Dipalladium(I) terphenyl diphosphine complexes as models for two-site adsorption and activation of organic molecules

Journal of the American Chemical Society

Volumn 135, Issue 42, 2013, Pages 15830-15840

  Lin, Sibo ^a   Herbert, David E ^a   Velian, Alexandra ^a   Day, Michael W ^a   Agapie, Theodor ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; BINDING SITES; DENSITY FUNCTIONAL THEORY; EQUILIBRIUM CONSTANTS; MOLECULAR ORBITALS; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIOPHENE; TOLUENE;

1 ,3-CYCLOHEXADIENE; COMPREHENSIVE ANALYSIS; ELECTROSTATIC POTENTIALS; LIGAND SUBSTITUTION; NUCLEAR MAGNETIC RESONANCE(NMR); ORDERS OF MAGNITUDE; RELATIVE BINDING STRENGTHS; STRUCTURAL CHARACTERIZATION;

LIGANDS;

1,3 BUTADIENE; 1,3 CYCLOHEXADIENE; ANISOLE; BENZOTHIOPHENE; DIPALLADIUM TERPHENYL DIPHOSPHINE TOLUENE CAPPED COMPLEX; FURAN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; PYRROLE; THIOPHENE; TOLUENE; UNCLASSIFIED DRUG; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE; TERPHENYL DERIVATIVE;

ADSORPTION; ARTICLE; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; DENSITY FUNCTIONAL THEORY; EQUILIBRIUM CONSTANT; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROOM TEMPERATURE; SYNTHESIS; CHEMISTRY; QUANTUM THEORY; SURFACE PROPERTY; X RAY CRYSTALLOGRAPHY;

ADSORPTION; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; QUANTUM THEORY; SURFACE PROPERTIES; TERPHENYL COMPOUNDS;

EID: 84886523244     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja406696k     Document Type: Article

References (85)

