Ambiphilicity of dichlorosilylene in a single molecule

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 85-88

  Ghadwal, Rajendra S ^a   Roesky, Herbert W ^a   Merkel, Sebastian ^a   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Ambiphilicity; Computational chemistry; Lewis acids; Lewis bases; Silylenes

Indexed keywords

CHARGE-DENSITY ANALYSIS; CHEMICAL EQUATIONS; DONOR ACCEPTORS; DONOR AND ACCEPTOR; DONOR BONDS; IMIDAZOL; LEWIS ACID; LEWIS BASE; LEWIS BASIS; SILYLENES; SINGLE BOND; SINGLE MOLECULE;

ACIDS; BOND LENGTH; CHEMICAL REACTIONS; SILICON;

COMPUTATIONAL CHEMISTRY;

EID: 73949120807     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902930     Document Type: Article

References (85)

1. a) K. Raghavachari, J. ChandrasekharX, M. S. Gordon, K. J. Dykema, J. Am. Chem. Soc. 1984, 106, 5853-5859;
2. b) G. Trinquier, J.-P. Malrieu, J. Am. Chem. Soc. 1987, 109, 5303-5315;
3. c) T. P. Hamilton, H. F. Schaefer III, J. Chem. Phys. 1989, 90, 1031-1035;
4. d) N. Auner, J. Grobe, T. Müller, H. W. Rathmann, Organometallics 2000, 19, 3476-3485;
5. e) Y. Apeloig, S. Sklenak, Can. J. Chem. 2000, 78, 1496-1510;
6. f) P. V. Bharatam, R. Moudgil, D. Kaur, Organometallics 2002, 21, 3683-3690;
7. g) J. D. Larkin, H. F. Schaefer III, J. Chem. Phys. 2004, 121, 9361-9367;
8. h) J. Oláh, F. De Proft, T. Veszprémi, P. Geerlings, J. Phys. Chem. A 2005, 109, 1608-1615;
9. i) J. Oláh, T. Veszprémi, F. De Proft, P. Geerlings, J. Phys. Chem. A 2007, 111, 10815-10823.
10. a) M. Denk, R. Lennon, R. Hayashi, R. West, A. V. Belyakov, H. P. Verne, A. Haaland, M. Wagner, N. Metzler, J. Am. Chem. Soc. 1994, 116, 2691-2692;
11. b) B. Gehrhus, M. F. Lappert, J. Heinicke, R. Boese, D. Bläser, J. Chem. Soc. Chem. Commun. 1995, 1931-1932;
12. c) B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Z. Anorg. Allg. Chem. 2005, 631, 1383-1386;
13. d) M. Driess, S. Yao, M. Brym, C. van Wüllen, D. Lentz, J. Am. Chem. Soc. 2006, 128, 9628-9629;
14. e) C.-W. So, H. W. Roesky, J. Magull, R. B. Oswald, Angew. Chem. 2006, 118, 4052-4054;
15. Angew. Chem. Int. Ed. 2006, 45, 3948-3950;
16. f) C.-W. So, H. W. Roesky, P. M. Gurubasavaraj, R. B. Oswald, M. T. Garmer, P. G. Jones, S. Blaurock, J. Am. Chem. Soc. 2007, 129, 12049-12054.
17. a) N. Tokitoh, R. Okazaki, Coord. Chem. Rev. 2000, 210, 251-277;
18. b) M. Haaf, T. A. Schmedake, R. West, Acc. Chem. Res. 2000, 33, 704-714;
19. c) B. Gehrhus, M. F. Lappert, J. Organomet. Chem. 2001, 617-618, 209-223;
20. d) N. J. Hill, R. West, J. Organomet. Chem. 2004, 689, 4165-4183;
21. e) H. Ottosson, P. G. Steel, Chem. Eur. J. 2006, 12, 1576-1585;
22. f) S. Yao, M. Brym, C van Wüllen, M. Driess, Angew. Chem. 2007, 119, 4237-4240;
23. Angew. Chem. Int. Ed. 2007, 46, 4159-4162;
24. g) S. Yao, C. van Wüllen, X.-Y. Sun, M. Driess, Angew. Chem. 2008, 120, 3294-3297;
25. Angew. Chem. Int. Ed. 2008, 47, 3250-325;
26. h) S. Nagendran, H. W. Roesky, Organometallics 2008, 27, 457-492;
27. i) A. Jana, C. Schulzke, H. W. Roesky, J. Am. Chem. Soc. 2009, 131, 4600-4601;
28. j) A. C. Tomasik, A. Mitra, R. West, Organometallics 2009, 25, 378-381.
29. a) M. Denk, R. K. Hayashi, R. West, J. Chem. Soc. Chem. Commun. 1994, 33-34;
30. b) R. West, M. Denk, Pure Appl. Chem. 1996, 68, 785-788;
31. c) B. Gehrhus, P. B. Hitchcock, M. F. Lappert, H. Maciejewski, Organometallics 1998, 17, 5599-5601;
32. d) X. Cai, B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Can. J. Chem. 2000, 78, 1484-1490;
33. e) A. Meltzer, C. Präsang, C. Milsmann, M. Driess, Angew. Chem. 2009, 121, 3216-3219;
34. Angew. Chem. Int. Ed. 2009, 48, 3170-3173;
35. f) W. Yang, H. Fu, H. Wang, M. Chen, Y. Ding, H. W. Roesky, A. Jana, Inorg. Chem. 2009, 48, 5058-5060.
36. N. Metzler, M. Denk, J. Chem. Soc. Chem. Commun. 1996, 2657-2658.
