Reactions of H2X=XH2 and H2X=O Double Bonds (X = Si, Ge, Sn, Pb): Are 1,3-Dioxa-2,4-dimetaletanes Unusual Molecules?

Inorganic Chemistry

Volumn 36, Issue 19, 1997, Pages 4241-4246

  Kapp, Jürgen ^b   Remko, Milan ^a   Schleyer, Paul V R ^b  

^a Faculty of Natural Sciences   (Slovakia)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000189142     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic961519s     Document Type: Article

References (65)

1. (a) Raabe, G.; Michl, J. Chem. Rev. 1985, 85, 419.
2. (b) Brook, A. G.; Baines, K. M. Adv. Organomet. Chem. 1986, 25, 1.
3. (c) West, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 1201.
4. (d) Tsumuraya, T.; Batcheller, S. A.; Masamune, A. Angew. Chem., Int. Ed. Engl. 1991, 30, 902.
5. (a) Trinquier, G.; Barthelat, J. C.; Satgé, J. J. Am. Chem. Soc. 1982, 104, 5931.
6. (b) Goldberg, D. E.; Hitchcock, P. B.; Lappert, M. F.; Thomas, K. M.; Thorne, A. J.; Fjeldberg, T.; Haaland, A.; Schilling, B. E. R. J. Chem. Soc., Dalton Trans. 1986, 2387.
7. (c) Grev, R. S. Adv. Organomet. Chem. 1991, 33, 125.
8. (d) Jacobsen, H.; Ziegler, T. J. Am. Chem. Soc. 1994, 116, 3667.
9. For recent reviews see: (a) Sekiguchi, A.; Sakurai, H. Adv. Organomet. Chem. 1995, 37, 1. (b) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
10. For recent reviews see: (a) Sekiguchi, A.; Sakurai, H. Adv. Organomet. Chem. 1995, 37, 1. (b) Driess, M.; Grützmacher, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 828.
11. Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds. Comprehensive Organometallic Chemistry II; Elsevier: Oxford, U.K., 1995; Vol. 2.
12. (a) Barrau, J.; Escudié, J.; Satgé, J. Chem. Rev. 1990, 90, 283.
13. (b) Escudié, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. Coord. Chem. Rev. 1994, 130, 427.
14. (c) Masamune, S.; Batcheller, S. A.; Park, J.; Davis, W. M. J. Am. Chem. Soc. 1989, 111, 1888.
15. Elscnenbroich C.; Salzer, A. Organometallics-A Concise Introduction; VCH: Weinheim, Germany, 1989; pp 95-146.
16. Kropf, H., Schaumann, E., Eds. Methoden der Organische Chemie (Houben-Weil); G. Thieme Verlag: Stuttgart, Germany, 1993; Vol. E15.
17. Kutzelnigg, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 272.
18. Kapp, J.; Remko, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1996, 118, 5745.
19. (a) Luke, B. T.; Pople, J. A.; Krogh-Jespersen, M.-B.; Apeloig, Y.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 260.
20. (b) Schleyer, P. v. R.; Kost, D. J. Am. Chem. Soc. 1988, 110, 2105.
21. Epiotis, N. D. Unified Valence Bond Theory of Electronic Structure; Springer Verlag: Berlin, 1982.
22. West, R.; Yokelson, H. B.; Gillette, G. R.; Millevolte, A. J. In Silicon Chemistry; Corey, E. R., Corey, J. Y., Gaspar, P. P., Eds.; Ellis Horwood Ltd.: Chichester, U.K., 1988; pp 269-281.
23. Edelman, M. A.; Hitchcock, P. B.; Lappert, M. F. J. Chem. Soc., Chem. Commun. 1990, 1116.
24. Streitwieser, A., Jr.; Heathcock, C. H. Introduction to Organic Chemistry; Macmillan Publishing: New York, 1986.
25. Kudo, T.; Nagase, S. J. Am. Chem. Soc. 1985, 107, 2589.
26. Fink, M. J.; Haller, K. J.; West, R.; Michl, J. J. Am. Chem. Soc. 1984, 106, 822.
27. Yokelson, H. B.; Millevolte, A. J.; Adams, B. R.; West, R. J. Am. Chem. Soc. 1987, 109, 4116.
28. 2-X π complexes, see: Cremer, D.; Gauss, J.; Cremer, E. J. Mol. Struct. 1988, 169, 531.
29. 2-X π complexes, see: Cremer, D.; Gauss, J.; Cremer, E. J. Mol. Struct. 1988, 169, 531.
30. (a) Nagase, S.; Kudo, T. Organometallics 1988, 7, 2534.
31. (b) Nagase, S.; Kudo, T.; Kurakake, T. J. Chem. Soc., Chem. Commun. 1988, 1063.
32. (c) Nagase, S. Acc. Chem. Res. 1995, 28, 469.
