Separating electrophilicity and lewis acidity: The synthesis, characterization, and electrochemistry of the electron deficient tris (aryl)boranes B(C6F5)3-n(C6Cl 5)n (n = 1-3)

Journal of the American Chemical Society

Volumn 133, Issue 37, 2011, Pages 14727-14740

  Ashley, Andrew E ^a,c   Herrington, Thomas J ^a   Wildgoose, Gregory G ^b   Zaher, Hasna ^a   Thompson, Amber L ^a   Rees, Nicholas H ^a   Krämer, Tobias ^a   Öhare, Dermot ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT SOLUTION; ELECTROCHEMICAL MEASUREMENTS; ELECTRON WITHDRAWING GROUP; ELECTRON-DEFICIENT; ELECTRONIC EFFECTS; ELECTROPHILICITY; EPR SIGNALS; EXPONENTIAL DECAYS; LEWIS ACIDITY; OPTIMIZED STRUCTURES; PLANAR GEOMETRIES; RADICAL ANIONS; REDUCTION POTENTIAL; REFLUXING; SHIELDING CONSTANTS; SINGLE CRYSTAL X-RAY DIFFRACTION; SPECTROSCOPIC CHARACTERIZATION; SPECTROSCOPIC DATA; STERIC EFFECT; STRUCTURAL DATA; STRUCTURAL REORGANIZATION; STRUCTURE DETERMINATION; VOLTAMMETRIC EXPERIMENTS;

BORON; BORON COMPOUNDS; CHELATION; CRYSTAL STRUCTURE; CYCLIC VOLTAMMETRY; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRONS; GEOMETRY; HYDRIDES; LIGANDS; MOLECULAR SIEVES; PARAMAGNETISM; REDUCTION; SINGLE CRYSTALS; SODIUM; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

CHLORINE COMPOUNDS;

BORANE DERIVATIVE; BORON; HEXANE; LEWIS ACID; TOLUENE; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BINDING; COMPLEX FORMATION; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ELECTROPHILICITY; FLUORINE NUCLEAR MAGNETIC RESONANCE; MOLECULAR STABILITY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SURFACE CHARGE; SYNTHESIS; VACUUM; X RAY DIFFRACTION;

EID: 80052801419     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205037t     Document Type: Article

References (105)

1. Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc., London 1963, 212
2. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245-250
3. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1966, 5, 218-225
4. Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J. X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179-6186
5. Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921-3923
6. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440-9441
7. Morrison, D. J.; Piers, W. E. Org. Lett. 2003, 5, 2857-2860
8. Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887-4892
9. Morrison, D. J.; Blackwell, J. M.; Piers, W. E. Pure Appl. Chem. 2004, 76, 615-623
10. Krossing, I.; Raabe, I. Angew. Chem., Int. Ed. 2004, 43, 2066-2090
11. Bochmann, M.; Lancaster, S. J.; Hannant, M. D.; Rodriguez, A.; Schormann, M.; Walker, D. A.; Woodman, T. J. Pure Appl. Chem. 2003, 75, 1183-1195
12. Lancaster, S. J.; Walker, D. A.; Thornton-Pett, M.; Bochmann, M. Chem. Commun. 1999, 1533-1534
13. Lancaster, S. J.; Rodriguez, A.; Lara-Sanchez, A.; Hannant, M. D.; Walker, D. A.; Hughes, D. H.; Bochmann, M. Organometallics 2002, 21, 451-453
14. LaPointe, R. E.; Roof, G. R.; Abboud, K. A.; Klosin, J. J. Am. Chem. Soc. 2000, 122, 9560-9561
15. Yang, X. M.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015-10031
16. Bernsdorf, A.; Brand, H.; Hellmann, R.; Kockerling, M.; Schulz, A.; Villinger, A.; Voss, K. J. Am. Chem. Soc. 2009, 131, 8958-8970
17. Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434
18. Beckett, M. A.; Brassington, D. S.; Coles, S. J.; Hursthouse, M. B. Inorg. Chem. Commun. 2000, 3, 530-533
19. Jacobsen, H.; Berke, H.; Doring, S.; Kehr, G.; Erker, G.; Frohlich, R.; Meyer, O. Organometallics 1999, 18, 1724-1735
20. Erker, G. Dalton Trans. 2005, 1883-1890
21. Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354
22. Stephan, D. W. Dalton Trans. 2009, 3129-3136
23. Kenward, A. L.; Piers, W. E. Angew. Chem., Int. Ed. 2008, 47, 38-41
24. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46-76
25. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396-8397
26. Chen, C.; Eweiner, F.; Wibbeling, B.; Froehlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem.-Asian J. 2010, 5, 2199-2208
27. Chen, C.; Froehlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2010, 46, 3580-3582
28. Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6422-6432
29. Dureen, M. A.; Brown, C. C.; Stephan, D. W. Organometallics 2010, 29, 6594-6607
30. Jiang, C.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125-133
31. Moemming, C. M.; Froemel, S.; Kehr, G.; Froehlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131, 12280-12289
32. Sortais, J.-B.; Voss, T.; Kehr, G.; Froehlich, R.; Erker, G. Chem. Commun. 2009, 7417-7418
33. Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem. Eur. J. 2010, 16, 3005-3008
34. Momming, C. M.; Otten, E.; Kehr, G.; Frohlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2009, 48, 6643-6646
35. Zhao, X.; Stephan, D. W. Chem. Commun. 2011, 47, 1833-1835
36. Appelt, C.; Westenberg, H.; Bertini, F.; Ehlers, A. W.; Slootweg, J. C.; Lammertsma, K.; Uhl, W. Angew. Chem., Int. Ed. 2011, 50, 3925-3928
37. Tran, S. D.; Tronic, T. A.; Kaminsky, W.; Heinekey, D. M.; Mayer, J. M. Inorg. Chim. Acta 2011, 369, 126-132
38. Neu, R. C.; Otten, E.; Lough, A.; Stephan, D. W. Chem. Sci. 2011, 2, 170-176
39. Otten, E.; Neu, R. C.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 9918-9919
40. Ashley, A. E.; Thompson, A. L.; ÖHare, D. Angew. Chem., Int. Ed. 2009, 48, 9839-9843
41. Menard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796-1797
42. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Froehlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543-7546
43. Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701-1703
44. Beckett, M. A.; Strickland, G. C.; Holland, J. R.; Varma, K. S. Polymer 1996, 37, 4629-4631
45. Eros, G.; Mehdi, H.; Papai, I.; Rokob, T. A.; Kiraly, P.; Tarkanyi, G.; Soos, T. Angew. Chem., Int. Ed. 2010, 49, 6559-6563
46. Piers, W. E.; Irvine, G. J.; Williams, V. C. Eur. J. Inorg. Chem. 2000, 2131-2142
47. McDaniel, D. S.; Brown, H. C. J. Org. Chem. 1958, 23, 420-427
48. Christoph Elschenbroich, A. S. Organometallics: A Concise Introduction, 2 nd ed.; Wiley VCH: Weinheim, 1992.
49. Niedenzu, K. Organomet. Chem. Rev. 1966, 1, 305-329
50. Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492-5503
51. Sundararaman, A.; Jakle, F. J. Organomet. Chem. 2003, 681, 134-142
