Gas-phase activation of methane by ligated transition-metal cations

Proceedings of the National Academy of Sciences of the United States of America

Volumn 105, Issue 47, 2008, Pages 18114-18119

  Schröder, Detlef ^a   Schwarz, Helmut ^b  

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

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Bond activation; Kinetic isotope effects; Mass spectrometry

Indexed keywords

CHLORINE; FLUORINE; ISOTOPE; METAL ION; METHANE; OXYGEN; TRANSITION ELEMENT;

CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMISTRY; GAS; MASS SPECTROMETRY; OXIDATION; PRIORITY JOURNAL; REVIEW;

EID: 57449117883     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0801849105     Document Type: Review

References (92)

1. Olah GA, Goeppert A, Prakash GKS (2006) Beyond Oil and Gas: The Methanol Economy (Wiley-VCH, Weinheim, Germany).
2. Irikura KK, Beauchamp JL (1991) Methane oligomerization in the gas phase by 3rd-row transition metal ions. J Am Chem Soc 113:2769-2770.
3. Irikura KK, Beauchamp JL (1991) Electronic-structure considerations for methane activation by 3rd-row transition-metal ions. Phys Chem 95:8344-8351.
4. + mediated oxidation of methane by molecular oxygen in the gas phase. Angew Chem Int Ed Engl 33:1174-1176.
5. +-catalyzed oxidation of methane: Theory and experiment. J Phys Chem A 101:1567-1579.
6. Wesendrup R, Schwarz H (1995) Tantalum-mediated coupling of methane and carbon dioxide in the gas phase. Angew Chem Int Ed Engl 34:2033-2035.
7. +-mediated coupling of carbon dioxide with methane. Organometallics 17:2344-2351.
8. Chiodo S, (2006) Activation of methane by the iron dimer cation. A theoretical study. J Phys Chem A 110:12501-12511.
9. + and the thermochemistry of Ni-ligand complexes. Phys Chem Chem Phys 7:1054-1064.
10. + and the thermochemistry of Zr-ligand complexes. J Phys Chem A 107:4396-4406.
11. + with methane. Int J Mass Spectrom 254:168-182.
12. +, and the thermochemistry of Mo-ligand complexes. J Phys Chem A 110:8327-8338.
13. Parke LG, Hinton CS, Armentrout PB (2007) Experimental and theoretical studies of the activation of methane by Ta. J Phys Chem C 111:17773-17787.
14. +. J Phys Chem A 110:1242-1260.
15. + with methane. J Phys Chem A 108:9660-9672.
16. +. Int J Mass Spectrom 255/256:279-300.
17. Li F-X, Armentrout PB (2006) Activation of methane by gold cations: Guided ion beam and theoretical studies. J Chem Phys 125: Art. No. 133114.
18. Roth LM, Freiser BS (1991) Gas-phase chemistry and photochemistry of doubly charged transition-metal containing ions. Mass Spectrom Rev 10:303-328.
19. + in the gas phase. Organometallics 16:210-224.
20. 2+ with small alkanes. J. Phys Chem 95:7721-7726.
21. x (x = 0-3) bond energies and reaction mechanisms. J Chem Phys 115:9747-9763.
22. x (x = 0-3) complexes. J Chem Phys 121:10976-10990.
23. Schröder D, Eller K, Prüsse T, Schwarz H (1991) Ligand-enhanced selectivity in the CH/CC bond activation of ketones by iron(I) ions in the gas phase. Organometallics 10:2052-2057.
24. Schröder D, Schwarz H (1995) Ligand effects as a probe for remote C-H bond activation by metal cations in the gas phase. J Organomet Chem 504:123-138.
25. Tjelta BL, Armentrout PB (1996) Ligand effects in C-H and C-C bond activation by gas-phase transition metalligand complexes. J Am Chem Soc 118:9652-9660.
26. Albert G, et al. (1997) Methane activation by rhodium cluster argon complexes. Chem Phys Lett 268:235-244.
