Iron dicarbonyl complexes featuring bipyridine-based PNN pincer ligands with short interpyridine C-C bond lengths: Innocent or non-innocent ligand?

Chemistry - A European Journal

Volumn 20, Issue 15, 2014, Pages 4403-4413

  Zell, Thomas ^a   Milko, Petr ^a   Fillman, Kathlyn L ^b   Diskin Posner, Yael ^a   Bendikov, Tatyana ^a   Iron, Mark A ^a   Leitus, Gregory ^a   Ben David, Yehoshoa ^a   Neidig, Michael L ^b   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b UNIVERSITY OF ROCHESTER   (United States)

Author keywords

bipyridine; iron; pi interactions; pincer ligands; redox chemistry

Indexed keywords

BOND LENGTH; CHLORINE COMPOUNDS; COVALENT BONDS; CYCLIC VOLTAMMETRY; FREE RADICAL REACTIONS; IRON; IRON COMPOUNDS; METAL COMPLEXES; MOLYBDENUM COMPOUNDS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

ANTIFERRO-MAGNETICALLY COUPLED; BIPYRIDINES; INTRA-MOLECULAR ELECTRON TRANSFER; MULTINUCLEAR NMR SPECTROSCOPY; PI INTERACTIONS; PINCER LIGANDS; REDOX CHEMISTRY; SINGLE CRYSTAL X-RAY DIFFRACTION;

LIGANDS;

EID: 84897977678     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201304631     Document Type: Article

References (119)

