Bismuth-arene π-interaction: A combined experimental and theoretical approach

Organometallics

Volumn 28, Issue 18, 2009, Pages 5405-5411

  Auer, Alexander A ^a   Nolde, Christoph ^a   Mansfeld, Dirk ^b   Schneider, Wolfgang ^a   Schürmann, Markus ^b   Mehring, Michael ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BONDING SITUATION; EXPERIMENTAL VALUES; INTERACTION ENERGIES; MODEL COMPOUND; QUANTUM-MECHANICAL STUDY; SINGLE-CRYSTAL STRUCTURE ANALYSIS; STACKING INTERACTION; THEORETICAL APPROACH; THEORETICAL STUDY; TWO-DIMENSIONAL NETWORKS;

BISMUTH;

BISMUTH COMPOUNDS;

EID: 70349319974     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900536r     Document Type: Article

References (81)

1. Letin, J. M. Supramolecular Chemistry; VCH: Wemheim, Germany, 1995.
2. Lehn, J. M. Angew. Chem., Int. Ed. 1990, 29, 1304.
3. Badjic, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull,W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723.
4. Descalzo, A. B.; Martinez-Manez, R.; Sancenon, R.; Hoffmann, K.; Rurack, K. Angew. Chem., Int. Ed. 2006, 45, 5924.
5. Gamez, P.; Mooibroek, T. J.; Teat, S. J.; Reedijk, J. Acc. Chem. Res. 2007, 40, 435.
6. Katz, M. J.; Sakai, K.; Leznoff, D. B. Chem. Soc. Rev. 2008, 37, 1884.
7. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114.
8. Schalley, C. A. Mass Spectrom. Rev. 2001, 20, 253.
9. Schneider, H. J.; Yatsimirsky, A. K. Chem. Soc. Rev. 2008, 37, 263.
10. Schneider, H. J. Angew. Chem., Int. Ed. 2009, 48, 3924.
11. Schmidbaur, H.; Schier, A. Chem. Soc. Rev. 2008, 37, 1931.
12. Schmidbaur, H.; Schier, A. Organometallics 2008, 27, 2361.
13. Silvestru, C.; Breunig, H. J.; Althaus, H. Chem. Rev. 1999, 99, 3277.
14. Menshutkin, B. N. J. Russ. Phys. Chem. Soc 1911, 43, 1294.
15. Menshutkin, B. N. J. Russ. Phys. Chem. Soc 1911, 43, 1805.
16. Menshutkin, B. N. J. Russ. Phys. Chem. Soc 1912, 44, 1079.
17. Hulme, R.; Szymanski, J. T. Acta Crystallogr. B 1969, 25, 753.
18. Schier, A.; Wallis, J. M.; Müller, G.; Schmidbaur, H. Angew. Chem., Int. Ed. Engl. 1986, 25, 757.
19. Frank, W.; Weber, J.; Fuchs, E. Angew. Chem., Int. Ed. Engl. 1987, 26, 74.
20. Clegg, W.; Errington, R. J.; Fisher, G. A.; Hockless, D. C. R.; Norman, N. C.; Orpen, A. G.; Stratford, S. E. J. Chem. Soc., Dalton Trans. 1992, 1967.
21. (a) Jones, C. M.; Burkart, M. D.; Serra, D. L.; Hwu, S. J.; Whitmire, K. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 451.
22. (b) Jones, C. M.; Burkart, M. D.; Bachman, R. E.; Serra, D. L.; Hwu, S. J.; Whitmire, K. H. Inorg. Chem. 1993, 52, 5136.
23. Stavila, V.; Dikarev, E. V. J. Organomet. Chem. 2009, 694, 2956.
24. Frank, W.; Reiland, V.; Reiss, G. J. Angew. Chem., Int. Ed. 1998, 37, 2984.
25. Becker, G.; Egner, J.; Meiser, M.; Mundt, O.; Weidlein, J. Z. Anorg. AlIg. Chem. 1997, 623, 941.
26. Mansfeld, D.; Mehring, M.; Schürmann, M. Z. Anorg. Allg. Chem. 2004, 630, 1795.