33. Nagase, S. Polyhedron 1991, 10, 1299.
34. (a) Nguyen, K. A.; Caroll, M. T.; Gordon, M. S. J. Am. Chem. Soc. 1991, 113, 7924.
35. (b) Boatz, J. A.; Gordon, M. S. J. Phys. Chem. 1989, 93, 3025.
36. 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.; Gonzalez, C.; Pople, J. A. GAUSSIAN94; Gaussian, Inc.: Pittsburgh, PA, 1995.
37. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098.
38. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
39. Hehre, W. J.; Radom, L.; Schleyer, P. v. R; Pople, J. A: Ab Initio Molecular Orbital Theory; J. Wiley & Sons: New York, 1986.
40. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
41. d-Polarization Functions from: Huzinaga, S., Ed. Gaussian Basis Sets for Molecular Calculations; Elsevier: New York, 1984.
42. Küchle, W.; Dolg, M.; Stoll, H.; Preuss, H. Mol. Phys. 1991, 74, 1245.
43. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
44. (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
45. (c) Reed, A. E.; Curtis, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
46. Masamune, S. In Silicon Chemistry, Corey, E. R., Corey, J. Y., Gaspar, P. P., Eds.; Ellis Horwood Ltd.: Chichester, U.K., 1988; pp 257-268.
47. 2 species see: Balasubramanian, K. J. Chem. Phys. 1988, 89, 5731.
48. (a) Trinquier, G. J. Am. Chem. Soc. 1990, 112, 2130.
49. (b) Trinquier, G. J. Am. Chem. Soc. 1991, 113, 144.
50. Ross, R. B.; Powers, J. M.; Atashroo, T.; Ermler, W. C.; LaJohn, L. A.; Christiansen, P. A. J. Chem. Phys. 1990, 93, 6654.
51. Reference 4, pp 314-315.
52. Trinquier, G.; Barthelat, J.-C. J. Am. Chem. Soc. 1990, 112, 9121.
53. Kaupp, M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1993, 115, 1061.
54. (a) Nagase, S.; Nakano, M.; Kudo, T. J. Chem. Soc., Chem. Commun. 1987, 60.
55. (b) Nagase, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 329.
56. 2XO group: -12.62 (C), -18.48 (Si), -12.89 (Ge), -13.96 (Sn) -14.86 ("nonrelativistic" Pb), -9.65 (Pb), in kcal/mol (at Becke3LYP/ DZ+P incl. ZPE, from ref 9).
57. 2 rings of the other group 14 elements (kcal/mol): 86.54 (C), 90.41 (Si), 19.32 (Ge), -2.20 (Sn), 4.38 ("nonrelativistic" Pb).
58. 2 complexes in au and kcal/mol: -45.59840, 37.37 (C), -42.30626, 29.43 (Si), -42.18405, 27.06 (Ge), -41.35243, 25.16 (Sn), -40.86048, 24.39 ("nonrelativistic" Pb), -41.43891, 24.11 (Pb).
59. (a) Teramae, H. J. Am. Chem. Soc. 1987, 109, 4140.
60. 3d symmetric structures: Nagase, S.; Kobayashi, K.; Kudo, T. Main Group Met. Chem. 1994, 17, 171. See also ref 20.
61. 2h) at CASSCF(4,4)/DZ+P to evaluate the amount of singlet biradical character. The calculation gave 88.1%, supporting our description of the diplumbene molecule. See also: (a) Fukutome, H. Int. J. Quantum Chem. 1981, 20, 955. (b) Seeger, R.; Pople, J. A. J. Chem. Phys. 1977, 66, 3045. Yamaguchi, K. Theochem 1983, 103, 101.
62. 2h) at CASSCF(4,4)/DZ+P to evaluate the amount of singlet biradical character. The calculation gave 88.1%, supporting our description of the diplumbene molecule. See also: (a) Fukutome, H. Int. J. Quantum Chem. 1981, 20, 955. (b) Seeger, R.; Pople, J. A. J. Chem. Phys. 1977, 66, 3045. Yamaguchi, K. Theochem 1983, 103, 101.
63. 2h) at CASSCF(4,4)/DZ+P to evaluate the amount of singlet biradical character. The calculation gave 88.1%, supporting our description of the diplumbene molecule. See also: (a) Fukutome, H. Int. J. Quantum Chem. 1981, 20, 955. (b) Seeger, R.; Pople, J. A. J. Chem. Phys. 1977, 66, 3045. Yamaguchi, K. Theochem 1983, 103, 101.
64. Windus, T. L.; Gordon, M. S. J. Am. Chem. Soc. 1992, 114, 9559.
65. 4 geometry). However, spin-orbit coupling in open-shell species may affect the relative energies.