Synthesis, structure, and bonding of weakly coordinating anions based on CN adducts

Journal of the American Chemical Society

Volumn 131, Issue 25, 2009, Pages 8958-8970

  Bernsdorf, Arne ^a   Brand, Harald ^a   Hellmann, Robert ^a   Köckerling, Martin ^a   Schulz, Axel ^a   Villinger, Alexander ^a   Voss, Karsten ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANION FORMATION; CATALYTIC ACTIVITY; COUNTERIONS; DIETHYL ETHERS; EARLY TRANSITION METALS; GOOD YIELD; ION PAIRING; POLAR ORGANIC SOLVENTS; SILVER SALTS; SOLID-STATE STRUCTURES; STRUCTURAL TRENDS; THERMALLY STABLE; WEAK INTERACTIONS; WEAKLY COORDINATING ANIONS;

CATALYSTS; CHARGE TRANSFER; ETHERS; ION EXCHANGE; ORGANIC SOLVENTS; SALTS; STOICHIOMETRY; TRANSITION METAL COMPOUNDS; TRANSITION METALS;

NEGATIVE IONS;

AMIDE; ANION; BORANE DERIVATIVE; BORIC ACID; CARBORANE DERIVATIVE; COORDINATION COMPOUND; DICYANOAMIDE; METAL; METHANTHELINE BROMIDE; ORGANIC SOLVENT; SODIUM CHLORIDE; TETRACYANOBORATE; TRICYANOMETHANIDE; UNCLASSIFIED DRUG; WEAKLY COORDINATING ANION;

ADDUCTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; ELECTRON TRANSPORT; ELECTRONICS; ENERGY TRANSFER; ION PAIR EXTRACTION; MOLECULAR INTERACTION; PHASE TRANSITION; QUANTUM YIELD; SOLID STATE; STEREOSPECIFICITY; STOICHIOMETRY; SYNTHESIS; THERMOSTABILITY;

EID: 67649586416     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902450b     Document Type: Article

References (95)

