Intramolecular non-bonded interaction between selenium and oxygen as revealed by 17O and 77Se NMR spectroscopy and natural bond orbital analysis

Chemical Communications

Volumn , Issue 2, 1999, Pages 205-206

  Komatsu, Hiroto ^a   Iwaoka, Michio ^a   Tomoda, Shuji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (FORMYLMETHYL)BENZENESELENENYL DERIVATIVE; 2 (HYDROXYMETHYL)BENZENESELENENYL DERIVATIVE; ORGANOSELENIUM DERIVATIVE; OXYGEN; SELENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; MEASUREMENT; NATURAL BOND ORBITAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0033590570     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808126c     Document Type: Article

References (26)

1. K. Fujita, M. Iwaoka and S. Tomoda, Chem. Lett., 1994, 923; K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, Tetrahedron, 1997, 53, 2029; T. Wirth, Liebigs Ann./Recueil, 1997, 2189.
2. K. Fujita, M. Iwaoka and S. Tomoda, Chem. Lett., 1994, 923; K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, Tetrahedron, 1997, 53, 2029; T. Wirth, Liebigs Ann./Recueil, 1997, 2189.
3. K. Fujita, M. Iwaoka and S. Tomoda, Chem. Lett., 1994, 923; K. Fujita, K. Murata, M. Iwaoka and S. Tomoda, Tetrahedron, 1997, 53, 2029; T. Wirth, Liebigs Ann./Recueil, 1997, 2189.
4. M. Iwaoka and S. Tomoda, J. Chem. SM, Chem. Commun., 1992, 1165; M. Iwaoku and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557; R. Kaur, H. B. Singh and R. P. Patel. J Chem. Soc, Dalton Trans., 1996, 2719; T. Wirth, S. Häuptli and M. Leuenberger. Tetrahedron: Asymmetry, 1998, 9, 547.
5. M. Iwaoka and S. Tomoda, J. Chem. SM, Chem. Commun., 1992, 1165; M. Iwaoku and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557; R. Kaur, H. B. Singh and R. P. Patel. J Chem. Soc, Dalton Trans., 1996, 2719; T. Wirth, S. Häuptli and M. Leuenberger. Tetrahedron: Asymmetry, 1998, 9, 547.
6. M. Iwaoka and S. Tomoda, J. Chem. SM, Chem. Commun., 1992, 1165; M. Iwaoku and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557; R. Kaur, H. B. Singh and R. P. Patel. J Chem. Soc, Dalton Trans., 1996, 2719; T. Wirth, S. Häuptli and M. Leuenberger. Tetrahedron: Asymmetry, 1998, 9, 547.
7. M. Iwaoka and S. Tomoda, J. Chem. SM, Chem. Commun., 1992, 1165; M. Iwaoku and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557; R. Kaur, H. B. Singh and R. P. Patel. J Chem. Soc, Dalton Trans., 1996, 2719; T. Wirth, S. Häuptli and M. Leuenberger. Tetrahedron: Asymmetry, 1998, 9, 547.
8. M. Iwaoka and S. Tomoda, J. Am. Chem. Soc., 1996, 118, 8077.
9. M. Iwaoka, H. Komatsu and S. Tomoda, Chem. Lett., 1998, 969.
10. L. C. Allen, J. Am. Chem. Soc., 1989, 111, 9003.
11. B. M. Goldstein, S. D. Kennedy and W. J. Hennen, J. Am. Chem. Soc., 1990, 112, 8265; F. T. Burling and B. M. Goldstein, J. Am. Chem. Soc., 1992, 114, 2313; D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh and J. Reihenspies, J. Am. Chem. Soc., 1993, 115, 5056.
12. B. M. Goldstein, S. D. Kennedy and W. J. Hennen, J. Am. Chem. Soc., 1990, 112, 8265; F. T. Burling and B. M. Goldstein, J. Am. Chem. Soc., 1992, 114, 2313; D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh and J. Reihenspies, J. Am. Chem. Soc., 1993, 115, 5056.
13. B. M. Goldstein, S. D. Kennedy and W. J. Hennen, J. Am. Chem. Soc., 1990, 112, 8265; F. T. Burling and B. M. Goldstein, J. Am. Chem. Soc., 1992, 114, 2313; D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh and J. Reihenspies, J. Am. Chem. Soc., 1993, 115, 5056.
14. A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066; A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735; A. E. Reed and F. Weinhold, J. Chem. Phys., 1985, 83, 1736; A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
15. A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066; A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735; A. E. Reed and F. Weinhold, J. Chem. Phys., 1985, 83, 1736; A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
16. A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066; A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735; A. E. Reed and F. Weinhold, J. Chem. Phys., 1985, 83, 1736; A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
17. A. E. Reed and F. Weinhold, J. Chem. Phys., 1983, 78, 4066; A. E. Reed, R. B. Weinstock and F. Weinhold, J. Chem. Phys., 1985, 83, 735; A. E. Reed and F. Weinhold, J. Chem. Phys., 1985, 83, 1736; A. E. Reed, L. A. Curtiss and F. Weinhold, Chem. Rev., 1988, 88, 899.
18. 13C, 17O and 77Se N1MR spectra, la-c, If15 and 2eu are known compounds.
19. 17O NMR Spectroscopy in Organic Chemistry, ed. D. W. Boykin, CRC Press, Florida, 1991, p. 205.
20. P. Balakrishnan, A. L. Baumstark and D. W. Boykin, Tetrahedron Lett., 1984. 169.
21. M.-T. Béraldin, E. Vauihier and S. Fliszâr, Can. /. Chem., 1982, 60, 106; G. Jaccard, P.-A. Carrupt and J. Lauterwein, Magn. Resan. Chem., 1988, 26. 239.
22. M.-T. Béraldin, E. Vauihier and S. Fliszâr, Can. /. Chem., 1982, 60, 106; G. Jaccard, P.-A. Carrupt and J. Lauterwein, Magn. Resan. Chem., 1988, 26. 239.
23. Gaassian 94 was used for all calculations performed in this paper: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M A. Robb, J. R. Cheeseman, T. A. Keilh, 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. Nanayakkara, M. Challacombe, C. Y. Pong, 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.
24. Gaussian Basis Sets for Molecular Calculations, ed. S. Huzinaga. Elsevier, Amsterdam, 1984.
25. M. Iwaoka and S. Tomoda, Phosphorus Sulfur Silicon Relal. Ele., 1992, 67, 125.
26. G. Llabrès, M. Baiwir, J.-L. Pielte and L. Christiaens, Org. Magn. Reson 7., 1981, 15, 152.