Catalytic abilities of [(C6F5)2BR] (R = NC4H4 and NC4H8) deduced from experimental and theoretical Charge-density investigations

Chemistry - A European Journal

Volumn 15, Issue 18, 2009, Pages 4595-4601

  Flierler, Ulrike ^a   Leusser, Dirk ^a   Ott, Holger ^a   Kehr, Gerald ^b   Erker, Gerhard ^b   Grimme, Stefan ^b   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Boron; Density Functional Calculations; Electron Density; Electronic Structure; Lewis Acids; Nitrogen

Indexed keywords

CATALYTIC ABILITIES; CHARGE-DENSITY; DENSITY FUNCTIONAL CALCULATIONS; DFT CALCULATIONS; ELECTRON DENSITY; ELECTRON-DENSITY DISTRIBUTIONS; HIGH RESOLUTION X-RAY DIFFRACTIONS; LEWIS ACIDS; LOW TEMPERATURES; MULTIPOLE; PENTAFLUOROPHENYL; PYRROLYL; QUANTUM-CHEMICAL CALCULATIONS; TOPOLOGICAL ANALYSIS;

ACIDS; BORON; BORON COMPOUNDS; CARRIER CONCENTRATION; ELECTRON DENSITY MEASUREMENT; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; ELECTRONS; QUANTUM CHEMISTRY; SULFUR COMPOUNDS;

DENSITY FUNCTIONAL THEORY;

EID: 65349167210     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802344     Document Type: Article

References (73)