1. K. Hindson, B. de Bruin, Eur. J. Inorg. Chem. 2012, 340-342
2. H. Grützmacher, Angew. Chem. 2008, 120, 1838-1842
3. Angew. Chem. Int. Ed. 2008, 47, 1814-1818.
4. W. I. Dzik, J. I. van der Vlugt, J. N. H. Reek, B. de Bruin, Angew. Chem. 2011, 123, 3416-3418
5. Angew. Chem. Int. Ed. 2011, 50, 3356-3358
6. W. Kaim, Inorg. Chem. 2011, 50, 9752-9765
7. J. I. van der Vlugt, Eur. J. Inorg. Chem. 2012, 363-375
8. P. J. Chirik, K. Wieghardt, Science 2010, 327, 794-795
9. O. R. Luca, R. H. Crabtree, Chem. Soc. Rev. 2013, 42, 1440-1459
10. V. K. K. Praneeth, M. R. Ringenberg, T. R. Ward, Angew. Chem. Int. Ed. 2012, 51, 10228-10234
11. K. G. Caulton, Eur. J. Inorg. Chem. 2012, 435-443
12. W. Kaim, Eur. J. Inorg. Chem. 2012, 343-348
13. S. Blanchard, E. Derat, M. Desage-El Murr, L. Fensterbank, M. Malacria, V. Mouriès-Mansuy, Eur. J. Inorg. Chem. 2012, 376-389
14. K. Ray, T. Petrenko, K. Wieghardt, F. Neese, Dalton Trans. 2007, 1552-1566
15. D. Sieh, M. Schlimm, L. Andernach, F. Angersbach, S. Nückel, J. Schöffel, N. Šušnjar, P. Burger, Eur. J. Inorg. Chem. 2012, 444-462
16. V. Lyaskovskyy, B. de Bruin, ACS Catal. 2012, 2, 270-279
17. A. I. O. Suarez, V. Lyaskovskyy, J. N. H. Reek, J. I. van der Vlugt, B. de Bruin, Angew. Chem. 2013, 125, 12740-12760
18. Angew. Chem. Int. Ed. 2013, 52, 12510-12529.
19. B. L. Small, M. Brookhart, A. M. A. Bennett, J. Am. Chem. Soc. 1998, 120, 4049-4050
20. B. L. Small, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 7143-7144.
21. G. J. P. Britovsek, V. C. Gibson, S. J. McTavish, G. A. Solan, A. J. P. White, D. J. Williams, G. J. P. Britovsek, B. S. Kimberley, P. J. Maddox, Chem. Commun. 1998, 849-850
22. G. J. P. Britovsek, M. Bruce, V. C. Gibson, B. S. Kimberley, P. J. Maddox, S. Mastroianni, S. J. McTavish, C. Redshaw, G. A. Solan, S. Strömberg, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 8728-8740.
23. S. C. Bart, E. Lobkovsky, P. J. Chirik, J. Am. Chem. Soc. 2004, 126, 13794-13807
24. R. J. Trovitch, E. Lobkovsky, E. Bill, P. J. Chirik, Organometallics 2008, 27, 1470-1478
25. S. K. Russell, J. M. Darmon, E. Lobkovsky, P. J. Chirik, Inorg. Chem. 2010, 49, 2782-2792
26. S. C. Bart, E. Lobkovsky, E. Bill, P. J. Chirik, J. Am. Chem. Soc. 2006, 128, 5302-5303.
27. A. M. Tondreau, E. Lobkovsky, P. J. Chirik, Org. Lett. 2008, 10, 2789-2792
28. A. M. Tondreau, J. M. Darmon, B. M. Wile, S. K. Floyd, E. Lobkovsky, P. J. Chirik, Organometallics 2009, 28, 3928-3940
29. A. M. Tondreau, C. C. H. Atienza, J. M. Darmon, C. Milsmann, H. M. Hoyt, K. J. Weller, S. A. Nye, K. M. Lewis, J. Boyer, J. G. P. Delis, E. Lobkovsky, P. J. Chirik, Organometallics 2012, 31, 4886-4893
30. S. K. Russell, C. Milsmann, E. Lobkovsky, T. Weyhermüller, P. J. Chirik, Inorg. Chem. 2011, 50, 3159-3169
31. A. M. Tondreau, C. C. H. Atienza, K. J. Weller, S. A. Nye, K. M. Lewis, J. G. P. Delis, P. J. Chirik, Science 2012, 335, 567-570.
32. J. V. Obligacion, P. J. Chirik, Org. Lett. 2013, 15, 2680-2683.
33. K. T. Sylvester, P. J. Chirik, J. Am. Chem. Soc. 2009, 131, 8772-8774
34. J. M. Hoyt, K. T. Sylvester, S. P. Semproni, P. J. Chirik, J. Am. Chem. Soc. 2013, 135, 4862-4877.
35. J. Y. Wu, B. N. Stanzl, T. Ritter, J. Am. Chem. Soc. 2010, 132, 13214-13216.
36. J. Y. Wu, B. t. Moreau, T. Ritter, J. Am. Chem. Soc. 2009, 131, 12915-12917.
37. B. t. Moreau, J. Y. Wu, T. Ritter, Org. Lett. 2009, 11, 337-339.
38. J. Raynaud, J. Y. Wu, T. Ritter, Angew. Chem. 2012, 124, 11975-11978
39. Angew. Chem. Int. Ed. 2012, 51, 11805-11808; corrigendum