1. Reviews: (a) Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066.
2. (b) Reed, C. Acc. Chem. Res. 1998, 31, 133.
3. (c) Strauss, S. H. Chem. Rev. 1993, 93, 927, and references therein.
4. (a) Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
5. (b) Bardin, V. V.; Frohn, H. J. Main Group Met. Chem. 2002, 25, 589.
6. (c) Frohn, H. J.; Adonin, N. Y.; Bardin, V. V.; Starichenko, V. F. J. Fluorine Chem. 2002, 117, 115.
7. (c) Bardin, V. V.; Idemskaya, S. G.; Frohn, H. J. Z. Anorg. Allg. Chem. 2002, 628, 883.
8. Plesek, J.; Jelinek, T.; Hermanek, S.; Stibr, B. Collect. Czech. Chem. Commun. 1986, 51, 819.
9. Tsang, C.-W.; Yang, Q.; Tung-Po Sze, E.; Mak, T. C. W; Chan, D. T. W.; Xie, Z. Inorg. Chem. 2000, 39, 5851.
10. Xie, Z.; Tsang, C.-W.; Tung-Po; Sze, E.; Yang, Q.; Chan, D. T. W.; Mak, T. C. W. Inorg. Chem. 1998, 37, 6444.
11. Xie, Z.; Tsang, C.-W.; Xue, F.; Mak, T. C. W. J. Organomet. Chem. 1999, 577, 197.
12. For example: (a) Barbarich, T. J.; Handy, S. T.; Miller, S. M.; Anderson, O. P.; Grieco, P. A.; Strauss, S. H. Organometallics 1996, 15, 3776.
13. (b) Barbarich, T. J.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. J. Mol. Catal. A 1998, 128, 289.
14. (c) Ivanova, S. M.; Nolan, B. G.; Kobayashi, Y.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. Chem. Eur. J 2001, 7, 503.
15. (d) Strauss, S. H.; Nolan, B. G.; Fauber, B. P. WO 00/53611, 2000.
16. (e) Gonsior, M.; Krossing, I.; Mitzel, N. Z. Anorg. Allg. Chem. 2002, 628, 1821.
17. (f) Krossing, I.; Brands, H.; Feuerhake, R.; Koenig, S. J. Fluorine Chem. 2001, 112, 83.
18. (g) Krossing, I. Chem. Eur. J. 2001, 7, 490.
19. (h) Knapp, C.; Mailman, A.; Nikiforov, G. B.; Passmore, J. J. Fluorine Chem. 2006, 127, 1454.
20. (i) Decken, A.; Jenkins, H. D. B.; Nikiforov, G. B.; Passmore, J. Dalton Trans. 2004, (16), 2496.
21. Mercier, H. P. A.; Saunders, J. C. P.; Schrobilgen, G. J. J. Am. Chem. Soc. 1994, 116, 2921.
22. Van Seggen, D. M.; Hurlburt, P. K.; Anderson, O. P.; Strauss, S. H. Inorg. Chem. 1995, 34, 3453.
23. Cameron, T. S.; Krossing, I.; Passmore, J. Inorg. Chem. 2001, 40, 2001.
24. Moran, M. D.; Schrobilgen, G. J.; Steinberg, Ch.; Suontamo, R. J. J. Am. Chem. Soc. 2004, 126, 5533.
25. Raabe, I.; Himmel, D.; Mueller, S.; Trapp, N.; Kaupp, M.; Krossing, I. Dalton Trans. 2008, 946.
26. Krossing, I. J. Am. Chem. Soc. 2001, 123, 4603.
27. Krossing, I.; van Wüllen, L. Chem. Eur. J. 2002, 8, 700.
28. Bihlmeier, A.; Gonsior, M.; Raabe, I.; Trapp, N.; Krossing, I. Chem. Eur. J. 2004, 10, 5041.
29. (a) Bochmann, M.; Jaggar, A. J.; Nicholls, J. C. Angew. Chem., Int. Ed. Engl. 1990, 29, 780.
30. (b) Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1991, 10, 840.
31. (c) Lancaster, S. J.; Walker, D. A.; Thornton-Pett, M.; Bochmann, M. Chem. Commun. 1999, 1533.
32. (d) Zhou, J.; Lancaster, S.J.; Walker, D. A.; Beck, S.; Thornton-Pett, M.; Bochmann, M. J. Am. Chem. Soc. 2001, 123, 223.
33. (e) Hannant, M. H.; Wright, J. A.; Lancaster, S. J.; Hughes, D. L.; Horton, P. N.; Bochmann, M. Dalton Trans. 2006, 16.
34. Lancaster, S. J.; Rodriguez Lara-Sanchez, A.; Hannant, M. D.; Walker, D. A.; Hughes, D. L.; Bochmann, M. Organometallics 2002, 21, 451.
35. LaPointe, R. E. WO99/42467, 1999.
36. LaPointe, R. E.; Roof, G. R.; Abbboud, K. A.; Klosin, J. J. Am. Chem. Soc. 2000, 122, 9560.
37. Wasserscheid, P.; Welton, T. Ionic Liquids in synthesis; Wiley-VCH: 2003.
38. Shobukawa, H.; Tokuda, H.; Susan, A. B. H.; Watanabe, M. Electrochim. Acta 2005, 50, 3872.
39. Shobukawa, H.; Tokuda, H.; Tabata, S.-I.; Watanabe, M. Electrochim. Acta 2004, 50, 1.
40. Seki, S.; Kobayashi, Y.; Miyashiro, H.; Ohno, Y.; Usami, A.; Mita, Y.; Watanabe, M.; Terada, N. Chem. Commun. 2006, 544.
41. Wang, P.; Zakeeruddin, S. M.; Shaik, M.; Humphry-Baker, R.; Grätzel, M. Chem. Mater. 2004, 16, 2694.
42. Wang, P.; Wenger, B.; Humphry-Baker, R.; Moser, J.-E.; Teuscher, J.; Kantlehner, W.; Mezger, J.; Stoyanov, E. V.; Zakeeruddin, S. M.; Grätzel, M. J. Am. Chem. Soc. 2005, 127, 6850.
43. Mazille, F.; Fei, Z.; Kuang, D.; Zhao, D.; Zakeeruddin, S. M.; Grätzel, M.; Dyson, P. J. Inorg. Chem. 2006, 45, 1585.
44. Angell, C. A.; Xu, W. Science 2003, 302, 422.
45. Grimm, H. Z. Elektrochem. 1925, 31, 474.
46. Birckenbach, L.; Kellermann, K. Ber. 1925, 58B, 786.
47. Brand, H.; Schulz, A.; Villinger, A. Z. Anorg. Allg. Chem. 2007, 633, 22.
48. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO Version 3.1.
49. Carpenter, J. E.; Weinhold, F. J. Mol. Struct. (THEOCHEM) 1988, 169, 41.
50. Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum Press: 1988; p 227.