1. a) X. Yang. C.L. Stern T.J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031;
2. b) P. A. Deck. C. L. Beswick, T.J. Marks, J. Am. Chem. Soc. 1998, 120, 1772-1784;
3. c) Y.-X. Chen, M. V. Metz, L. Li, C. L. Stern, T.J. Marks, J. Am. Chem. Soc. 1998, 120, 6287-6305;
4. d) Review: M. Bochmann, Angew. Chem, 1992, 104, 1206-1207:
5. Angew. Chem. Int. Ed. Engl. 1992, 31, 1181-1182.
6. a) M. Bochmann, S. J. Lancaster, O. B. Robinson, J. Chem. Soc. Chem. Commun. 1995, 2081-2082;
7. b) X. Song, M. Bochmann, J. Organomet. Chem. 1997, 545, 597-600;
8. c) Y. Sun, W. E. Piers, G. P. A. Yap, Organometallics 1997, 16, 2509-2513;
9. d) H. van der Heijden, B. Hessen, A. G. Orpen, J. Am. Chem. Soc. 1998, 120, 1112-1113; reviews:
10. e) W. E. Piers, T. Chivers, Chem. Soc. Rev. 1997, 26, 345-354;
11. f) W. E. Piers, Chem. Eur. J. 1998, 4, 13-18.
12. R. F. Jordan, Adv. Organomet. Chem. 1991, 32, 325-387.
13. a) H. Sinn, W. Kaminsky, Adv. Organomet. Chem. 1980, 18, 99-149;
14. b) M. Bochmann, A.J. Jaggar, J. C. Nicholls, Angew. Chem. 1990, 102, 830-832;
15. Angew. Chem. Int. Ed. Engl. 1990, 29, 780-782;
16. c) J. C. W. Chien, W.-M. Tsai, M. D. Rausch, J. Am. Chem. Soc. 1991, 113, 8570-8571.
17. a) A. G. Massey, A. J. Park, F. G. A. Stone, Proc. Chem. Soc. London 1963, 212;
18. b) A. G. Massey, A. J. Park, J. Organomet. Chem. 1964, 2, 245-250;
19. c) R. F Childs, D.L. Mulholland, Can. J. Chem. 1982, 60, 801-808;
20. d) R. F. Childs, D.L. Mulholland, Can. J. Chem. 1982, 60, 809-812;
21. e) A. G. Massey, A.J. Park in Organometallic Synthesis, Vol 3 (Eds: R. B. King, J. J. Eisch), Elsevier, New York, 1986, p. 461;
22. f) P. Laszlo, M. Teston, J. Am. Chem. Soc. 1990, 112, 8750-8754;
23. g) S. Döring, G. Erker, R. Fröhlich, O. Meyer, K. Bergander, Organometallics 1998, 17, 2183-2187.
24. G. Kehr, R. Fröhlich, B. Wibbeling, G. Erker, Chem. Eur. J. 2000, 6, 258-266.
25. a) P. Coppens, Angew. Chem. 2005, 117, 6970-6972;
26. Angew. Chem. Int. Ed. 2005, 44, 6810-6811;
27. b) H. Ott, D. Stalke, Nachr. Chem. 2008, 56, 131-135.
28. N. K. Hansen, P. Coppens, Acta Crystallogr. Sect. A 1978, 34, 909-921.
29. R. F. W. Bader, Atoms in Molecules - A Quantum Theory, Oxford University Press, New York, 1990.
30. a) T. S. Koritsanszky, P. Coppens, Chem. Rev. 2001, 101, 1583-1627;
31. b) C. Lecomte, M. Souhassou, S. Pillet, J. Mol. Struct. 2003, 647, 53-64;
32. c) C. Gatti, Z. Kristallogr. 2005, 220, 399-457.
33. R. F W. Bader, J. Phys. Chem. A 1998, 102, 7314-7323.
34. R. F W. Bader, H. Essén, J. Chem. Phys. 1984, 80, 1943-1960.
35. 2 bond distance - taken from reference [16a].
36. R. Flaig, T. S. Koritsansky, B. Dittrich, A. Wagner, P. Luger, J. Am. Chem. Soc. 2002, 124, 3407-3417;
37. T. S. Koritsansky, A. Volkov, Chem. Phys. Lett. 2004, 385, 431-434;
38. D.E. Hibbs, J. Overgaard, J. A. Platts, M. P. Waller, M. B. Hursthouse, J. Phys. Chem. B 2004, 108, 3663-3672.
39. a) N. Kocher, J. Henn, B. Gostevskii, D. Kost, I. Kalikhman, B. Engels, D. Stalke, J. Am. Chem. Soc. 2004, 126, 5563-5568;
40. b) N. Kocher, D. Leusser, A. Murso, D. Stalke, Chem. Eur. J. 2004, 10, 3622-3631;
41. c) D. Leusser, J. Henn, N. Kocher, B. Engels, D. Stalke, J. Am. Chem. Soc. 2004, 126, 1781-1793.
42. a) P. Macchi, A. Sironi, Coord. Chem. Rev. 2003, 238, 383-412;
43. b) L. J. Farrugia, C. Evans, M. Tegel, J. Phys. Chem. A 2006, 110, 7952-7961;
44. c) C Gatti, D. Lasi, Faraday Discuss. 2007, 135, 55-78;
45. d) U. Flierler, M. Burzler, D. Leusser, J. Henn, H. Ott, H. Braunschweig, D. Stalke, Angew. Chem. 2008, 120, 4393-4397;
46. Angew. Chem. Int. Ed. 2008, 47, 4321-4325.
47. a) A. Volkov, Y. A. Abramov, P. Coppens, C. Gatti, Acta Crystallogr. Sect. A 2000, 56, 332-339;
48. b) J. Henn, D. Leusser, D. Ilge, D. Stalke, B. Engels, J. Phys. Chem. A 2004, 108, 9442-9452.
49. S. Deuerlein, D. Leusser, U. Flierler, H. Ott, D. Stalke, Organometallics 2008, 27, 2306-2315.
50. C. B. Hübschle, P. Luger, J. Appl. Crystallogr. 2006, 39, 901-904.
51. A. Bach, D. Lentz, P. Luger, J. Phys. Chem. A 2001, 105, 7405-7412.
52. a) W. Scherer, P. Sirsch, D. Shorokhov, M. Tafipolsky, G. S. McGrady, E. Gullo, Chem. Eur. J. 2003, 9, 6057-6070;
53. b) W. Scherer, P. Sirsch, D. Shorokhov, G. S. McGrady, S. A. Mason, M. G. Gardiner, Chem. Eur. J. 2002, 8, 2324-2334.
54. V. Bachler, N. Metzler-Nolte, Eur. J. Inorg. Chem. 1998, 733-744.
55. a) T. Kottke, D. Stalke, J. Appl. Crystallogr. 1993, 26, 615-619;
56. b) D. Stalke, Chem. Soc. Rev. 1998, 27, 171-178.
57. Bruker APEX v2.1-0, Bruker AXS Inst. Inc., Madison, 2007.
58. SAINT v7.23A in Bruker APEX v2.1-0, Bruker AXS Inst. Inc., Madison, 2005.
59. G. M. Sheldrick, SADABS 2006/4, Göttingen, 2006.
60. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
61. F. H. Allen, Acta Crystallogr. Sect. B 1986, 42, 515-522.
62. P. Macchi, P. Coppens, Acta Crystallogr. Sect. A 2001, 57, 656-662.
63. E. Clementi, C. Roetti, At. Data Nucl. Data Tables 1974, 14, 177-478.
64. A. Volkov, Y. A. Abramov, P. Coppens, Acta Crystallogr. Sect. A 2001, 57, 272-282.
65. 2 carbon atoms). Nevertheless, this did not improve the model significantly and the constraints were maintained to lower the number of refined parameters and to avoid correlations.
66. A. Volkov, P. Macchi, L. J. Farrugia, C. Gatti, P. R. Mallinson, T. Richter, T. Koritsanszky, XD2006, A computer program package for multipole refinement, topological analysis of charge densities and evaluation of intermolecular energies from experimental or theoretical structure factors, 2006.
67. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 162, 165-169;
68. TURBOMOLE, version 5.9: R. Ahlrichs, M. Bär, H.-P. Baron, R. Bauernschmitt, S. Böcker, N. Crawford, P. Deglmann, M. Ehrig, E. Eichkorn, S. Elliott, F. Furche, F. Haase, M. Häser, C. Hättig, A. Hellweg, H. Horn, C. Huber, U. Huniar, M. Kattannek, A. Köhn, C. Kölmel, M. Kollwitz, K. May, P. Nava, C. Ochsenfeld, H. Ohm, H. Patzelt, Universität Karlsruhe 2006; see http://www.turbomole.com.
69. A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835;
70. the basis sets are available from the TURBOMOLE homepage via the FTP Server Button (in the subdirectories basen, jbasen, and cbasen); see http://www.turbomole.com.
71. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868;
72. C. Adamo, V. Barone, J. Chem. Phys. 1998, 108, 664-675.
73. F. Biegler-König, J. Schönbohm, D. Bayles, J. Comput. Chem. 2001, 22, 545-559.