27. Mehring, M.; Schürmann, M. Chem. Commun. 2001, 2354.
28. Breunig, H. J.; Haddad, N.; Lork, E.; Mehring, M.; Mügge, C.; Nolde, C.; Rat, C. I.; Schürmann, M. Organometallics 2009, 28, 1202.
29. Frank, W.; Schneider, J.; Müller-Becker, S. J. Chem. Soc., Chem. Commun. 1993, 799.
30. Müller-Becker, S.; Frank, W.; Schneider, J. Z. Anorg. AlIg. Chem. 1993, 619, 1073.
31. Ferrari, M. B.; Cramarossa, M. R.; Iarossi, D.; Pelosi, G. Inorg. Chem. 1998, 57, 5681.
32. Battaglia, L. P.; Bellitto, C.; Cramarossa, M. R.; Vezzosi, I. M. Inorg. Chem. 1996, 35, 2390.
33. Battaglia, L. P.; Cramarossa, M. R.; Vezzosi, I. M. Inorg. Chim. Acta 1995, 237, 169.
34. Vezzosi, I. M.; Battaglia, L. P.; Corradi, A. B. J. Chem. Soc., Dalton Trans. 1992, 375.
35. Probst, T.; Steigelmann, O.; Riede, J.; Schmidbaur, H. Chem. Ber. 1991, 124, 1089.
36. Battaglia, L. P.; Corradi, A. B.; Vezzosi, I. M.; Zanoli, F. A. J. Chem. Soc., Dalton Trans. 1990, 1675.
37. Vezzosi, I. M.; Zanoli, A. F.; Battaglia, L. P.; Corradi, A. B. J. Chem. Soc., Dalton Trans. 1988, 191.
38. Schmidbaur, H.; Nowak, R.; Schier, A.; Wallis, J. M.; Huber, B.; Müller, G. Chem. Ber. Rec. 1987, 120, 1829.
39. Schmidbaur, H.;Wallis, J. M.; Nowak, R.; Huber, B.; Müller, G. Chem. Ber. Rec. 1987, 120, 1837.
40. Konietzny, S. Dissertation, University of Kaiserslautern, 2003.
41. Dikarev, E. V.; Li, B.; Rogachev, A. Y.; Zhang, H. T.; Petrukhina, M. A. Organometallics 2008, 27, 3728.
42. Turner, L. E.; Davidson, M. G.; Jones, M. D.; Ott, H.; Schulz, V. S.; Wilson, P. J. Inorg. Chem. 2006, 45, 6123.
43. Bahr, G.; Zoche, G. Chem. Ber 1957, 90, 1176.
44. Bondi, A. J. Phys. Chem. 1964, 68, 441.
45. Suzuki, H.; Matano, Y. Organobismuth Chemistry; Elsevier: Amsterdam, 2001.
46. Batsanov, S. S. Izv. Akad. Nauk., Ser. Khim 1995, 18.
47. Mansfeld, D.; Mehring, M.; Schürmann, M. Angew. Chem., Int. Ed. 2005, 44, 245.
48. Mehring, M.; Paalasmaa, S.; Schürmann, M. Eur. J. Inorg. Chem. 2005, 4891.
49. Mehring, M.; Mansfeld, D.; Paalasmaa, S.; Schürmann, M. Chem.-Eur. J. 2006, 12, 1161.
50. Mehring, M.; Mansfeld, D.; Costisella, B.; Schürmann, M. Eur. J. Inorg. Chem. 2006, 735.
51. Wetzel, J. Z. Kristallogr., Kristallgeom., Kristallphys., Kristalchem. 1942, 104, 305.
52. Hawley, D. M.; Ferguson, G. J. Chem. Soc. 1968, 2059.
53. Jones, P. G.; Blaschette, A.; Henschel, D.; Weitze, A. Z. Kristallogr. 1995, 210, 377.
54. 1 with a=24.215(5) ̊, b=16.283(3) ̊, c=7.643(2) ̊ and Z=4. Polymorph B crystallizes in the monoclinic space group P21/c with a= 15.349(3) ̊, b = 11.257(2) ̊, c=18.468(4) ̊, β=110.64(3) ° and Z=4. Reference 50 refers to a third polymorph, C, which crystallizes in the triclinic space group P-1 with a= 19.430 ̊, b=17.720 ̊, c=11.140 ̊, α=80.15°, β=128.47°, γ =99.97° and Z=8. References 51 and 52 refer to a fourth polymorph, D, which crystallizes in the monoclinic space group C2/c with a=27.515(6) ̊, b=5.728(2) ̊, c=20.273(5) ̊, β=114.30(3)° and Z=8.
