Structures, bonding, and reaction chemistry of the neutral organogallium(I) compounds (GaAr)n (n = 1 or 2) (Ar = terphenyl or related ligand): An experimental investigation of Ga-Ga multiple bonding

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2667-2679

  Hardman, Ned J ^a   Wright, Robert J ^a   Phillips, Andrew D ^a   Power, Philip P ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MONOVALENT COMPOUNDS;

BYPRODUCTS; CHEMICAL BONDS; CRYSTAL STRUCTURE; MOLECULAR STRUCTURE; SOLUTIONS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

1,3 BUTADIENE; ALKYNE; BORON; CYCLOHEXANE; DIMER; GALLIUM; LIGAND; ORGANIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM; TERPHENYL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL STRUCTURE; COVALENT BOND; CRYSTAL STRUCTURE; DIMERIZATION; DISSOCIATION; DISSOLUTION; MOLECULAR INTERACTION; MOLECULAR STABILITY; REACTION ANALYSIS; REDUCTION; STEREOSPECIFICITY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0037420323     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028579j     Document Type: Article

References (92)

1. (a) Uhl, W. Coord. Chem. Rev. 1997, 163, 1.
2. (b) Janiak, C. Coord. Chem. Rev. 1997, 163, 107.
3. (c) Uhl, W. Rev. Inorg. Chem. 1998, 18, 239.
4. (d) Linti, G.; Schnöckel, H. Coord. Chem. Rev. 2000, 206-207, 285.
5. (e) Schnöckel, H.; Schnepf, A. Adv. Organomet. Chem. 2001, 47, 235.
6. Loos, D.; Baum, E.; Ecker, H.; Schnöckel, H.; Downs, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 860.
7. Beachley, O. T.; Churchill, M. R.; Fettinger, J. L.; Pazik, J. C.; Victoriano, L. J. Am. Chem. Soc. 1986, 108, 4666.
8. Dohmeier, C.; Robl, C.; Tacke, M.; Schnöckel, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 564.
9. (a) Uhl, W.; Hiller, M.; Layh, M.; Schwarz, W. Angew. Chem., Int. Ed. 1992, 31, 1364.
10. (b) Schluter, R. O.; Cowley, A. H.; Atwood, D. A.; Jones, R. A.; Atwood, J. L. J. Coord. Chem. 1993, 30, 25.
11. (c) Uhl, W.; Graupner, R.; Layh, M.; Schütz, U. J. Organomet. Chem. 1995, 493, C1.
12. (d) Schitter, C.; Roesky, H. W.; Röpken, C.; Herbst-Irmer, R.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1729.
13. (e) Uhl, W.; Keimling, S. U.; Klinkhammer, K. W.; Schwarz, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 64.
14. Schumann, H.; Janiak, C.; Görlitz, F.; Loebel, J.; Dietrich, A. J. Organomet. Chem. 1989, 363, 243.
15. Schumann, H.; Pickhardt, J.; Börner, U. Angew. Chem., Int. Ed. 1987, 26, 790.
16. Beachley, O. T.; Noble, M. J.; Allendoerfer, R. D. J. Organomet. Chem. 1999, 582, 32.
17. Uhl, W.; Cuypers, L.; Harms, K.; Kaim, W.; Wanner, M.; Winter, R.; Koch, R.; Saak, W. Angew. Chem., Int. Ed. 2001, 40, 566.
18. Haubrich, S. T.; Power, P. P. J. Am. Chem. Soc. 1998, 120, 2202.
19. Niemeyer, M.; Power, P. P. Angew. Chem., Int. Ed. 1998, 37, 1277.
20. Su, J.; Li, X.-W.; Crittendon, C.; Robinson, G. H. J. Am. Chem. Soc. 1997, 119, 5471.
21. Klinkhammer, K. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2320; Angew. Chem. 1997, 109, 2414.
22. Klinkhammer, K. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 2320; Angew. Chem. 1997, 109, 2414.
23. Xie, Y.; Grev, R. S.; Su, J.; Schaefer, H. F.; Schleyer, P. v. R.; Su, J.; Li, X.-W.; Robinson, G. H. J. Am. Chem. Soc. 1998, 120, 3773.
24. Bytheway, I.; Lin, Z. J. Am. Chem. Soc. 1998, 120, 12133.
25. Xie, Y.; Schaefer, H. F.; Robinson, G. H. Chem. Phys. Lett. 2000, 317, 174.
26. Grützmacher, H.; Fässler, T. F. Chem.-Eur. J. 2000, 6, 2317.