52. Rausch, M. D., Tibbetts, F. E., and Gordon, H. B. J. Organomet. Chem. 1966, 5, 493
53. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126
54. Chivers, T.; David, B. J. Organomet. Chem. 1968, 13, 177-186
55. Williams, V. C.; Piers, W. E.; Clegg, W.; Elsegood, M. R. J.; Collins, S.; Marder, T. B. J. Am. Chem. Soc. 1999, 121, 3244-3245
56. Horton, A. D.; deWith, J. Organometallics 1997, 16, 5424-5436
57. Blake, A. J.; Cole, J. M.; Evans, J. S. O.; Main, P.; Parsons, S.; Watkin, D. J. Crystal Structure Analysis: Principles and Practice, 2 nd ed.; Oxford University Press: Oxford, 2009.
58. Tulinsky, A.; White, J. G. Acta Crystallogr. 1958, 11, 7-14
59. Power, P. P.; Olmstead, M. M. J. Am. Chem. Soc. 1986, 108, 4253-4236
60. Zettler, F.; Hausen, H. D.; Hess, H. J. Organomet. Chem. 1974, 72, 157-162
61. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1966, 5, 218-225
62. Danopoulos, A. A.; Galsworthy, J. R.; Green, M. L. H.; Cafferkey, S.; Doerrer, L. H.; Hursthouse, M. B. Chem. Commun. 1998, 2529-2530
63. Doerrer, L. H.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 1999, 4325-4329
64. Beringhelli, T.; Maggioni, D.; D'Alfonso, G. Organometallics 2001, 20, 4927-4938
65. Timoshkin, A. Y.; Frenking, G. Organometallics 2008, 27, 371-380
66. Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 10581-10590
67. Bergquist, C.; Parkin, G. J. Am. Chem. Soc. 1999, 121, 6322-6323
68. Childs, R. F.; Mulholland, D. L.; Nixon, A. Can. J. Chem. 1982, 60, 801-808
69. Lappert, M. F. J. Chem Soc. 1961, 817
70. Lappert, M. F. J. Chem Soc. 1962, 542
71. Mayer, U.; Gutmann, V.; Gerger, W. Monatsh. Chem. 1975, 106, 1235-1257
72. Gutmann, V. Coord. Chem. Rev. 1976, 18, 225-255
73. Welch, G. C.; Cabrera, L.; Chase, P. A.; Hollink, E.; Masuda, J. D.; Wei, P. R.; Stephan, D. W. Dalton Trans. 2007, 3407-3414
74. Beckett, M. A.; Strickland, G. C.; Holland, J. R.; Varma, K. S. Polymer 1996, 37, 4629-4631
75. Britovsek, G. J. P.; Ugolotti, J.; White, A. J. P. Organometallics 2005, 24, 1685-1691
76. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533
77. Mackle, H.; Sutton, L. E. Trans. Faraday Soc. 1951, 47, 691-699
78. Bandoli, G.; Bortoloz., G; Clemente, D. A.; Croatto, U.; Panatton., C J. Chem. Soc. A 1970, 2778
79. Harlan, C. J.; Hascall, T.; Fujita, E.; Norton, J. R. J. Am. Chem. Soc. 1999, 121, 7274-7275
80. Cummings, S. A.; Iimura, M.; Harlan, C. J.; Kwaan, R. J.; Trieu, I. V.; Norton, J. R.; Bridgewater, B. M.; Jakle, F.; Sundararaman, A.; Tilset, M. Organometallics 2006, 25, 1565-1568
81. Compton, R. G.; Banks, C. E. Understanding Voltammetry; World Scientific Publishing: Singapore, 2007.
82. Testa, A. C.; Reinmuth, W. H. Anal. Chem. 1961, 33, 1320-1324
83. Ballester, M.; Riera-Figueras, J.; Castaner, J.; Badfa, C.; Monso, J. M. J. Am. Chem. Soc. 1971, 93, 2215-2225
84. Ballester, M. Acc. Chem. Res. 1985, 18, 380-387
85. Chivers, T.; Schatte, G. Eur. J. Inorg. Chem. 2003, 3314-3317
86. Strauss, S. H. Chem. Rev. 1993, 93, 927-942
87. Frohn, H. J.; Jakobs, S. J. Chem. Soc., Chem. Commun. 1989, 625-627
88. Gritzner, G.; Kuta, J. Pure Appl. Chem. 1984, 56, 461
89. Kwaan, R. J.; Harlan, C. J.; Norton, J. R. Organometallics 2001, 20, 3818-3820
90. Cairncross, A.; Sheppard, W. A.; Wonchoba, E. Org. Synth. 1988, 50-9, 875-882
91. Cosier, J.; Glazer, A. M. J. Appl. Crystallogr. 1986, 19, 105-107
92. Otwinowski, Z.; Minor, W Processing of X-ray Diffraction Data Collected in Oscillation Mode In Methods in Enzymology; Carter, C. W.; Sweet, R. M., Eds.; Academic Press: New York, 1997; p 276.
93. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435
94. Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.; Prout, K.; Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487
95. Cooper, R. I.; Thompson, A. L.; Watkin, D. J. J. Appl. Crystallogr. 2010, 43, 1100-1107
96. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
97. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
98. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
99. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
100. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835
101. Frisch, M. J. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford CT, 2003.
102. Ditchfield, R. Mol. Phys. 1974, 27, 789-807
103. Wolinski, K.; Hinton, J. F.; Pulay, P. J. J. Am. Chem. Soc. 1990, 112, 8251-8260
104. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
105. Jensen, F. J. Chem. Theory Comput. 2008, 4, 719-727