51. Weinhold, F.; Landis, C. Valency and Bonding. A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: 2005. and references therein.
52. Klapötke, T. M.; Schulz, A. Quantum Chemical Methods in Main Group Chemistry; with an invited chapter of R. D. Harcourt about VB Theory; John Wiley & Sons: New York, 1998.
53. Tcb salts; for example: Küppers, T; Bernhardt, E.; Willner, H.; Rohm, H. W.; Köckerling, M. Inorg. Chem. 2005, 44, 1015.
54. Tcm salts; for example: Zhang, L.-Y.; Shi, L.-X; Chern, Z.-N. Inorg. Chem. 2003, 42, 633.
55. Dca salts; for example: Costes, J.-P.; Novotchi, G.; Shova, S.; Dahan, F.; Donnadiue, B.; Tuchagues, J.-P. Inorg. Chem. 2004, 43, 7792.
56. The synthesis of the sodium and trityl salt has been reported. Crystal data are only available of the trityl salt.
57. Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 10581.
58. Siedle, A. R.; Laumanna, W. M. U.S. Patent No. 5,296,433, March 22, 1994.
59. Bradley, D. C.; Keefe, A. D.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Dalton Trans. 1996, 3931.
60. Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
61. Vei, I. C.; Pascu, S. I.; Green, M. L. H.; Green, J. C.; Schilling, R. E.; Anderson, G. D. W.; Rees, L. H. Dalton Trans. 2003, 2550.
62. Danopoulos, A. A.; Galsworthy, J. R.; Green, M. L. H.; Cafferkey, S.; Doerrer, L. H.; Hursthouse, M. B. Chem. Commun. 1998, 2529.
63. Doerrer, L. H.; Galsworthy, J. R.; Green, M. L. H.; Leech, M. A.; Mueller, M. J. Chem. Soc., Dalton Trans. 1998, 3191.
64. Doerrer, L. H.; Galsworthy, J. R.; Green, M. L. H.; Leech, M. A. J. Chem. Soc., Dalton Trans. 1998, 2483.
65. Doerrer, L. H.; Graham, A. J.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 1998, 3941.
66. Doerrer, L. H.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 1999, 4325.
67. Jacobsen, H.; Berke, H.; Doering, S.; Kehr, G.; Erker, G.; Froehlich, R.; Meyer, O. Organometallics 1999, 18, 1724.
68. Irran, E.; Juergens, B.; Schnick, W Chem. Eur. J. 2001, 7, 5372.
69. Witt, J. R. Acta Crystallogr. 1971, B27, 1835.
70. Feller, D.; Dixon, D. J. Phys. Chem. A 2002, 106, 5136.
71. Meerwein, H.; Hederich, V.; Wunderlich, K. Ber. Dtsch. Pharm. Ges. 1958, 291, 541.
72. Hofmann, D. W. M. Acta Crystallogr. 2002, B57, 489.
73. (a) Jenkins, H. D. B.; Glasser, L; Klapötke, T. M.; Crawford, M.-J.; Bhasin, K. K.; Lee, J.; Schrobilgen, G. J.; Sunderlin, L. S.; Liebman, J. F. Inorg. Chem. 2004, 43, 6238.
74. (b) Jenkins, H. D. B.; Liebman, J. F. Inorg. Chem. 2005, 44, 6359.
75. (a) Glasser, L.; Jenkins, H. D. B. Chem. Soc. Rev. 2005, 34, 866.
76. (b) Jenkins, H. D. B.; Roobottom, H. K.; Passmore, J.; Glasser, L. Inorg. Chem. 1999, 38, 3609.
77. (c) Jenkins, H. D. B.; Liebman, J. F. Inorg. Chem. 2005, 44, 6359.
78. +.
79. (a) Goldschmidt, V. M. Chem. Ber. 1927, 60, 1263.
80. (b) Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
81. (c) Glasser, L.; Jenkins, H. D. B. Inorg. Chem. 2008, 47, 6195.
82. Mallouk, T. E.; Rosenthal, G. L.; Muller, G.; Busasco, R.; Barlett, N. Inorg. Chem. 1984, 23, 3167.
83. Preiss, U.; Slattery, J. M.; Krossing, I. Ind. Eng. Chem. Res. 2009, 48, 2290.
84. (a) It is known that for adducts in the solid state and gas phase, structural data and donor - acceptor energies can be quite different. Leopold and co-workers have indicated that the donor - acceptor bond is much shorter in the solid state than in the gas phase, and this change has been associated with the substantial dipole moment of the adduct.
85. (b) Fiacco, D. L; Mo, Y.; Hunt, S. W.; Ott, M. E.; Roberts, A.; Leopold, K. R. J. Phys. Chem. A 2001, 105, 484, and references therein.
86. Kristyán, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175.
87. All calculations were performed using the Gaussian program package: Frisch, M. J.; et al. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
88. For a more thorough discussion on the basis set dependence of molecular geometries, see: Klapötke, T. M.; Schulz, A. Ab initio Methods in Main Group Chemistry; with an invited chapter by R. D. Harcourt about VB Theor;, John Wiley & Sons: New York, 1998.
89. Fischer, C. B.; Xu, S.; Zipse, H. Chem. Eur. J. 2006, 12, 5779.
90. Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc. 1963, 212.
91. Trofimenko, S.; Little, E. L.; Mower, H. F. J. Org. Chem. 1962, 27, 433.
92. Bernhardt, E.; Finze, M.; Willner, H. Z. Anorg. Allg. Chem. 2003, 629, 1229.
93. Sheldrick, G. M. SHELXS-97: Program for the Solution of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
94. Sheldrick, G. M. SHELXL-97: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
95. Sheldrick, G. M. SADABS. Version 2; University of Göttingen: Göttingen, Germany, 2004.