37. a) R. A. Benkeser, Acc. Chem. Res. 1971, 4, 94-100;
38. b) S. H. Kang, J. S. Han, M. E. Lee, B. R. Yoo, I. N. Jung, Organometallics 2003, 22, 2551-2553.
39. a) W. Ando, K. Hagiwara, A. Sekiguchi, Organometallics 1987, 6, 2270-2271;
40. b) G. R. Gillette, G. H. Noren, R. West, Organometallics 1987, 6, 2617-2618;
41. c) C. A. Arrington, J. T. Petty, S. E. Payne, W. C. K. Haskins, J. Am. Chem. Soc. 1988, 110, 6240-6241;
42. d) M. A. Pearsall, R. West, J. Am. Chem Soc. 1988, 110, 7228-7229;
43. e) W. Ando, A. Sekiguchi, K. Hagiwara, A. Sakakibara, H. Yoshida, Organometallics 1988, 7, 558-559;
44. f) G. R. Gillette, G. H. Noren, R. West, Organometallics 1989, 8, 487-491;
45. g) G. Levin, P K. Das, C. Bilgrien, C. L. Lee, Organometallics 1989, 8, 1206-1211.
46. N. Takeda, H. Suzuki, N. Tokitoh, R. Okazaki, J. Am. Chem. Soc. 1997, 119, 1456-1457.
47. R. Waterman, P. G. Hayes, T. D. Tilley, Acc. Chem. Res. 2007, 40, 712-719, and references therein.
48. a) R. S. Ghadwal, H. W. Roesky, S. Merkel, J. Henn, D. Stalke, Angew. Chem. 2009, 121, 5793-5796;
49. Angew. Chem. Int. Ed. 2009, 48, 5683-5686;
50. b) A. C. Filippou, O. Chernov, G. Schnakenburg, Angew. Chem. 2009, 121, 5797-5800;
51. Angew. Chem. Int. Ed. 2009, 48, 5687-5690.
52. N. Takeda, T. Kajiwara, N. Tokitoh, Chem. Lett. 2001, 1076-1077.
53. M. Nanjo, K. Matsudo, M. Kurihara, S. Nakamura, Y. Sakaguchi, H. Hayashi, K. Mochida, Organometallics 2006, 25, 832-838.
54. a) N Nakata, R. Izumi, V. Ya. Lee, M. Ichinohe, A. Sekiguchi, Chem. Lett. 2005, 34, 582-583;
55. b) T. Kajiwara, N. Takeda, T. Sasamori, N. Tokitoh, J. Chem. Soc. Chem. Commun. 2004, 2218-2219.
56. N. Nakata, A. Sekiguchi, J. Am. Chem. Soc. 2005, 127, 422-423.
57. R. F. W. Bader in Atoms in Molecules, Oxford University Press, New York, 1990.
58. a) R. F. W. Bader, J. Phys. Chem. A 1998, 102, 7314-7323;
59. b) R. F. W. Bader, H. Essén, J. Chem. Phys. 1984, 80, 1943-1960;
60. c) T. S. Koritsanszky, P. Coppens, Chem. Rev. 2001, 101, 1583-1627;
61. d) C. Lecomte, M. Souhassou, S. Pillet, J. Mol. Struct. 2003, 647, 53-64;
62. e) C. Gatti, Z. Kristallogr. 2005, 220, 399-457.
63. a) P. Macchi, A. Sironi, Coord. Chem. Rev. 2003, 238-239, 383-412;
64. b) L. J. Farrugia, C. Evans, M. Tegel, J. Phys. Chem. A 2006, 110, 7952-7961;
65. c) C. Gatti, D. Lasi, Faraday Discuss. 2007, 135, 55-78;
66. d) A. Reisinger, N. Trapp, I. Krossing, S. Altmannshofer, V. Herz, M. Presnitz, W. Scherer, Angew. Chem. 2007, 119, 8445-8449;
67. Angew. Chem. Int. Ed. 2007, 46, 8295-8298;
68. e) U. Flierler, M. Burzler, D. Leusser, J. Henn, H. Ott, H. Braunschweig, D. Stalke, Angew. Chem. 2008, 120, 4393-4397;
69. Angew. Chem. Int. Ed. 2008, 47, 4321-4325;
70. f) L. J. Farrugia, C. Evans, D. Lentz, M. Roemer, J. Am. Chem. Soc. 2009, 131, 1251-1268.
71. a) T. Kottke, D. Stalke, J. Appl. Crystallogr. 1993, 26, 615-619;
72. b) D. Stalke, Chem. Soc. Rev. 1998, 27, 171-178.
73. SAINT v7.46A, Bruker AXS Inc., Madison, WI, 2007.
74. TWINABS 2008/2, G. M. Sheldrick, University of Göttingen, Göttingen, 2008.
75. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
76. a) R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165-169;
77. b) O. Treutier, R. Ahlrichs, J. Chem. Phys. 1995, 102, 346-354;
78. c) K. Eichkorn, F. Weigend, O. Treutler, R. Ahlrichs, Theor. Chem. Acc. 1997, 97, 119-124.
79. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835.
80. a) P. A. M. Dirac, Proc. R. Soc. London Ser. A 1929, 123, 714-733;
81. b) J. C. Slater, Phys. Rev. 1951, 81, 385-390;
82. c) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
83. d) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
84. e) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
85. DGrid, version 4.4, M. Kohout, Radebeul, 2008.