40. J. Raynaud, J. Y. Wu, T. Ritter, Angew. Chem. 2012, 124, 13095
41. Angew. Chem. Int. Ed. 2012, 51, 12920.
42. P. L. Holland, Dalton Trans. 2010, 39, 5415-5425
43. S. N. Brown, Inorg. Chem. 2012, 51, 1251-1260
44. A. Das, T. M. Scherer, S. M. Mobin, W. Kaim, G. K. Lahiri, Chem. Eur. J. 2012, 18, 11007-11018
45. P. Chaudhuri, C. N. Verani, E. Bill, E. Bothe, T. Weyhermüller, K. Wieghardt, J. Am. Chem. Soc. 2001, 123, 2213-2223.
46. C. C. Scarborough, K. Wieghardt, Inorg. Chem. 2011, 50, 9773-9793.
47. C. Gunanathan, D. Milstein, Top. Organomet. Chem. 2011, 37, 55-84
48. D. Milstein, Top. Catal. 2010, 53, 915-923
49. C. Gunanathan, D. Milstein, Science 2013, 341, 1229712.
50. E. Balaraman, C. Gunanathan, J. Zhang, L. J. W. Shimon, D. Milstein, Nat. Chem. 2011, 3, 609-614
51. E. Balaraman, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 11906-11909
52. Angew. Chem. Int. Ed. 2011, 50, 11702-11705
53. E. Balaraman, B. Gnanaprakasam, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2010, 132, 16756-16758
54. D. Srimani, M. Feller, Y. Ben-David, D. Milstein, Chem. Commun. 2012, 48, 11853-11855
55. E. Balaraman, E. Fogler, D. Milstein, Chem. Commun. 2012, 48, 1111-1113.
56. D. Srimani, E. Balaraman, B. Gnanaprakasam, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2012, 354, 2403-2406
57. D. Srimani, Y. Ben-David, D. Milstein, Angew. Chem. 2013, 125, 4104-4107
58. Angew. Chem. Int. Ed. 2013, 52, 4012-4015
59. D. Srimani, Y. Ben-David, D. Milstein, Chem. Commun. 2013, 49, 6632-6634.
60. E. Balaraman, E. Khaskin, G. Leitus, D. Milstein, Nat. Chem. 2013, 5, 122-125.
61. E. Khaskin, D. Milstein, ACS Catal. 2013, 3, 448-452.
62. S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367
63. Angew. Chem. Int. Ed. 2008, 47, 3317-3321
64. K. Gopalaiah, Chem. Rev. 2013, 113, 3248-3296
65. M. Darwish, M. Wills, Catal. Sci. Technol. 2012, 2, 243-255
66. K. Junge, K. Schröder, M. Beller, Chem. Commun. 2011, 47, 4849-4859
67. S. Gaillard, J.-L. Renaud, ChemSusChem 2008, 1, 505-509
68. R. H. Morris, Chem. Soc. Rev. 2009, 38, 2282-2291
69. S. Chakraborty, H. Guan, Dalton Trans. 2010, 39, 7427-7436
70. H. Nakazawa, M. Itazaki, in Top. Organomet. Chem. 2011, 33, 27-81.
71. R. Langer, Y. Diskin-Posner, G. Leitus, L. J. W. Shimon, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 10122-10126
72. Angew. Chem. Int. Ed. 2011, 50, 9948-9952.
73. T. Zell, B. Butschke, Y. Ben-David, D. Milstein, Chem. Eur. J. 2013, 19, 8068-8072.
74. R. Langer, G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 2168-2172
75. Angew. Chem. Int. Ed. 2011, 50, 2120-2124.
76. R. Langer, M. A. Iron, L. Konstantinovski, Y. Diskin-Posner, G. Leitus, Y. Ben-David, D. Milstein, Chem. Eur. J. 2012, 18, 7196-7209.
77. D. Srimani, Y. Diskin-Posner, Y. Ben-David, D. Milstein, Angew. Chem. 2013, 125, 14381-14384
78. Angew. Chem. Int. Ed. 2013, 52, 14131-14134.
79. T. Zell, R. Langer, M. A. Iron, L. Konstantinovski, L. J. W. Shimon, Y. Diskin-Posner, G. Leitus, E. Balaraman, Y. Ben-David, D. Milstein, Inorg. Chem. 2013, 52, 9636-9649.
80. L. Zhang, D. Peng, X. Leng, Z. Huang, Angew. Chem. 2013, 125, 3764-3768
81. Angew. Chem. Int. Ed. 2013, 52, 3676-3680.
82. D. F. Evans, J. Chem. Soc. 1959, 2003-2005.
83. E. M. Pelczar, T. J. Emge, K. Krogh-Jespersen, A. S. Goldman, Organometallics 2008, 27, 5759-5767.
84. M. Wang, J. England, T. Weyhermuller, S. L. Kokatam, C. J. Pollock, S. DeBeer, J. Shen, G. P. Yap, K. H. Theopold, K. Wieghardt, Inorg. Chem. 2013, 52, 4472-4487