27. Simons, R. S.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1997, 119, 11705.
28. Cotton, F. A.; Cowley, A. H.; Feng, X. J. Am. Chem. Soc. 1998, 120, 1795.
29. Allen, T. L.; Fink, W. H.; Power, P. P. Dalton Trans. 2000, 407.
30. Bridgeman, A. J.; Ireland, L. R. Polyhedron 2001, 20, 2841.
31. Takagi, N.; Schmidt, M. W.; Nagase, S. Organometallics 2001, 20, 1646.
32. Grunenberg, J.; Goldberg, N. J. Am. Chem. Soc. 2000, 122, 6045.
33. Köppe, R.; Schnöckel, H. Z. Anorg. Allg. Chem. 2000, 626, 1095.
34. Himmel, H.-G.; Schnöckel, H. Chem.-Eur. J. 2002, 8, 10.
35. 2ArGaGaAr model species by two different methods in ref 16. For a very useful discussion of various theoretical approaches as well as ELF calculations, see: Molina, J. M.; Dobado, J. A.; Heard, G. L.; Bader, R. F. W.; Sundberg, M. R. Theor, Chem. Acc. 2001, 105, 365.
36. Twamley, B.; Power, P. P. Angew. Chem., Int. Ed. 2000, 39, 3500.
37. Power, P. P. Dalton Trans. 1998, 2939.
38. Himmel, H.-J.; Manceron, L.; Downs, A. J.; Pullumbi, P. J. Am. Chem. Soc. 2002, 124, 4448.
39. Himmel, H.-J.; Manceron, L.; Downs, A. J.; Pullumbi, P. Angew. Chem., Int. Ed. 2002, 41, 796; Angew. Chem. 2002, 114, 829.
40. Himmel, H.-J.; Manceron, L.; Downs, A. J.; Pullumbi, P. Angew. Chem., Int. Ed. 2002, 41, 796; Angew. Chem. 2002, 114, 829.
41. Downs, A. J.; Himmel, H.-J.; Manceron, L. Polyhedron 2002, 21, 473.
42. Pyykkö, P. Chem. Rev. 1997, 97, 597.
43. Schiemenz, B.; Power, P. P. Organometallics 1996, 15, 958.
44. Schiemenz, B.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 2150.
45. Ruhlandt-Senge, K.; Ellison, J. J.; Wehmschulte, R. J.; Pauer, F.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11353.
46. Hardman, N. J.; Eichler, B. E.; Power, P. P. Chem. Commun. 2000, 1491.
47. Green, M. L. H.; Mountford, P.; Smout, G. J.; Speel, S. R. Polyhedron 1990, 9, 2763.
48. Hope, H. Prog. Inorg. Chem. 1995, 41, 1.
49. (a) SMART: Area-Detector Software Package; Bruker AXS, Inc.: Madison, WI, 1993.
50. (b) SAINT: Area-Detector Integration Software; Bruker AXS. Inc.: Madison, WI, 1995.
51. (c) SADABS: Area-Detector Absorption Correction; Bruker AXS, Inc.: Madison, WI, 1996.
52. (a) SHELXL PC, version 5.03; Bruker AXS, Inc.: Madison, WI, 1994.
53. (b) Cooper, R. I.; Gould, R. O.; Parsons, S.; Watkin, D. J. J. Appl. Crystallogr. 2002, 35, 168.
54. Hardman, N. J.; Wright, R. J.; Phillips, A. D.; Power, P. P. Angew. Chem., Int. Ed. 2002, 41, 2842.
55. Su, J.; Li, X.-W.; Crittendon, R. C.; Campana, C. F.; Robinson, G. H. Organometallics 1997, 16, 4511.
56. Haaland, A.; Martinsen, K.-G.; Volden, H. V.; Loos, D.; Schnöckel, H. Acta Chem. Scand. 1994, 48, 172.
57. Haaland, A.; Martinsen, K.-G.; Volden, H. V.; Kaim, W.; Waldhör, E.; Uhl, W. Organometallics 1996, 15, 1146.
58. Kuchta, M. C.; Bonanno, J. B.; Parkin, G. J. Am. Chem. Soc. 1996, 118, 10914.
59. Wright, R. J.; Phillips, A. D.; Hardman, N. J.; Power, P. P. J. Am. Chem. Soc. 2002, 124, 8538.
60. Uhl, W.; Hiller, W.; Layh, M.; Schwartz, W. Angew. Chem., Int. Ed. Engl. 1991, 30, 173.
61. Uhl, W.; Jantschak, A. J. Organomet. Chem. 1998, 555, 263.
62. Treboux, G.; Barthelat, J.-C. J. Am. Chem. Soc. 1993, 115, 4870.
63. Palagyi, Z.; Schaefer, H. F.; Kapuy, E. Chem. Phys. Lett. 1993, 203, 195.
64. 20 Allen, T. L.; Fink, W. H.; Power, P. P., unpublished work.
65. Alternatively, the GaAr monomer could feature a lone pair orbital that is mostly 4s in character and a Ga - C bond that involves a Ga 4p orbital. When the GaAr species becomes strongly bound through gallium, the character of the gallium bonding orbitals changes to some degree toward sp hybridization so that shorter bonds to gallium are observed.
