Gas-phase C-H and N-H bond activation by a high valent nitrido-iron dication and 〈NH〉-transfer to activated olefins

Journal of the American Chemical Society

Volumn 130, Issue 13, 2008, Pages 4285-4294

  Schlangen, Maria ^a   Neugebauer, Johannes ^b   Reiher, Markus ^b   Schröder, Detlef ^c   López, Jesús Pitarch ^a   Haryono, Marco ^a   Heinemann, Frank W ^d   Grohmann, Andreas ^a   Schwarz, Helmut ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b ETH ZURICH   (Switzerland)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^d UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; HYDROGEN BONDS; LIGANDS; NITROGEN; OLEFINS;

ACTIVATED OLEFINS; BOND ACTIVATION; NITRIDO-IRON DICATION;

IRON COMPOUNDS;

ALKENE DERIVATIVE; CARBON; CHELATING AGENT; HYDROGEN; IRON; IRON COMPLEX; ISOTOPE; LIGAND; NITROGEN; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; GAS; HYDROGEN BOND; ISOMER; MASS SPECTROMETRY; SYNTHESIS;

EID: 41549108484     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075617w     Document Type: Article

References (98)

1. Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348, 23.
2. +, see: (a) Buckner, S. W.; Freiser, B. S. J. Am. Chem. Soc. 1987, 109, 4715.
3. (b) Buckner, S. W.; Gord, J. R.; Freiser, B. S. J. Am. Chem. Soc. 1988, 110, 6606.
4. +, see: (a) Schröder, D.; Hrušák, J.; Schwarz, H. Ber. Bunsen. Phys. Chem. 1993, 97, 1085.
5. (b) Brönstrup, M.; Kretschmar, I.; Schröder, D.; Schwarz, H. Helv. Chim. Acta 1998, 81, 2348.
6. (c) Brönstrup, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1999, 5, 1176.
7. (d) Liyanage, R.; Griffin, J. B.; Armentrout, P. B. J. Chem. Phys. 2003, 119, 8979.
8. (e) Liyanage, R.; Armentrout, P. B. Int. J. Mass Spectrom. 2005, 241, 243.
9. See also: (a) Fiedler, A.; Iwata, S. Chem. Phys. Lett. 1997, 271, 143.
10. (b) Tan, L.; Liu, F. Y.; Armentrout, P. B. J. Chem. Phys. 2006, 124, 084302.
11. Martin, L. L.; Martin, R. L.; Sargeson, A. M. Polyhedron 1994, 13, 1969.
12. Berry, J. F.; Bill, E.; Bothe, E.; Neese, F.; Wieghardt, K. J. Am. Chem. Soc. 2006, 128, 13515.
13. Song, Y.-F.; Berry, J.; Bill, E.; Bothe, E.; Weyhermueller, T.; Wieghardt, K. Inorg. Chem. 2007, 46, 2208.
14. Behrens, H.; Wakamatsu, H. Z. Anorg. Allg. Chem. 1963, 320, 30.
15. (a) Marynick, D. S.; Kirkpatrick, C. M. J. Phys. Chem. 1983, 87, 3273.
16. (b) Kai, E.; Misawa, T.; Nishimoto, K. Bull. Chem. Soc. Jpn. 1980, 53, 2481.
17. Mosbæk, H.; Poulsen, K. G. Chem. Commun. 1969, 479.
18. Senoff, C. V. J. Chem. Educ. 1990, 67, 368.
19. Bolvin, H. Inorg. Chem. 2007, 46, 417.
20. Smith, P. L.; Chordia, M. D.; Harman, W. D. Tetrahedron 2001, 57, 8203.
21. Pitarch López, J.; Kämpf, H.; Grunert, M.; Gütlich, P.; Heinemann, F. W.; Prakash, R.; Grohmann, A. Chem. Commun. 2006, 1718.
22. Pitarch López, J.; Heinemann, F. W.; Prakash, R.; Hess, B. A.; Horner, O.; Jeandey, C.; Oddou, J.-L.; Latour, J.-M.; Grohmann, A. Chem. Eur. J. 2002, 8, 5709.
23. Pitarch López, J.; Heinemann, F. W.; Grohmann, A.; Horner, O.; Latour, J.-M.; Ramachandraiah, G. Inorg. Chem. Commun. 2004, 7, 773.
24. For a recent review on magnetic spin transitions, see: Sato, O.; Tao, J.; Zhang, Y.-Z. Angew. Chem., Int. Ed. 2007, 46, 2152.
25. Meyer, K.; Bill, E.; Mienert, B.; Weyhermüller, T.; Wieghardt, K. J. Am. Chem. Soc 1999, 121, 4859.
26. (a) Aliaga-Alcalde, N.; DeBeer George, S.; Mienert, B.; Bill, E.; Wieghardt, K.; Neese, F. Angew. Chem., Int. Ed. 2005, 44, 2908.
27. (b) Petrenko, T.; et al. J. Am. Chem. Soc. 2007, 129, 11053.
28. Berry, J. F.; Bill, E.; Bothe, E.; DeBeer-George, S.; Mienert, B.; Neese, F.; Wieghardt, K. Science 2006, 312, 1937.