27. Achatz U, et al. (1999) The platinum hydride-methyl complex: A frozen reaction intermediate? J Phys Chem A 103:8200-8206.
28. + (M = Cu, Ag, Au). J Phys Chem 100:12253-12260.
29. Schlangen M, Schröder D, Schwarz H (2007) Pronounced ligand effects on the nickel-mediated thermal activation of methane. Angew Chem Int Ed 46:1641-1644.
30. 6 couple. Helv Chim Acta 90:847-853.
31. 2] complexes. Inorg Chem 33:5094-5100.
32. + Angew Chem Int Ed Engl 34:2517-2520.
33. + in the gas phase: Structure, electronic states, and the reactivity with hydrogen and hydrocarbons. J Am Chem Soc 118:9941-9952.
34. Beyer MK, et al. (2001) Corroding the chromium cation. Mol Phys Chem 99:699-702.
35. 3+ - A thermochemically stable diatomic trication with a covalent bond. Angew Chem Int Ed Engl 38:137-140.
36. + and their reactivity with small alkanes. J Am Chem Soc 108:6197-6202.
37. +, n = 0-4) in the gas phase. Coll Czech Chem Comm 63:1498-1512.
38. Roithová J, Schröder D (2007) Bimolecular reactions of molecular dications: New reactivity paradigms and bond-forming processes. Phys Chem Chem Phys 9:2341-2349.
39. + in the gas phase. Ber Bunsenges Phys Chem 97:1085-1090.
40. 9). Chem Eur J 13:6810-6816.
41. + (X = H, Cl, Br, CHO). Can J Chem 83:1936-1940.
42. +) with hydrocarbons. J Am Chem Soc 105:6320-6321.
43. +. J Am Chem Soc 106:2543-2549, 1984.
44. + (M = Fe, Co, and Ni): A combined mass spectrometric and DFT study. J Phys Chem A 108:9755-9761.
45. +: The same and not the same. Angew Chem Int Ed Engl 46:5614-5617.
46. Schröder D, Schwarz H (1995) C-H and C-C bond activation by ionic transition-metal oxides in the gas phase. Angew Chem Int Ed Engl 34:1973-1995.
47. Schröder D, Shaik S, Schwarz H (2000) Characterization, orbital description, and reactivity patterns of transition-metal oxo species in the gas phase. Struct Bond 97:91-123.
48. Schröder D, Schwarz H (2007) Intrinsic mechanisms of oxidation reactions as revealed by gas-phase experiments. Top Organomet Chem 22:1-15.
49. Schröder D, Shaik S, Schwarz H (2000) Intrinsic mechanisms of oxidation reactions as revealed by gas-phase experiments. Acc Chem Res 33:139-145.
50. Shaik S, Hirao H, Kumar D (2007) Reactivity of high-valent iron-oxo species in enzymes and synthetic reagents: A tale of many states. Acc Chem Res 40:532-542.
51. Ryan MF, Fiedler A, Schröder D, Schwarz H (1995) Radical-like behavior of manganese oxide cation in its gas-phase reactions with dihydrogen and alkanes. J Am Chem Soc 117:2033-2040.
52. + activates methane. Angew Chem Int Ed Engl 29:1433-1434.
53. + in the gas phase as studied by multiple mass-spectrometric techniques. Int J Mass Spectrom Ion Processes 161:175-191.
54. + and water. J Phys Chem 98:68-70.
55. Irikura KK, Beauchamp JL (1989) Osmium-tetroxide and its fragment ions in the gas phase - Reactivity with hydrocarbons and small molecules. J Am Chem Soc 111:75-85.
56. + (n = 1-4) with methane. Organometallics 23:3656-3667.
57. Schwarz H (2003) Relativistic effects in gas-phase ion chemistry: An experimentalist's view. Angew Chem Int Ed Engl 42:4442-4454.
58. Rivalta I, Russo N, Sicilia E (2006) Methane activation by chromium oxide cations in the gas phase: A theoretical study. J Comp Chem 27:174-187.
59. + in the gas phase - the role of iron oxidation state in C-H activations. Angew Chem Int Ed Engl 30:991-993.