66. He, X.; Bartlett, R. A.; Olmstead, M. M.; Ruhlandt-Senge, K.; Sturgeon, B. E.; Power, P. P. Angew. Chem., Int. Ed. Engl. 1993, 32, 717.
67. Stender, M.; Eichler, B. E.; Hardman, N. J.; Power, P. P.; Prust, J.; Noltemeyer, M.; Roesky, H. W. Inorg. Chem. 2001, 40, 2794.
68. Cowley, A. H.; Decken, A.; Olazabal, C. A. J. Organomet. Chem. 1996, 524, 27.
69. Hosmane, N. S.; Lu, K.-J.; Zhang, H.; Maguire, J. A. Organometallics 1997, 16, 5163.
70. Schubert, D. M.; Bandman, M. A.; Rees, W. S.; Knobler, C. B.; Lu, P.; Nam, W.; Hawthorne, M. F. Organometallics 1990, 9, 2046.
71. Hardman, N. J.; Power, P. P.; Gorden, J. D.; Macdonald, C. L. B.; Cowley, A. H. Chem. Commun. 2001, 1866.
72. Jutzi, P.; Neumann, B.; Reumann, G.; Schebaum, L. O.; Stammler, H.-G. Organometallics 2001, 20, 2854.
73. For example: Neumuller, B.; Gahlmann, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1710. Kraiter, T.; Neumuller, B. Z. Anorg. Allg. 1995, 621, 597. Kopp, M. R.; Neumuller, B. Z. Anorg. Allg. Chem. 1999, 625, 1413.
74. For example: Neumuller, B.; Gahlmann, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1710. Kraiter, T.; Neumuller, B. Z. Anorg. Allg. 1995, 621, 597. Kopp, M. R.; Neumuller, B. Z. Anorg. Allg. Chem. 1999, 625, 1413.
75. For example: Neumuller, B.; Gahlmann, F. Angew. Chem., Int. Ed. Engl. 1993, 32, 1710. Kraiter, T.; Neumuller, B. Z. Anorg. Allg. 1995, 621, 597. Kopp, M. R.; Neumuller, B. Z. Anorg. Allg. Chem. 1999, 625, 1413.
76. Jacobsen, H.; Berke, H.; Döring, S.; Kehr, G.; Erker, G.; Frölich, R.; Meyer, O. Organometallics 1999, 18, 1724.
77. Gorden, J. D.; Voigt, A.; Macdonald, C. L. B.; Silverman, J. S.; Cowley, A. H. J. Am. Chem. Soc. 2000, 122, 950.
78. Feng, X.; Cotton, F. A. Organometallics 1998, 17, 128.
79. Macdonald, C. L. B.; Cowley, A. H. J. Am. Chem. Soc. 1999, 121, 12113.
80. Uddin, J.; Frenking, G. J. Am. Chem. Soc. 2001, 123, 1683.
81. Reger, D. L.; Garza, D. G. Rheingold, A. L.; Yap, G. P. A. Organometallics 1998, 17, 3624.
82. Jutzi, P.; Neumann, B.; Reumann, G.; Stammler, H.-G. Organometallics 1998, 17, 1305.
83. Martin, L. R.; Einstein, F. W. B.; Pomeroy, R. K. Inorg. Chem. 1985, 24, 2777.
84. He.; X.; Bartlett, R. A.; Power, P. P. Organometallics 1994, 13, 548.
85. Robinson, G. H. Acc. Chem. Res. 1999, 32, 773. Downs, A. J. Coord. Chem. Rev. 1999, 59, 189. Robinson, G. H. Chem. Commun. 2000, 2175. Power, P. P. Struct. Bonding 2002, 103, 57.
86. Robinson, G. H. Acc. Chem. Res. 1999, 32, 773. Downs, A. J. Coord. Chem. Rev. 1999, 59, 189. Robinson, G. H. Chem. Commun. 2000, 2175. Power, P. P. Struct. Bonding 2002, 103, 57.
87. Robinson, G. H. Acc. Chem. Res. 1999, 32, 773. Downs, A. J. Coord. Chem. Rev. 1999, 59, 189. Robinson, G. H. Chem. Commun. 2000, 2175. Power, P. P. Struct. Bonding 2002, 103, 57.
88. Robinson, G. H. Acc. Chem. Res. 1999, 32, 773. Downs, A. J. Coord. Chem. Rev. 1999, 59, 189. Robinson, G. H. Chem. Commun. 2000, 2175. Power, P. P. Struct. Bonding 2002, 103, 57.
89. Eichler, B. E.; Hardman, N. J.; Power, P. P. Angew. Chem., Int. Ed. 2000, 39, 383.
90. Li, X.-W.; Crittendon, R. C.; Robinson, G. H. J. Am. Chem. Soc. 1995, 117, 7578.
91. Li, X.-W.; Xie, Y.; Schreiner, P. R.; Gripper, K. D.; Crittendon, R. C.; Campana, C. F.; Schaefer, H. F.; Robinson, G. H. Organometallics 1996, 15, 3798.
92. Schnöckel, H.; Schnepf, A. Adv. Organomet. Chem. 2001, 47, 235.