Toward solution-state structure. A 6Li,1H HOESY NMR, x-ray diffraction, semiempirical (PM3, MNDO), and ab initio computational study of a chiral lithium amide

Journal of the American Chemical Society

Volumn 120, Issue 32, 1998, Pages 8143-8149

  Hilmersson, Göran ^a   Arvidsson, Per I ^a   Davidsson, Öjvind ^a   Håkansson, Mikael ^b  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM (2 METHOXY 1 PHENYLETHYL)( 1 PHENYLETHYL)AMIDE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; METAL BINDING; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 0032547251     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9724708     Document Type: Article

References (65)

1. (a) Setzer, W.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353.
2. (b) Olsher, U.; Izatt, R. M.; Bradshaw, J. S.; Dalley, K. N. Chem. Rev. 1991, 91, 137.
3. (c) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167.
4. (d) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47.
5. (a) Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M. J. J. Am. Chem. Soc. 1980, 102, 3345.
6. (b) Seebach, D.; Massig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
7. (c) Günther, H.; Moskau, D.; Bast, P.; Schmalz, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1212.
8. (d) Bauer, W.; Schleyer, P. v. R. Adv. Carbanion Chem. 1992, 1, 89.
9. (e) Moskau, D.; Brauers, F.; Günther, H.; Maercker, A. J. Am. Chem. Soc. 1987, 109, 5532.
10. (f) Gilchrist, J. H.; Harrison, A. T.; Fuller, D. J.; Collum, D. B. Magn. Reson. Chem. 1992, 30, 855.
11. (g) Mons, H.-E.; Günther, H.; Maercker, A. Chem. Ber. 1993, 126, 2747.
12. (h) Günther, H.; Moskau, D.; Dujardin, R.; Maercker, A. Tetrahedron Lett. 1986, 2251.
13. (i) Bauer, W.; Flegel, M.; Müller, G.; Schleyer, P. v. R. J. Am. Chem. Soc. 1988, 110, 6033.
14. (j) Hilmersson, G.; Davidsson, Ö. J. Organomet. Chem. 1995, 489, 175.
15. (k) Hilmersson, G.; Davidsson, Ö. Organometallics 1995, 14, 912.
16. (l) Eppers, O.; Günther, H.; Klein, K.-D.; Maercker, A. Magn. Reson. Chem. 1991, 29, 1065.
17. (m) Bauer, W. Magn. Reson. Chem. 1996, 34, 532.
18. (n) Brière, K.; Dettman, H. D.; Detellier, C. J. Magn. Reson. 1991, 94, 600.
19. (o) Balzer, H.; Berger, S. Chem. Ber. 1992, 125, 733.
20. Bauer, W.; Schleyer, P. v. R. Magn. Reson. Chem. 1988, 26, 827.
21. (a) Bauer, W.; Clark, T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1987, 109, 970.
22. (b) Bauer, W.; Hampel, F. J. Chem. Soc., Chem. Commun. 1992, 903.
23. Berger, S.; Müller, F. Chem. Ber. 1995, 128, 794.
24. Bauer, W. J. Chem. Soc., Chem. Commun. 1992, 903.
25. Avent, A.; Eaborn, C.; El-Kheli, M.; Molla, M.; Smith, D.; Sullivan, A. J. Am. Chem. Soc. 1986, 108, 3854.
26. For a typical case where the intensity error is ±20% for the large peaks and ±100% for the small peaks, the error in distance will only be ±3% and ±20%, respectively. Thus the method of determining Li-H distances by measuring NOE buildup rates does not rely on accurate intensities but rather is quite forgiving of moderate inaccuracies.
27. (a) Sapse, A.-M.; Schleyer, P. v. R. In Lithium Chemistry: A Theoretical and Experimental Overview, John Wiley & Sons Inc.: New York, 1995.
28. (b) Lambert, C.; Schleyer, P. v. R. In Carbanionen, Houben-Weyl Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, Germany, 1993; E19d, pp 1-98.
29. (a) Pratt, L. M.; Hogen-Esch, T. E.; Khan, I. M. Tetrahedron 1995, 51, 5955.