60. Kretzschmar I, Fiedler A, Harvey JN, Schröder D, Schwarz H (1997) Effects of sequential ligation of molybdenum cation by chalcogenides on electronic structures and gas-phase reactivity. J Phys Chem A 101:6252-6264.
61. Brönstrup M, Schröder D, Kretzschmar I, Schwarz H, Harvey JN (2001) Platinum dioxide cation: Easy to generate experimentally but difficult to describe theoretically. J Am Chem Soc 123:142-147.
62. + cations: It also works without a transition metal! Angew Chem Int Ed 45:5705-5708.
63. Brönstrup M, Kretzschmar I, Schröder D, Schwarz H (1998) Iron-mediated amination of hydrocarbons in the gas phase. Helv Chim Acta 81:2348-2369.
64. + by C-F activation in the gas phase and evaluation of thermochemical data. Helv Chim Acta 75:2215-2218.
65. + in the gas phase. Helv Chim Acta 75:1281-1286.
66. + isomers relevant for the oxygenation of aromatic hydrocarbons. J Am Chem Soc 116:1096-1100.
67. + complexes (L = benzene, pyridine, naphthalene). Liebigs Ann 429-431.
68. +. J Phys Chem B 108:14407-14416.
69. + complexes (L = pyridine, bipyridine, and phenanthroline). Z Naturf B 62b:309-313.
70. 2O. Angew Chem Int Ed Engl 29:1431-1433, 1990.
71. + with benzene. Int J Mass Spectrom 203:155-163.
72. Schröder D, Schwarz H, Aliaga-Alcalde N, Neese F (2007) Fragmentation of the (cyclam-acetato) ironazide cation in the gas phase. Eur J Inorg Chem 6:816-821.
73. +]: A genuine iron(V) species with a ground-state spin S = 1/2. Angew Chem Int Ed 44:2908-2912.
74. Schlangen M, et al. (2008) Gas phase C-H and N-H bond activation by a high valent nitrido-iron dication and 〈NH〉-transfer to activated olefins. J Am Chem Soc 130:4285-4294.
75. +: From a "Holy Grail" to an achievable goal? Angew Chem Int Ed 45:4681-4685.
76. + (x = 3, 4, 5): The role of oxygen-centered radicals in thermal hydrogen-atom abstraction. Angew Chem Int Ed 47:1946-1950.
77. + with M = Cu, Ag, Au and X = H, D. Organometallics 19:2608-2615.
78. Derrick PJ (1985) Isotope Effects in Fragmentation. Mass Spectrom Rev 2:285-298.
79. +-mediated activation of methane - Theory and experiment. Chem Phys Lett 239:75-83, 1995.
80. 4 with O(D-1) and OH: New laboratory measurements and their implications for the isotopic composition of stratospheric methane. J Geophys Res Atmos 106:23127-23138.
81. +. J Am Chem Soc 122:12317-12326.
82. + isomers. J Am Chem Soc 114:1215-1222.
83. +. J Chem Phys 116:4071-4078.
84. +. J Chem Phys 118:5872-5879, .
85. Schwarz H (2004) On the spin-forbiddeness of gasphase ion-molecule reactions: A fruitful intersection of experimental and computational studies. Int J Mass Spectrom 237:75-105.
86. Harvey JN, Poli R, Smith KM (2003) Understanding the reactivity of transition metal complexes involving multiple spin states. Coord Chem Rev 238:347-361.
87. Böhme DK, Schwarz H (2005) Gas-phase catalysis by atomic and cluster metal ions: The ultimate single-site catalysts. Angew Chem Int Ed 44:2336-2354.
88. Shilov AE (1984) Activation of Saturated Hydrocarbons by Transition Metal Complexes (Reidel, Dordrecht, The Netherlands).
89. Periana RA, et al. (1998) Platinum catalysts for the high-yield oxidation of methane to a methanol derivative. Science 280:560-564.
90. Labinger JA, Bercaw JE (2002) Understanding and exploiting C-H bond activation. Nature 417:507-514.
91. Labinger JA (2004) Selective alkane oxidation: Hot and cold approaches to a hot problem. J Mol Catal 220:27-35.
92. Lersch M, Tilset M (2005) Mechanistic aspects of C-H activation by Pt complexes. Chem Rev 105:2471-2526.