1. Hafner, J. Monatsh. Chem. 2008, 139, 373
2. Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249
3. Augustine, R. L.; O'Leary, S. T. J. Mol. Catal. A: Chem. 1995, 95, 277
4. Prins, R.; Egorova, M.; Röthlisberger, A.; Zhao, Y.; Sivasankar, N.; Kukula, P. Catal. Today 2006, 111, 84
5. Girgis, M. J.; Gates, B. C. Ind. Eng. Chem. Res. 1991, 30, 2021
6. Murahashi, T.; Kimura, S.; Takase, K.; Ogoshi, S.; Yamamoto, K. Chem. Commun. 2013, 49, 4310
7. Murahashi, T.; Nagai, T.; Okuno, T.; Matsutani, T.; Kurosawa, H. Chem. Commun. 2000, 1689
8. Murahashi, T.; Kurosawa, H. Coord. Chem. Rev. 2002, 231, 207
9. Paton, R. S.; Brown, J. M. Angew. Chem., Int. Ed. 2012, 51, 10448
10. Allegra, G.; Tettamanti Casagrande, G.; Immirzi, A.; Porri, L.; Vitulli, G. J. Am. Chem. Soc. 1970, 92, 289
11. Dupont, J.; Pfeffer, M.; Rotteveel, M. A.; De Cian, A.; Fischer, J. Organometallics 1989, 8, 1116
12. Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97
13. Åkerstedt, J.; Gorlov, M.; Fischer, A.; Kloo, L. J. Organomet. Chem. 2010, 695, 1513
14. Dotta, P.; Kumar, P. G. A.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2004, 23, 4247
15. Barder, T. E. J. Am. Chem. Soc. 2005, 128, 898
16. Christmann, U.; Pantazis, D. A.; Benet-Buchholz, J.; McGrady, J. E.; Maseras, F.; Vilar, R. n. J. Am. Chem. Soc. 2006, 128, 6376
17. Murahashi, T.; Takase, K.; Oka, M.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 14908
18. Murahashi, T.; Fujimoto, M.; Oka, M.; Hashimoto, Y.; Uemura, T.; Tatsumi, Y.; Nakao, Y.; Ikeda, A.; Sakaki, S.; Kurosawa, H. Science 2006, 313, 1104
19. Murahashi, T.; Otani, T.; Mochizuki, E.; Kai, Y.; Kurosawa, H.; Sakaki, S. J. Am. Chem. Soc. 1998, 120, 4536
20. Murahashi, T.; Kanehisa, N.; Kai, Y.; Otani, T.; Kurosawa, H. Chem. Commun. 1996, 825
21. Leoni, P.; Pasquali, M.; Sommovigo, M.; Albinati, A.; Lianza, F.; Pregosin, P. S.; Ruegger, H. Organometallics 1993, 12, 4503
22. Werner, H.; Kühn, A.; Tune, D. J.; Krüger, C.; Brauer, D. J.; Sekutowski, J. C.; Tsay, Y.-h. Chem. Ber. 1977, 110, 1763
23. Werner, H.; Kraus, H.-J.; Schubert, U.; Ackermann, K. Chem. Ber. 1982, 115, 2905
24. Hruszkewycz, D. P.; Wu, J.; Hazari, N.; Incarvito, C. D. J. Am. Chem. Soc. 2011, 133, 3280
25. Kobayashi, Y.; Iitaka, Y.; Yamazaki, H. Acta Crystallogr., B 1972, 28, 899
26. Sui-Seng, C.; Enright, G. D.; Zargarian, D. J. Am. Chem. Soc. 2006, 128, 6508
27. Markert, C.; Neuburger, M.; Kulicke, K.; Meuwly, M.; Pfaltz, A. Angew. Chem., Int. Ed. 2007, 46, 5892
28. Velian, A.; Lin, S.; Miller, A. J. M.; Day, M. W.; Agapie, T. J. Am. Chem. Soc. 2010, 132, 6296
29. Lin, S.; Day, M. W.; Agapie, T. J. Am. Chem. Soc. 2011, 133, 3828
30. Chao, S. T.; Lara, N. C.; Lin, S.; Day, M. W.; Agapie, T. Angew. Chem., Int. Ed. 2011, 50, 7529
31. Kelley, P.; Lin, S.; Edouard, G.; Day, M. W.; Agapie, T. J. Am. Chem. Soc. 2012, 134, 5480
32. Kaye, G. W. C.; Laby, T. H. Tables of Physical and Chemical Constants; 15 th ed.; Longmon: London, U.K., 1993.
33. Efremenko, I. J. Mol. Catal. A: Chem. 2001, 173, 19
34. Brandenburg, K. DIAMOND. Crystal Impact GbR, Bonn, Germany, 1999.
35. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176
36. Katano, S.; Ichihara, S.; Ogasawara, H.; Kato, H. S.; Komeda, T.; Kawai, M.; Domen, K. Surf. Sci. 2002, 502-503, 164
37. Murahashi, T.; Kurosawa, H. J. Organomet. Chem. 1999, 574, 142
38. Reiß, G. J.; Konietzny, S. J. Chem. Soc., Dalton Trans. 2002, 862
39. Tatsumi, Y.; Naga, T.; Nakashima, H.; Murahashi, T.; Kurosawa, H. Chem. Commun. 2004, 1430
40. Saeys, M.; Reyniers, M. F.; Neurock, M.; Marin, G. B. Surf. Sci. 2006, 600, 3121
41. Harshbarger, W. R.; Bauer, S. H. Acta Crystallogr., B 1970, 26, 1010
42. Harman, W. D. Coord. Chem. Rev. 2004, 248, 853
43. Keane, J. M.; Harman, W. D. Organometallics 2005, 24, 1786
44. Delafuente, D. A.; Myers, W. H.; Sabat, M.; Harman, W. D. Organometallics 2005, 24, 1876
45. Ateşin, T. A.; Jones, W. D. Organometallics 2007, 27, 53