55. Clegg, W.; Elsegood, M. R. J.; Errington, R. J.; Fisher, G. A.; Norman, N. C. J. Mater. Chem. 1994, 4, 891.
56. Anderson, K. M.; Baylies, C. J.; Jahan, A.; Norman, N. C.; Orpen, A. G.; Starbuck, J. Dalton Trans. 2003, 3270.
57. Lee, E. C.; Kim, D.; Jurecka, P.; Tarakeshwar, P.; Hobza, P.; Kim, K. S. J. Phys. Chem. A 2007, 111, 3446.
58. Kristyan, S.; Pulay, P. Chem. Phys. Lett. 1994, 229, 175.
59. Hobza, P.; Sponer, J.; Reschel, T. J. Comput. Chem. 1995, 16, 1315.
60. Dobson, J. F.; McLennan, K.; Rubio, A.; Wang, J.; Gould, T.; Le, H. M.; Dinte, B. P. Aust. J. Chem. 2001, 54, 513.
61. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
62. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
63. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
64. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
65. 3 (X=Cl, Br) are in good agreement with experimental data from electron diffraction: (a) Toke, O.; Hargittai, M. Struct. Chem. 1995, 6, 127.
66. (b) Haaland, A.; Hougen, J.; Samdal, S.; Tremmel, J. Acta Chem. Scand. 1998, A42, 409.
67. Grimme, S. Angew. Chem., Int. Ed. 2008, 47, 3430.
68. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 461.
69. Sheldrick, G. M. SHELXL-97; University of Göttingen 1997.
70. International Tables for Crystallography; Kluwer Academic Publishers: Dordrecht, Vol.C.
71. Sheldrick, G. M.SHELXTL, Release 5.1 Reference Manual, Bruker AXS, Inc.: Madison, WI, 1997.
72. Brandenburg, K. Diamond, Version 3.1f; Crystal Impact GbR: Bonn, Germany, 2008.
73. Ahlrichs, R.; Bar, M.; Haser, M.; Horn, H.; Kolmel, C. Chem. Phys. Lett. 1989, 162, 165.
74. Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346.
75. Bylaska, E. J.; de Jong, W. A.; Govind, N.; Kowalski, K.; Straatsma, T. P.; Valiev, M.; Wang, D.; Apra, E.; Windus, T. L.; Hammond, J.; Nichols, P.; Hirata, S.; Hackler, M. T.; Zhao, Y.; Fan, P.-D.; Harrison, R. J.; Dupuis, M.; Smith, D. M. A.; Nieplocha, J.; Tipparaju, V.; Krishnan, M.; Wu, Q.; T. Van Voorhis, Auer, A. A.; Nooijen, M.; Brown, E.; Cisneros, G.; Fann, G. I.; Fruchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J. A.; Tsemekhman, K.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Pollack, L.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; J. van Lenthe, Wong, A.; Zhang, Z. NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1; Pacific Northwest National Laboratory: Richland, WA, 2007.
76. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7, 3297.
77. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
78. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
79. Weigend, F.; Häser, M. Theor. Chem. Acc. 1997, 97, 331.
80. Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143.
81. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.