From the selective cleavage of the Si-O-Si bond in disiloxanes to zwitterionic, water-stable zinc silanolates

Angewandte Chemie - International Edition

Volumn 48, Issue 43, 2009, Pages 8074-8077

  Däschlein, Christian ^a   O Bauer, Jonathan ^a   Strohmann, Carsten ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH STABILITY; ORGANOSILICON CHEMISTRY; PRESENCE OF WATER; SI-O-SI BOND; SILANOLATES; ZINC SALTS;

CHEMICAL REACTIONS; CHEMICAL RESISTANCE; CHEMICAL STABILITY; SALTS; ZINC; ZINC COMPOUNDS;

SILICON;

EID: 70349970567     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902318     Document Type: Article

References (53)

1. Examples can be found in all commonly used chemistry textbooks. Because of this high stability and low reactivity, silicones have a variety of applications, for example, as insulating compounds, as silicone polymers, as greases, or even as flexible
2. For example, see : R. Murugavel, A. Voigt, M. G. Walawalkar, H. W. Roesky, Chem. Rev. 1996, 96, 2205-2236.
3. For two examples, see: a) F Baud-Grasset, J.-C. Palla, DE69627324T2 11.12. 2003, 2003;
4. b) M. Oka-moto, K. Miyazaki, A. Kado, E. Suzuki, Chem. Commun. 2001, 1838-1839.
5. a) F J. Feher, T. A. Budzichowski, Polyhedron 1995, 14, 3239-3253;
6. b) V. Lorenz, A. Fischer, S. Giess-mann, J. W. Gilje, Y. Gun'ko, K. Jacob, F. T. Edelmann, Coord. Chem. Rev. 2000, 206-207, 321-368;
7. c) J. Beckmann, K. Jurkschat, Coord. Chem. Rev. 2001, 215, 267-300.
8. For selected examples on, for example, stannoxanes, see : a) J. Beckmann, M. Bieseman, K. Hassler, K. Jurkschat, J. C. Martins, M. Schürmann, R. Willem, Inorg. Chem. 1998, 37, 4891-4897;
9. b) M. Schulte, M. Schürmann, D. Dakternieks, K. Jurkschat, Chem. Commun. 1999, 1291-1292;
10. c) J. Beckmann, K. Jurkschat, M. Schürmann, Organometallics 2001, 20, 5125-5133.
11. For some examples and applications, see : a) H. W. Roesky, G. Anantharaman, V. Chandrasekhar, V. Jancik, S. Singh, Chem. Eur. J. 2004, 10, 4106-4114;
12. b) D. E. Leyden, G. H. Luttrell, A. E. Sloan, N. J. De Angelis, Anal. Chim. Acta 1976, 84, 97-108;
13. c) H. C. L. Abbenhuis, Chem. Eur. J. 2000, 6, 25-32;
14. d) R. W. J. M. Hanssen, R. A. Van Santen, H. C. L. Abbenhuis, Eur. J. Inorg. Chem. 2004, 675-683.
15. For examples concerning siloxanes with transition metals, see: F. Schindler, H. Schmidbaur, Angew. Chem. 1967, 79, 697-708;
16. Angew. Chem. Int. Ed. Engl. 1967, 6, 683-694.
17. For examples concerning siloxanes with main-group metals, see : H. Schmidbaur, Angew. Chem. 1965, 77, 206-216;
18. Angew. Chem. Int. Ed. Engl. 1965, 4, 201-211.
19. For examples concerning lithiosilanolates, see: a) H.-W. Lerner, S. Scholz, N. Wiberg, K. Polborn, M. Bolte, M. Wagner, Z. Anorg. Allg. Chem. 2005, 631, 1863-1870;
20. b) B. Kern, H. Vitze, M. Bolte, M. Wagner, H.-W. Lerner, Z. Anorg. Allg. Chem. 2008, 634, 1830-1832.
21. For a good overview of the role of zinc in enzymes, see: G. Parkin, Chem. Rev. 2004, 104, 699-767.
