Theoretical design of doubly bonded hypervalent atoms

Organometallics

Volumn 26, Issue 23, 2007, Pages 5543-5547

  Kameyama, Hiroaki ^a   Naruse, Yuji ^a   Inagaki, Satoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CHEMICAL BONDS; MOLECULAR STRUCTURE; THERMODYNAMICS;

BICYCLIC MOLECULES; DOUBLY BONDED HYPERVALENT ATOMS; DOUBLY BONDED PNICTOGEN ATOMS; MONOCYCLIC MOLECULES;

MOLECULAR DYNAMICS;

EID: 36249032112     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0700415     Document Type: Article

References (45)

1. (a) Pauling, L. The Nature of the Chemical Bond, 3rd ed., Cornell Univ. Press: Ithaca, NY, 1960.
2. (b) Gillespie. R. J. Molecular Geometry; Van Nostrand Reinhold: London. 1972.
3. (c) Block, E. Heteroatom Chemistry; VCH: New York, 1990.
4. (d) Akiba, K.-y. Chemistry of Hypervalent Compounds; Wiley-VCH: New York, 1999.
5. (a) Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
6. (b) Reed, A. E.; Schleyer, P. V. R. J. Am. Chem. Soc. 1990, 772, 1434.
7. Burggraf, L. W.; Davis, L. P. Chemically Modified Surfaces; Gordon and Breach Science: New York. 1986; pp 157-187.
8. (a) Yoshifuji, M.; Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1981, 103, 4587.
9. (b) West, R.; Fink, M. J.; Michl, J. Science 1981, 214, 2140.
10. MO bonds are as long as one another.
11. Recently, Kawashima reported molecules that connect two hypervalent silicon atoms bridged by (thio)carboxylato ligands; see: (a) Kano, N.; Nakagawa, N.; Kawashima, T. Angew. Chem., Int. Ed. 2001, 40, 3450.
12. (b) Kano, N.; Nakagawa, N.; Shinozaki. Y.; Kawashima, T.; Sato, Y.; Naruse, Y.; Inagaki, S. Organometallics 2006, 24, 2823. See also ref 17g.
13. Simon, D.; Häberle, K.; Dräger, M. J. Organomet. Chem. 1984, 267, 133.
14. (a) Bangoli, G.; Clemente, D. A. J. Chem. Soc., Chem. Commun. 1971, 311.
15. (b) Faggiani, R.; Johnson, J. P.; Brown, I. D.; Birchall, T. Acta Crystallogr. 1978, B34, 3742.
16. (c) Faggiani, R.; Johnson, J. P.; Brown, I. D.; Birchell, T. Acta Crystallogr. 1979, B35, 1227.
17. (d) Birchall, T.; Johnson, J. P. Can. J. Chem. 1982, 60, 934.
18. Gaussian 98, Revision A. 11. 3; Gaussian, Inc.: Pittsburgh, PA, 2002.
19. (a) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876.
20. (b) Ma, J.; Hozaki, A.; Inagaki, S. Phosphorus, Sulfur Silicon 2002, 177, 1705.
21. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445.
22. Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724.
23. ‡ and ΔH values (see the Supporting Information).
24. (a) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234.
25. (b) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144.
26. (c) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706.
27. (d) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5954.
28. For the bond model analysis, see (a) Inagaki, S.; Ikeda, H. J. Org. Chem. 1998, 63, 7820.
29. (b) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781. For another method of the bond model analysis, see:
30. (c) Ikeda, H.; Inagaki, S. J. Phys. Chem. A 2001, 47, 10711.
31. Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977.
32. ij are the elements of the density, Fock, and core Hamiltonian matrices of the bond orbitais, respectively. For its application, see: (a) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145.
33. (b) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893.
34. (c) Ikeda, H.; Naruse, Y.; Inagaki, S. Chem. Lett. 1999, 363.
35. (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245.
36. (e) Ikeda, H.; Ushioda, N.; Inagaki, S. Chem. Lett. 2001, 166.
37. (f) Ikeda, H.; Kato, T.; Inagaki, S. Chem. Lett. 2001, 270.
38. (g) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759.
39. (h) Naruse, Y.; Sugiura, M.; Inagaki, S. Phosphorus, Sulfur, Silicon 2003, 178, 2447.
40. (i) Otani, Y.; Nagae, O.; Naruse, Y.; Inagaki, S.; Ohno, M.; Yamaguvchi, K.; Yamamoto, G.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2003, 125, 15191.
41. (j) Naruse, Y.; Hayashi, Y.; Inagaki, S. Tetrahedron Lett. 2003, 44, 8509.
42. (k) Yasui, M.; Naruse, Y.; Inagaki, S. J. Org. Chem. 2004, 69, 7246.
43. (l) Naruse, Y.; Suzuki, T.; Inagaki, S. Tetrahedron Lett. 2005, 46, 6937.
44. (m) Naruse, Y.; Ma, J.; Takeuchi, K.; Nohara, T.; Inagaki, S. Tetrahedron 2006, 62, 4491.
45. (n) Naruse, Y.; Fukasawa, S.; Ota, S.; Deki, A.; Inagaki, S. Tetrahedron Lett. 2007, 48, 817.