29. Chirik, P. J. Angew. Chem., Int. Ed. 2006, 45, 6956.
30. Schröder, D.; Schwarz, H.; Aliaga-Alcalde, N.; Neese, F. Eur. J. Inorg. Chem. 2007, 6, 816.
31. Schröder, D.; Weiske, T.; Schwarz, H. Int. J. Mass Spectrom. 2002, 219, 729.
32. (a) Schröder, D.; Schwarz, H.; Schenk, S.; Anders, E. Angew. Chem., Int. Ed. 2003, 42, 5087.
33. (b) Roithová, J.; Hrušák, J.; Schröder, D.; Schwarz, H. Inorg. Chim. Acta 2005, 358, 4287.
34. (c) Feyel, S.; Schröder, D.; Schwarz, H. J. Phys. Chem. A 2006, 110, 2647.
35. (d) Schröder, D.; Engeser, M.; Schwarz, H.; Rosenthal, E. C. E.; Döbler, J.; Sauer, J. Inorg. Chem. 2006, 45, 6235.
36. (e) Schröder, D.; Roithová, J.; Schwarz, H. Int. J. Mass Spectrom. 2006, 254, 197.
37. Schröder, D.; Semialjac, M.; Schwarz, H. Int. J. Mass Spectrom. 2004, 233, 103.
38. Bouchoux, G.; Leblanc, D.; Salpin, J. Y. Int. J. Mass Spectrom. 1996, 153, 37.
39. Schröder, D.; Engeser, M.; Brönstrup, M.; Daniel, C.; Spandl, J.; Hartl, H. Int. J. Mass Spectrom. 2003, 228, 743.
40. (a) Trage, C.; Diefenbach, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 2006, 12, 2454.
41. (b) Gruene, P.; Trage, C.; Schröder, D.; Schwarz, H. Eur. J. Inorg. Chem. 2006, 2006, 4546.
42. Jagoda-Cwiklik, B.; Jungwirth, P.; Rulišek, L.; Milko, P.; Roithová, J.; Lematre, J.; Maitre, P.; Ortega, J. M.; Schröder, D. ChemPhysChem 2007, 8, 1629.
43. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
44. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
45. (a) Eichkorn, K.; Treutier, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283.
46. (b) Eichkorn, K.; Weigend, F.; Treutier, O.; Ahlrichs, R. Theor. Chem. Acc. 1997, 97, 119.
47. (a) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
48. (b) Dunlap, B. I.; Connolly, J. W. D.; Sabin, J. R. J. Chem. Phys. 1979, 71, 3396.
49. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
50. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165.
51. (a) Reiher, M.; Hess, B. A. Chem. Eur. J. 2002, 8, 5332.
52. (b) Schatz, M.; Raab, V.; Foxon, S. P.; Brehm, G.; Schneider, S.; Reiher, M.; Holthausen, M.; Sundermeyer, J.; Schindler, S. Angew. Chem., Int. Ed. 2004, 43, 4360.
53. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, Germany, 2000.
54. Reiher, M.; Salomon, O.; Hess, B. A. Theor. Chem. Acc. 2001, 107, 48.
55. Salomon, O.; Reiher, M.; Hess, B. A. J. Chem. Phys. 2002, 117, 4729.
56. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
57. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
58. Neugebauer, J.; Reiher, M.; Kind, C.; Hess, B. A. J. Comput. Chem. 2002, 23, 895.
59. Grapperhaus, C. A.; Mienert, B.; Bill, E.; Weyhermüller, T.; Wieghardt, K. Inorg. Chem. 2000, 39, 5306.
60. Calculated with the Chemputer program developed by M. Winter, University of Sheffield; http://winter.group.shef.ac.uk/chemputer/.
61. (a) Levsen, K. Fundamental Aspects of Organic Mass Spectrometry; VCH: Weinheim, Germany, 1978.
62. (b) Gross, J. H. Mass Spectrometry: A Textbook; Springer-Verlag: Berlin, 2004.
63. (a) Schröder, D.; Fiedler, A.; Hrušák, J.; Schwarz, H. J. Am. Chem. Soc. 1992, 114, 1215.
64. (b) Schwarz, J.; Wesendrup, R.; Schröder, D.; Schwarz, H. Chem. Ber. 1996, 129, 1463.
65. For selected examples, see: (a) Alcami, M.; Mó, O.; Yañez, M. Mass Spectrom. Rev. 2001, 20, 195.
66. (b) Schwarz, H. Int. J. Mass Spectrom. 2004, 237, 75.
67. (c) Mercero, J. M.; Matxain, J. M.; Lopez, X.; York, D. M.; Largo, A.; Erikson, L. A.; Ugalde, J. M. Int. J. Mass Spectrom. 2005, 240, 37.
