Theoretical investigation on the conformational preferences of sulfinimines

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 1, 2000, Pages 43-50

  Bharatam, Prasad V ^a   Uppal, Punam ^a   Kaur, Amita ^a   Kaur, Damanjit ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CHEMICAL BONDS; CONFORMATIONS; ELECTRONS; MOLECULAR STRUCTURE; NITROGEN; OPTIMIZATION; OXYGEN; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; SULFUR; SURFACES;

DENSITY FUNCTIONAL METHODS; HYPERCONJUGATION; POTENTIAL ENERGY SURFACES; REPULSIVE INTERACTIONS; SULFINIMINES; SYNPERIPLANAR ARRANGEMENT;

AMINES;

EID: 0033993072     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907865g     Document Type: Article

References (69)

1. (a) F. A. Davis, A. J. Friedman and E. W. Kluger, J. Am. Chem. Soc., 1974, 96, 5000
2. (b) F. A. Davis, A. J. Friedman and U. K. Nadir, J. Am. Chem. Soc., 1978, 100, 2844.
3. F. A. Davis, R. E. Reddy, J. M. Szewczyk, G. V. Reddy, P. S. Portonova, H. Zhang, D. Fanelli, R. T. Reddy, P. Zhou and P. J. Carrol, J. Org. Chem., 1997, 62, 2555, supplementary material and refs. therein.
4. (a) R. Annunziata, M. Cinquini and F. Cozzi, J. Chem. Soc., Perkin Trans. 1, 1982, 339
5. (b) D. H. Hua, S. W. Miao, J. S. Chen and S. Iguchi, J. Org. Chem., 1991, 56, 4
6. (c) D. R. J. Hose, M. F. Hahon, K. C. Molloy, T. Raynham and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1996, 691
7. (d) T.-K. Yang, R.-Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi and T.-T. Jong, J. Org. Chem., 1994, 59, 914.
8. F. A. Davis, P. Zhou and B.-C. Chen, Chem. Soc. Rev., 1998, 27, 13 and refs. therein.
9. (a) A. Viso, R. F. de la Pradilla, C. Guerrero-Strachan, M. Alonosa, M. Martinez-Ripoll and I. Andre, J. Org. Chem., 1997, 62, 2316 and refs. therein
10. (b) K. Burger, J. Albanbauer, F. Kafig and S. S. Penninger, Liebigs Ann. Chem., 1977, 624
11. (c) T. Yoshida, S. Naruto, H. Uno and H. Nishimura, Chem. Pharm. Bull., 1982, 30, 2820
12. (d) M. Cinquini and F. Cozzi, J. Chem. Soc., Chem. Commun., 1977, 723.
13. J. L. G. Ruano, I. Fernandez, M. d. P. Catalina and A. A. Cruz, Tetrahedron: Asymmetry, 1996, 7, 3407
14. J. L. G. Ruano, I. Fernandez and C. Hamdouchi, Tetrahedron Lett., 1995, 36, 295
15. F. A. Davis, G. V. Reddy and H. Liu, J. Am. Chem. Soc., 1995, 117, 3651
16. F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243
17. F. A. Davis and P. Zhou, Tetrahedron Lett., 1994, 35, 7525
18. F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511
19. F. A. Davis and G. V. Reddy, Tetrahedron Lett., 1996, 37, 4349
20. F. A. Davis, H. Liu and G. V. Reddy, Tetrahedron Lett., 1996, 37, 5473.
21. For leading references on the chemistry of sulfenic acids see: F. A. Davis, L. A. Jenkins and R. L. Billimers, J. Org. Chem., 1986, 51, 1033.
22. F. A. Davis, R. E. Reddy and J. M. Szewczyk, J. Org. Chem., 1995, 60, 7037.
23. For leading references on the synthesis of amino acids using sulfinimines see refs. 3(b), 4, 8 also ref. 11 below and F. A. Davis, P. S. Portonova, R. E. Reddy and Y.-H. Chiu, J. Org. Chem., 1996, 61, 440
24. J. Jiang, K. Schumacher, M. M. Joullie, F. A. Davis and R. E. Reddy, Tetrahedron Lett., 1994, 35, 2121
25. F. A. Davis, J. Szewczyk and R. E. Reddy, J. Org. Chem., 1996, 61, 2222
26. T. Fujisawa, Y. Kooriyama and M. Shimizu, Tetrahedron Lett., 1996, 37, 3881
27. F. A. Davis and R. E. Reddy, Tetrahedron: Asymmetry, 1994, 5, 955.
28. M. Mikalajczyk, P. Lyzwa, J. Drabowicz, M. W. Wieczorek and J. Blaszczyk, Chem. Commun., 1996, 1503
29. I. M. Lefebvre and S. A. Evans, J. Org. Chem., 1997, 62, 7532.
30. F. A. Davis, T. R. Reddy and R. E. Reddy, J. Org. Chem., 1992, 57, 6387.
31. T. Balasubramanian and A. Hassner, J. Org. Chem., 1996, 37, 5755.
32. (a) F. A. Davis, J. M. Kaminski, E. W. Kluger and H. S. Freilich, J. Am. Chem. Soc., 1975, 97, 7085
33. (b) F. A. Davis and E. W. Kluger, J. Am. Chem. Soc., 1976, 98, 302.