46. Ateşin, T. A.; Jones, W. D. Organometallics 2008, 27, 3666
47. Hachgenei, J. W.; Angelici, R. J. Organometallics 1989, 8, 14
48. Angelici, R. J. Organometallics 2001, 20, 1259
49. Janak, K. E.; Tanski, J. M.; Churchill, D. G.; Parkin, G. J. Am. Chem. Soc. 2002, 124, 4182
50. Sattler, A.; Janak, K. E.; Parkin, G. Inorg. Chim. Acta 2011, 369, 197
51. Vicic, D. A.; Jones, W. D. J. Am. Chem. Soc. 1999, 121, 7606
52. Jones, W. D.; Chin, R. M.; Hoaglin, C. L. Organometallics 1999, 18, 1786
53. Jones, W. D.; Chin, R. M. Organometallics 1992, 11, 2698
54. Capon, J.-F.; Schollhammer, P.; Pétillon, F. o. Y.; Talarmin, J.; Muir, K. W. Organometallics 1999, 18, 2055
55. Grochowski, M. R.; Li, T.; Brennessel, W. W.; Jones, W. D. J. Am. Chem. Soc. 2010, 132, 12412
56. Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649
57. Terada, S.; Yokoyama, T.; Sakano, M.; Imanishi, A.; Kitajima, Y.; Kiguchi, M.; Okamoto, Y.; Ohta, T. Surf. Sci. 1998, 414, 107
58. Schwalbe, M.; Walther, D.; Schreer, H.; Langer, J.; Görls, H. J. Organomet. Chem. 2006, 691, 4868
59. Orita, H.; Itoh, N. Surf. Sci. 2004, 550, 177
60. Such a motif (with S bound to a third metal) has been proposed in a DFT study of thiophene on Pt(111) Zhu, H.; Guo, W.; Li, M.; Zhao, L.; Li, S.; Li, Y.; Lu, X.; Shan, H. ACS Catal. 2011, 1, 1498
61. Adams, R. D.; Qu, X. Organometallics 1995, 14, 2238
62. Kabir, S. E.; Miah, M. A.; Sarker, N. C.; Golzar Hussain, G. M.; Hardcastle, K. I.; Nordlander, E.; Rosenberg, E. Organometallics 2005, 24, 3315
63. Knight, M. J.; Allegretti, F.; Kröger, E. A.; Polcik, M.; Lamont, C. L. A.; Woodruff, D. P. Surf. Sci. 2008, 602, 2524
64. Wang, H.; Prins, R. J. Catal. 2009, 264, 31
65. Meille, V.; Schulz, E.; Lemaire, M.; Faure, R.; Vrinat, M. Tetrahedron 1996, 52, 3953
66. Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533
67. Joule, J. A.; Mills, K. Heterocyclic Chemistry; 4 th ed.; Blackwell Publishing: Ames, IA, 2000.
68. Stanislaus, A.; Marafi, A.; Rana, M. S. Catal. Today 2010, 153, 1
69. Fu, W.; Zhang, L.; Tang, T.; Ke, Q.; Wang, S.; Hu, J.; Fang, G.; Li, J.; Xiao, F.-S. J. Am. Chem. Soc. 2011, 133, 15346
70. Yu, K.; Li, H.; Watson, E. J.; Virkaitis, K. L.; Carpenter, G. B.; Sweigart, D. A. Organometallics 2001, 20, 3550
71. Baldovino-Medrano, V. G.; Giraldo, S. A.; Centeno, A. b. J. Mol. Catal. A: Chem. 2009, 301, 127
72. Mozingo, R.; Harris, S. A.; Wolf, D. E.; Hoffhine, C. E.; Easton, N. R.; Folkers, K. J. Am. Chem. Soc. 1945, 67, 2092
73. Rooney, J. J.; Gault, F. G.; Kemball, C. Proc. Chem. Soc. 1960, 407
74. Hruszkewycz, D. P.; Wu, J.; Green, J. C.; Hazari, N.; Schmeier, T. J. Organometallics 2011, 31, 470
75. Avent, A. G.; Frankland, A. D.; Hitchcock, P. B.; Lappert, M. F. Chem. Commun. 1996, 2433
76. A similar (deprotonated) tautomer and binding motif has been reported bound to a phosphido-palladium two-centered moiety: Braunstein, P.; Matt, D.; Dusausoy, Y.; Fischer, J. Organometallics 1983, 2, 1410
77. 6 octahedral compounds, but thermodynamic binding experiments have not been reported to the authors' knowledge. See: Mocella, C. J.; Delafuente, D. A.; Keane, J. M.; Warner, G. R.; Friedman, L. A.; Sabat, M.; Harman, W. D. Organometallics 2004, 23, 3772-3779
78. Caldwell, T. E.; Land, D. P. Polyhedron 1997, 16, 3197
79. Sexton, B. A. Surf. Sci. 1985, 163, 99
80. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165
81. Mecozzi, S.; West, A. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10566
82. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303
83. Gaussian 09, Revision C.01; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc.: Wallingford, CT, 2009.
84. Theoretical study of chemisorbed H on Pd surfaces suggests that formation of an H-Pd bond is accompanied by transfer of ca. 0.2 electrons from Pd to H. See: Tománek, D.; Sun, Z.; Louie, S. G. Phys. Rev. B 1991, 43, 4699-4713
85. Kurosawa, H. J. Organomet. Chem. 2004, 689, 4511