; CHEMICAL BONDS; GEOMETRY; LITHIUM COMPOUNDS; OPTIMIZATION; PROBABILITY DENSITY FUNCTION;

BUTYLLITHIUM; HYPERCONJUGATION; METHYLLITHIUM; NATURAL POPULATION ANALYSIS; PHENYLLITHIUM;

OLIGOMERS;

EID: 0035250099     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp003345c     Document Type: Article

References (52)

1. Wakefield, B. J. The Chemistry of Organolithium Compounds, Pergamon: Oxford, 1974.
2. Brandsma, L.; Verkruijsse, H. D. Preparative Polar Organometallic Chemistry; Springer: Berlin, 1987; Vol. 1.
3. Lambert, C.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1994, 35, 1129.
4. Lithium Chemistry: A Theoretical and Experimental Overview; Sapse, A.-M.; Schleyer, P. v. R., Eds., Wiley: New York, 1995.
5. Weiss, E.; Hencken, G. J. Organomet. Chem. 1970, 21, 265.
6. Köster, H.; Thoennes, D.; Weiss, E. J. Organomet. Chem. 1978, 160, 1.
7. Landro, F. J.; Gurak, J. A.; Chinn, J. W., Jr.; Lagow, R. J. J. Organomet. Chem. 1983, 249, 1.
8. Chinn, J. W., Jr.; Lagow, R. J. Organometallics 1984, 3, 75.
9. Plavšić, D.; Srzić, D.; Klasinc, L. J. Phys. Chem. 1986, 90, 2075.
10. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
11. Bauer, W.; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371.
12. Darensbourg, M. Y.; Kimura, B. Y.; Hartwell, G. E.; Brown, T. L. J. Am. Chem. Soc. 1970, 92, 1236.
13. McLean, W.; Munoy, P. T.; Jarnagin, R. C. J. Chem. Phys. 1978, 69, 2715.
14. Scowell, W. M.; Kimura, B. Y.; Spiro, T. G. J. Coord. Chem. 1971, 1, 107.
15. Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
16. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1984, 107, 1805.
17. Kottke, T.; Stalke, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 580.
18. Baird, N. C.; Barr, R. F.; Datta, R. K. J: Organomet. Chem. 1973, 59, 65.
19. Clark, T.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1978, 137.
20. Graham, G.; Richtsmeier, S.; Dixon, D. A. J. Am. Chem. Soc. 1980, 102, 5759.
21. Herzig, L.; Howell, J. M.; Sapse, A. M.; Singman, E.; Snyder, G. J. Chem. Phys. 1982, 77, 429.
22. Kaufmann, E.; Raghavachari, K.; Reed, A. E.; Schleyer, P. v. R. Organometallics 1988, 7, 1597.
23. Pratt, L. M.; Khan, I. M. J. Comput. Chem. 1995, 16, 1067.
24. Koizumi, T.; Kikuchi, O. Organometallics, 1995, 14, 987.
25. Bickelhaupt, F. M.; Hommes, N. J. R. v. E.; Guerra, C. F.; Baerends, E. J. Organometallics 1996, 15, 2923.
26. Cooper, D. L.; Gerratt, J.; Karadakov, P. B.; Raimondi, M. J. Chem. Soc., Faraday Trans. 1995, 91, 3363.
27. Kirschenbaum, L. J.; Howell, J. M. Struct. Chem. 1998, 9, 327.
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, F.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.; Pittsburgh, PA, 1998.
29. Pair, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules, Oxford University Press: Oxford, 1989.
30. Abbotto, A.; Streitwieser, A.; Schleyer, P. v. R. J. Am. Chem. Soc. 1997, 119, 11255.
31. Kwon, O.; Kwon, Y. THEOCHEM 1997, 401, 133.
32. Pratt, L. M.; Streitwieser. A. J. Org. Chem. 2000, 65, 290.
33. Hobza, P.; Sponer, J.; Reschel, T. J. Comput. Chem. 1995, 16, 1315.
34. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
35. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
36. (b) Reed, A.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
37. (c) Weinhold, F. A. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley Publishers: New York, 1998; Vol. 3; pp 1792-1810.
38. -5). When diffuse functions were removed from lithium atoms, the NBO analysis completed normally. We tested the NBO analysis at the B3LYP/6-31+G(d) level for methyllithium with and without diffuse functions on lithium and found very little difference in the NPA charges or second-order perturbation energies.
39. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899, 4907.
40. MOPAC: Stewart, J. J. P. QCPE 1985, 5, 455.
41. Kaufmann, E.; Gose, J.; Schleyer, P. v. R. Organometalllcs 1989, 8, 2577.
42. Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1992, 114, 2112.
43. Lappert, M. F.; Slade, M. J.; Singh, A.; Atwood, J. L.; Rogers, R. D.; Shakir, R. J. Am. Chem. Soc. 1983, 105, 302.
44. Grotjahn, D. B.; Pesch, T. C.; Brewster, M. A.; Ziurys, L. M. J. Am. Chem. Soc. 2000, 122, 4735.
45. Jensen, F. Introduction to Computational Chemistry; Wiley: New York, 1999.
46. Andrews, L. J. Chem. Phys. 1967, 47, 4834.
47. Graham, G. D.; Marynick, D. S.; Lipscomb, W. N. J. Am. Chem. Soc. 1980, 102, 4572.
48. (a) Mulliken, R. S. J. Chem. Phys. 1939, 7, 339.
49. (b) Radom, L. In Molecular Structure and Conformation; Csizmadia, I. G., Ed.; Elsevier: New York, 1982; pp 1-64.
50. McKee, M. L.; Bühl, M.; Charkin, O. P.; Schleyer, P. v. R. Inorg. Chem. 1993, 32, 4549.
51. (a) Ruhlandt-Senge, K.; Ellison, J. J.; Wehmschulte, R. J.; Pauer, F.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11353.
52. (b) Pepels, A.; Günther, H.; Amoureux, J.-P.; Fernandéz, C. J. Am. Chem. Soc. 2000, 122, 9858.