30. (b) Pratt, L. M.; Khan, I. M. J. Comput. Chem. 1995, 16, 1067.
31. (c) Pratt, L. M.; Khan, I. M. Tetrahedron: Asymmetry 1995, 6, 2165.
32. (a) Koch, R.; Wiedel, B.; Anders, E. J. Org. Chem. 1996, 61, 2523.
33. (b) Opitz, A.; Koch, R.; Katritzky, A. R.; Fan, W.-Q.; Anders, E. J. Org. Chem. 1995, 60, 3743.
34. (a) Eleveld, M. B.; Hogeveen, H. Tetrahedron Lett. 1984, 25, 5187.
35. (b) Overberger, C. G.; Marullo, N. P.; Hiskey, R. G. J. Am. Chem. Soc. 1961, 83, 1374.
36. Hilmersson, G.; Davidsson, O. J. Org. Chem. 1995, 60, 7660.
37. (a) Barr, D.; Doyle, M. J.; Mulvey, R. E.; Raithby, P. R.; Reed, D.; Snaith, R.; Wright, D. S. J. Chem. Soc., Chem. Commun. 1989, 318.
38. (b) Reich, H. J.; Green, D. P. J. Am. Chem. Soc. 1989, 111, 8729.
39. (c) Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1382.
40. (d) Boche, G.; Fraenkel, G.; Cabral, J.; Harms, K.; van Eikema Hommes, N. J. R.; Lohrenz, J.; Marsch, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1992, 114, 1562.
41. (e) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009.
42. (f) Collum, D. B.; Lucht, B. L. J. Am. Chem. Soc. 1995, 117, 9863.
43. (g) Reich, H. J.; Kulicke, K. J. J. Am. Chem. Soc. 1996, 118, 273.
44. (h) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 3529.
45. (i) Hilmersson, G.; Ahlberg, P.; Davidsson, Ö. J. Am. Chem. Soc. 1996, 118, 3539.
46. Hilmersson, G.; Arvidsson, P. I.; Davidsson, Ö.; Håkansson, M. Organometallics 1997, 16, 3352.
47. The QUEST 3D and VISTA 2.0 program packages were used for data searching and evaluation of the CSD.
48. Israelachvili, J. Intermolecular surface forces, 2nd ed.; Academic Press: London, 1991; p 124.
49. Glaser, R.; Streitwieser, A. Theochem 1988, 163, 19.
50. Engdahl, C.; Ahlberg, P. J. Am. Chem. Soc. 1979, 101, 3940.
51. (a) Roberts, G. C. K. NMR of Macromolecules-A practical Approach: IRL Press: Oxford, U.K., 1993.
52. (b) Neuhaus, D.; Williamson, M. P. The Nuclear Querhauser Effect in Structural and Conformational Analysis; VCH Publishers Inc.; New York, 1989.
53. (c) Sette, M.; Ropp, J. S.; Hernandez, G.; La Mar, G. N. J. Am. Chem. Soc. 1993, 115, 5237.
54. PM3: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209. Li parameters: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301.
55. PM3: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209. Li parameters: Anders, E.; Koch, R.; Freunscht, P. J. Comput. Chem. 1993, 14, 1301.
56. MNDO: Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899. parameters: Thiel, W.; Clark, T. QCPE 438. QCPE Bull. 1982, 2, 36.
57. MNDO: Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899. Li parameters: Thiel, W.; Clark, T. QCPE 438. QCPE Bull. 1982, 2, 36.
58. Hehre, W. J.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1969, 2657.
59. Spartan version 4.1, Wavetunction Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715.
60. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
61. Gaussian 94 (Revision B.3): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R. Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K. Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B. Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1995.
62. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939.
63. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
64. Spitznagel, G. W.; Clark, T.; Chandrasekhar, J.; Schleyer, P. v. R. J. Comput. Chem. 1982, 3, 363.
65. Frequencies for 5·THF were not calculated at the HF/6-31G(d) level of theory.