85. C. C. Scarborough, S. Sproules, T. Weyhermüller, S. DeBeer, K. Wieghardt, Inorg. Chem. 2011, 50, 12446-12462
86. M. Irwin, L. R. Doyle, T. Krämer, R. Herchel, J. E. McGrady, J. M. Goicoechea, Inorg. Chem. 2012, 51, 12301-12312
87. C. C. Scarborough, S. Sproules, C. J. Doonan, K. S. Hagen, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 2012, 51, 6969-6982
88. A. C. Bowman, J. England, S. Sproules, T. Weyhermüller, K. Wieghardt, Inorg. Chem. 2013, 52, 2242-2256
89. J. England, K. Wieghardt, Inorg. Chem. 2013, 52, 10067-10079
90. M. Wang, T. Weyhermuller, J. England, K. Wieghardt, Inorg. Chem. 2013, 52, 12763-12776.
91. M. H. Chisholm, J. C. Huffman, I. P. Rothwell, P. G. Bradley, N. Kress, W. H. Woodruff, J. Am. Chem. Soc. 1981, 103, 4945-4947.
92. E. Gore-Randall, M. Irwin, M. S. Denning, J. M. Goicoechea, Inorg. Chem. 2009, 48, 8304-8316.
93. H. Bock, J.-M. Lehn, J. Pauls, S. Holl, V. Krenzel, Angew. Chem. 1999, 111, 1004-1008
94. Angew. Chem. Int. Ed. 1999, 38, 952-955.
95. D. Benito-Garagorri, L. G. a. Alves, M. Puchberger, K. Mereiter, L. F. Veiros, M. J. Calhorda, M. D. Carvalho, L. P. Ferreira, M. Godinho, K. Kirchner, Organometallics 2009, 28, 6902-6914.
96. P. Brant, R. D. Feltham, J. Electron Spectrosc. Relat. Phenom. 1983, 32, 205-221
97. A. P. Grosvenor, B. A. Kobe, M. C. Biesinger, N. S. McIntyre, Surf. Interface Anal. 2004, 36, 1564-1574.
98. D. Briggs, P. Seah, Practical Surface Analysis: Auger and X-ray Photoelectron Spectroscopy, Wiley, Chichester (UK), 1990.
99. P. Brant, R. D. Feltham, Inorg. Chem. 1980, 19, 2673-2676
100. R. D. Feltham, P. Brant, J. Am. Chem. Soc. 1982, 104, 641-645
101. J. Blomquist, P. Kjäll, B. Folkesson, R. Larsson, Struct. Chem. 1991, 2, 223-229
102. J. Blomquist, U. Helgeson, B. Folkesson, R. Larsson, Chem. Phys. 1983, 76, 71-78.
103. For a comprehensive study evaluating the use of different methods for the description of bipyridine ligands in potentially redox non-innocent metal complexes see:, P. Milko, M. A. Iron, J. Chem. Theory Comput. 2014, 10, 220-235.
104. G. Beamson, D. Briggs, High-Resolution XPS of Organic Polymers: The Scienta ESCA 300 Database, Wiley, Chichester (UK), 1992.
105. Gaussian 09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Wallingford CT, 2009.
106. Y. Zhao, D. Truhlar, Theor. Chem. Acc. 2008, 120, 215-241.
107. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
108. C. Gunanathan, B. Gnanaprakasam, M. A. Iron, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2010, 132, 14763-14765.
109. T. H. Dunning Jr., P. J. Hay, in Modern Theoretical Chemistry, Vol. 3 (Ed.:, H. F. Schaefer III,), Plenum, New York, 1976, pp. 1-28.
110. M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1993, 85, 441-450.
111. F. Neese, WIREs Comput. Mol. Sci. 2012, 2, 73-78.
112. C. Møller, M. S. Plesset, Phys. Rev. 1934, 46, 618-622.
113. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
114. F. Neese, F. Wennmohs, A. Hansen, U. Becker, Chem. Phys. 2009, 356, 98-109
115. S. Kossmann, F. Neese, Chem. Phys. Lett. 2009, 481, 240-243
116. R. Izsak, F. Neese, J. Chem. Phys. 2011, 135, 144105.
117. F. Neese, J. Comput. Chem. 2003, 24, 1740-1747, and references therein.
118. C. Angeli, R. Cimiraglia, J.-P. Malrieu, J. Chem. Phys. 2002, 117, 9138-9153, and references therein.
119. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, C. R. Landis, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin, Madison, 2013.