68. (d) The entire Vol. 201 of Int. J. Mass Spectrom. is dedicated to computational studies of ionic systems, see: Koch, W.; Hase, W. L. Int. J. Mass Spectrom. 2000, 201, 1.
69. -1) which may be regarded as a minimal estimate for the uncertainty of the computational predictions for the system under study.
70. Schröder, D.; Holthausen, M. C.; Schwarz, H. J. Phys. Chem. B 2004, 108, 14407.
71. Note that for all structures, except for 8, 10, 13, and 14, the BP86 and B3LYP functionals predict the same multiplicity of the ground state.
72. In a parent-ion scan, a first analyzer scans a regular mass spectrum, then the reaction of interest is allowed to occur in an intermediate collision cell, while a second mass analyzer is fixed to the mass of the desired product ion. In this way, all ions ("parents") giving rise to a particular product ion can be identified; for an example, see ref 24a.
73. van Verth, J. E.; Saunders, W. H.; Kermis, T. W. Can. J. Chem. 1998, 76, 821.
74. For the related diaminomethane, also see: DeBons, F. E.; Loudon, G. M. J. Org. Chem. 1980, 45, 1703.
75. +.
76. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
77. Roithová, J.; Herman, Z.; Schröder, D.; Schwarz, H. Chem. Eur. J. 2006, 12, 2465.
78. + fragment (ratio 1.2:1), which is a typical observation for charge-separation reactions of multiply charged ions to fragments of largely different masses and is due to differential collection efficiencies of the fragments formed upon Coulomb explosion in a beam-type mass spectrometer. See, for example: (a) Schröder, D.; Schroeter, K.; Schwarz, H. Int. J. Mass Spectrom. 2001, 212, 327.
79. (b) Tsierkezos, N.; Schröder, D.; Schwarz, H. J. Phys. Chem. A 2003, 107, 9575.
80. (c) Roithová, J.; Milko, P.; Ricketts, C. L.; Schröder, D.; Besson, T.; Dekoj, V.; Bělohradský, M. J. Am. Chem. Soc. 2007, 129, 10141.
81. (a) Jackson, T. C.; Jacobsen, D. B.; Freiser, B. S. J. Am. Chem. Soc. 1984, 106, 1252.
82. (b) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1433.
83. Reviews on metal-oxide ions: (a) Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1973.
84. (b) Schröder, D.; Shaik, S.; Schwarz, H. Struct. Bond. 2000, 57, 91.
85. (c) Schröder, D.; Schwarz, H. Top. Organomet. Chem. 2007, 22, 1.
86. Feyel, S.; Schröder, D.; Rozanska, X.; Sauer, J.; Schwarz, H. Angew. Chem., Int. Ed. 2006, 45, 4677.
87. Roithová, J.; Schröder, D. Phys. Chem. Chem. Phys. 2007, 9, 2341.
88. NIST Standard Reference Database Number 69, Gaithersburg, MD, 2005, http://webbook.nist.gov/chemistry/.
89. Neutralization-reionization mass spectrometry has been used to characterize the organic products formed in metal-mediated reactions in the gas phase, see: (a) Schröder, D.; Sülzle, D.; Hrušák, J.; Böhme, D. K.; Schwarz, H. Int. J. Mass Spectrom. Ion Processes 1991, 110, 145.
90. (b) Schröder, D.; Schwarz, H. Helv. Chim. Acta 1992, 75, 1281.
91. Schröder, D.; Schwarz, H. J. Organomet. Chem. 1995, 504, 123.
92. Sievers, M. R.; Jarvis, L. M.; Armentrout, P. B. J. Am. Chem. Soc. 1998, 120, 1891.
93. Walter, D.; Armentrout, P. B. J. Am. Chem. Soc. 1998, 120, 3176.
94. Schroeter, K.; Schalley, C. A.; Schröder, D.; Schwarz, H. Organometallics 1997, 16, 986.
95. (a) Schröder, D.; Schwarz, H.; Milko, P.; Roithová, J. J. Phys. Chem. A 2006, 110, 8346.
96. (b) Feyel, S.; Schwarz, H.; Schröder, D.; Daniel, C.; Hartl, H.; Döbler, J.; Sauer, J.; Santambrogio, G.; Wöste, L.; Asmis, K. ChemPhysChem 2007, 8, 1640.
97. (a) Dopfer, O. J. Phys. Org. Chem. 2006, 19, 540.
98. (b) Polfer, N. C.; Oomens, J. Phys. Chem. Chem. Phys. 2006, 9, 3804.