22. D. H. Juers, J. Kim, B. W Matthews, S. M. Sieburth, Biochemistry 2005, 44, 16524-16528.
23. For a related example, see: G Parkin, Chem. Commun. 2000, 1971-1985.
24. For some examples of our aminomethyl-functionalized silanes, see: a) C. Strohmann, C. Däschlein, M. Kellert, D. Auer, Angew. Chem. 2007, 119, 4864-4866;
25. Angew. Chem. Int. Ed. 2007, 46, 4780-4782;
26. b) C. Däschlein, V. H. Gessner, C. Strohmann, Acta Crystallogr. Sect. E 2008, 64, o1950;
27. c) C. Strohmann, C. Däschlein, Organometallics 2008, 27, 2499-2504;
28. d) H. Ott, C. Däschlein, D. Leusser, D. Schildbach, T. Seibel, D. Stalke, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 11901-11911;
29. e) C. Strohmann, J. Hörnig, D. Auer, Chem. Commun. 2002, 766-767;
30. f) C. Strohmann, M. Bindl, V. C. Vraaß, J. Hörnig, Angew. Chem. 2004, 116, 1029-1032;
31. Angew. Chem. Int. Ed. 2004, 43, 1011-1014.
32. For some examples of our amino-functionalized silanes, see: a) C. Strohmann, C. Däschlein, D. Auer, J. Am. Chem. Soc. 2006, 128, 704-705;
33. b) C. Däschlein, C. Strohmann, Eur. J. Inorg. Chem. 2009, 43-52;
34. c) C. Strohmann, C. Däschlein, Chem. Commun. 2008, 2791-2793;
35. d) C. Strohmann, O. Ulbrich, D. Auer, Eur. J. Inorg. Chem. 2001, 1013-1018.
36. For some overview articles concerning the precoordination of metals by amino side arms, see: a) V. H. Gessner, C. Däschlein, C. Strohmann, Chem. Eur. J. 2009, 15, 3320-3334;
37. b) C. M. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276;
38. Angew. Chem. Int. Ed. 2004, 43, 2206-2225;
39. c) P. Beak, A. I. Meyers, Acc. Chem. Res. 1986, 19, 356-363.
40. The use of the organic solvents (acetone and acetonitrile) is only necessary for better crystallization.
41. Gaussian 03 (Revision E.01): Frisch et al., for details see the Supporting Information.
42. For some examples concerning coordination compounds of zinc (fourfold-, fivefold-, and sixfold-coordinated zinc), see : a) F Meyer, Eur. J. Inorg. Chem. 2006, 3789-3800;
43. b) B. Bauer-Siebenlist, S. Dechert, F Meyer, Chem. Eur. J. 2005, 11, 5343-5352;
44. c) B. Bauer-Siebenlist, F Meyer, E. Farkas, D. Vidovic, S. Dechert, Chem. Eur. J. 2005, 11, 4349-4360.
45. N. N. Greenwood, A. Earnshaw, Chemistry of the elements, 1st ed., Pergamon, Oxford (UK), 1984.
46. For one current of the countless examples, see : M. F Bush, J. Oomens, R. J. Saykally, E. R. Williams, J. Am. Chem. Soc. 2008, 130, 6463-6471.
47. For a detailed discussion on the hydrolysis of silanes via pentacoordinated species, see : I. H. Krouse, P. G Wenthold, Organometallics 2004, 23, 2573-2582.
48. For possible future applications of the presented Si-O-Si cleavage and metallasilanolate formation, see: a) M. Sumper, E. Brunner, Adv. Funct. Mater. 2006, 16, 17-26;
49. b) E. Bäuerlein, Angew. Chem. 2003, 115, 636-664;
50. Angew. Chem. Int. Ed. 2003, 42, 614-641;
51. c) M. Sumper, Angew. Chem. 2004, 116, 2301-2304;
52. Angew. Chem. Int. Ed. 2004, 43, 2251-2254;
53. d) M. Sumper, N. Kroger, J. Mater. Chem. 2004, 14, 2059-2065.