34. A. E. Reed and P. v. R. Schleyer, J. Am. Chem. Soc., 1987, 109, 7362
35. A. E. Reed and P. v. R. Schleyer, Inorg. Chem., 1988, 27, 3696
36. A. E. Reed and P. v. R. Schleyer, J. Am. Chem. Soc., 1990, 112, 1434.
37. -1 at HF/6-31 + G* and MP2/6-31 + G*//HF/6-31 + G* levels respectively;
38. (b) K. Lammertsma and B. V. Prasad, J. Am. Chem. Soc., 1994, 116, 642
39. (c) B. V. Prasad, P. Uppal and P. S. Bassi, Chem. Phys. Lett., 1997, 276, 31
40. (d) B. V. Prasad, G. Grover, P. Uppal and D. Kaur, J. Mol. Struct. (THEOCHEM), 1999, 458, 227
41. (e) B. V. Prasad, P. Uppal and D. Kaur, unpublished results
42. (f) B. V. Prasad, S. Kumar and M. P. Mahajan, Tetrahedron, 1998, submitted for publication.
43. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley-Interscience, New York, 1986
44. J. B. Foresman and E. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, 2nd edn., 1996.
45. R. G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989
46. L. J. Bartolotti and K. Fluchick, in Reviews in Computational Chemistry, vol. 7, eds. K. B. Lipkowitz and D. B. Boyd, VCH, New York, 1996, pp. 187-216.
47. 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, 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, 1995.
48. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213.
49. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 5648
50. (b) A. D. Becke, Phys. Rev. A, 1988, 38, 3098
51. (c) C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1980, 37, 785
52. (d) S. H. Vosko, L. Wilk and M. Nusair, Can. J. Phys., 1980, 58, 1200.
53. J. S. Binkley and J. A. Pople, Int. J. Quantum Chem., 1975, 9, 229
54. J. A. Pople and J. S. Binkley, Int. J. Quantum Chem. Symp., 1976, 10, 1.
55. A. P. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16502.
56. A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735
57. A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
58. M. J. S. Dewar, E. G. Zoebisch and E. F. Healy, J. Am. Chem. Soc., 1985, 107, 3902.
59. MOPAC semi-empirical package obtained from Quantum Chemistry Program Exchange (QCPE No. 455), Indiana University, Bloomington, IN.
60. P. D. Robinson, D. H. Hua, J. S. Chen and S. Saha, Acta Crystallogr., Sect. C, 1991, 47, 594.
61. G. Böttger, A. Geisler, R. Fröhlich and E.-U. Würthwein, J. Org. Chem., 1997, 62, 6407.
62. G. H. Whitham, Organosulfur Chemistry, Oxford Science Publications, Oxford, 1995.
63. Using complete optimizations at MP2/6-31 + G* level 1r3 and 1tsr3 could not be located on the PE surface. All attempts to locate these structures using the Eigenvalue Following (EF) procedures also failed to find them. Finally as shown in Fig. 2, partial optimization with constrained CNSO dihedral angles also failed to show any minimum corresponding to 1r3.
64. (a) J. L. Radkiewicz, M. A. Michael, E. Goldstein and K. N. Houk, J. Org. Chem., 1998, 63, 1419
65. (b) S. Lacombe, M. Loudet, A. Dargelos and E. Robert-Banchereau, J. Org. Chem., 1998, 63, 2281.
66. The calculations at HF/6-31 + G*, B3LYP/6-31 + G* and MP2/6-31 + G* levels did not lead to any such stationary point. This may be a limitation of the optimization procedure. The important geometric parameters of 1tsi obtained at the HF/6-31 G* level are C-N 1.232, N-S 1.607, S-O 1.458 Å N-S-O 114.7°, C-N-S 180.05°, C-N-S-O 138.0° and C-N-S-H 246.9°. Normal mode analysis of the negative frequency of 1tsi (at HF/6-31 G* level) and 2tsi (at HF/6-31 G* level) showed vibration corresponding to N-inversion and C=N rotation.
67. The structural features of 2tsi do appear to connect 2E and 2Z. We have tried to locate other possible structures of 2tsi. All other apparently possible structures converged to 2tsi on complete optimization.
68. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290.
69. R. D. Bindal, J. T. Golab and J. A. Katzenellenbogen, J. Am. Chem. Soc., 1990, 112, 7861.