Probing the reactivity of oxomanganese-salen complexes: An electrospray tandem mass spectrometric study of highly reactive intermediates

Chemistry - A European Journal

Volumn 7, Issue 3, 2001, Pages 591-599

  Feichtinger, Derek ^a   Plattner, Dietmar A ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Density functional calculations; Epoxidations; Gas phase chemistry; Manganese; Mass spectrometry

Indexed keywords

LIGAND; MANGANESE DERIVATIVE; METAL COMPLEX; OXYGEN; SALEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; COMPLEX FORMATION; ELECTRON TRANSPORT; EPOXIDATION; MASS SPECTROMETRY; OXIDATION; OXYGEN TRANSPORT;

EID: 0035793305     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010202)7:3<591::AID-CHEM591>3.0.CO;2-I     Document Type: Article

References (83)

1. W. J. Mijs, C. R. H. I. De Jonge, Organic Syntheses by Oxidation with Metal Compounds, Plenum, New York, 1986.
2. C. C. Reddy, G. A. Hamilton, K. M. Madyashta, Biological Oxidation Systems, Academic Press, San Diego, 1990.
3. R. Sato, T. Omura, Cytochrome P-450, Kodansha, Tokyo, 1978.
4. R. E. White, M. J. Coon, Annu. Rev. Biochem. 1980, 49, 315-356.
5. T. G. Traylor, P. S. Traylor in Active Oxygen in Biochemistry (Eds.: J. S. Valentine, C. S. Foote, J. F. Liebman, A. Greenberg), Blackie Academic, London, 1995, pp. 84-187.
6. Cytochrome P-450, Structure, Mechanism and Biochemistry (Ed.: P. R. Ortiz de Montellano), Plenum, New York, 1995.
7. T. Mann in Oxidases and Related Systems (Eds.: T. E. King, H. S. Mason, M. Morrison), Liss, New York, 1988, pp. 29-49.
8. Y.-C. Fann, N. C. Gerber, P. A. Osmulski, L. P. Hager, S. G. Sligar, B. M. Hoffmann, J. Am. Chem. Soc. 1994, 116, 5989-5990.
9. a) K. McMillan, D. S. Bredt, D. J. Hirsch, S. H. Snyder, J. E. Clark, B. S. S. Masters, Proc. Natl. Acad. Sci. USA 1992, 89, 1141-1145;
10. b) K. A. White, M. A. Marletta, Biochemistry 1992, 31, 6627-6631;
11. c) M. A. Marletta, J. Biol. Chem. 1993, 268, 12 231-12 234.
12. J. T. Groves, W. J. Kruper, T. E. Nemo, R. S. Myers, J. Mol. Catal. 1980, 7, 169-177.
13. Metalloporphyrins in Catalytic Oxidations (Ed.: R. A. Sheldon), Dekker, New York, 1994.
14. Metalloporphyrin Catalyzed Oxidations (Eds.: F. Montanari, L. CaseHa), Kluwer, Dordrecht, 1994.
15. T. L. Siddall, N. Miyaura, J. C. Huffman, J. K. Kochi, J. Chem. Soc. Chem. Commun. 1983, 1185-1186.
16. E. G. Samsel, K. Srinivasan, J. K. Kochi, J. Am. Chem. Soc. 1985, 107, 7606-7617.
17. K. Srinivasan, J. K. Kochi, Inorg. Chem. 1985, 24, 4671-4679.
18. K. Srinivasan, P. Michaud, J. K. Kochi, J. Am. Chem. Soc. 1986, 108, 2309-2320.
19. K. Srinivasan, S. Perrier, J. K. Kochi, J. Mol. Catal. 1986, 36, 297-317.
20. W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-2803.
21. R. Irie, K. Noda, Y. Ito, N. Matsumoto, T. Katsuki, Tetrahedron Lett. 1990, 31, 7345-7348.
22. E. N. Jacobsen in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: G. W. Wilkinson, F. G. A. Stone, E. W. Abel, L. S. Hegedus), Pergamon, New York, 1995, Chapter 11.1.
23. C. T. Dalton, K. M. Ryan, V. M. Wall, C. Bousquet, D. G. Gilheany, Top. Catal. 1998, 5, 75-91.
24. J. T. Groves, W. J. Kruper, J. Am. Chem. Soc. 1979, 101, 7613-7615.
25. M. Yamashita, J. B. Fenn, J. Phys. Chem. 1984, 88, 4451-4459.
26. The basic electrospray source for mass spectrometry is described by: C. M. Whitehouse, R. N. Dreyer, M. Yamashita, J. B. Fenn, Anal. Chem. 1985, 57, 675-679.
27. A complete monograph on the technique is: Electrospray Ionization Mass Spectrometry (Ed.: R. D. Cole), Wiley, New York, 1997.
28. a) R. Colton, J. C. Traeger, Inorg. Chim. Acta 1992, 201, 153-155;
29. b) R. Colton, A. D'Agostino, J. C. Traeger, Mass Spectrom. Rev. 1995, 14, 79-106, and references cited therein.
30. a) V. Katta, S. K. Chowdhury, B. T. Chait, J. Am. Chem. Soc. 1990, 112, 5348-5349;
31. b) S. R. Wilson, Y. H. Wu, Organometallics 1993, 12, 1478-1480;
32. c) A. O. Aliprantis, J. W. Canary, J. Am. Chem. Soc. 1994, 116, 6985-6986;
33. d) L. A. P. Kane-Maguire, R. Kanitz, M. M. Sheil, J. Organomet. Chem. 1995, 486, 243-248;
34. e) C. Q. Jiao, B. S. Freiser, S. R. Carr, C. J. Cassidy, J. Am. Chem. Soc. Mass Spectrom. 1995, 6, 521-524;
35. f) K. S. Wang, X. L. Han, R. W. Gross, G. W. Gokel, J. Am. Chem. Soc. 1995, 117, 7680-7686;
36. g) L. Ripa, A. Hallberg, J. Org. Chem. 1996, 61, 7147-7155;
37. h) Z. M. Dzhabieva, V. P. Kozlovskii, Yu. M. Shul'ga, A. F. Dodonov, G. P. Belov, Russ. Chem. Bull. 1996, 45, 474-476;
38. i) J. M. Brown, K. K. Hii, Angew. Chem. 1996, 108, 679-682;
39. Angew. Chem. Int. Ed. Engl. 1996, 35, 657-659;
40. j) K. K. Hii, T. D. W. Claridge, J. M. Brown, Angew. Chem. 1997, 109, 1033-1036;
41. Angew. Chem. Int. Ed. Engl. 1997, 36, 984-987;
42. k) B. H. Lipshutz, K. L. Stevens, B. Lames, J. G. Pavlovich, J. P. Snyder, J. Am. Chem. Soc. 1996, 118, 6796-6797;
43. l) R. Saf, R. Schitter, C. Mirtl, F. Stelzer, K. Hummel, Macromolecules 1996, 29, 7651-7656;
44. m) K. A. Hirsch, S. R. Wilson, J. S. Moore, J. Am. Chem. Soc. 1997, 119, 10401-10412;
45. n) M. S. Stephan, A. J. J. M. Teunissen, G. K. M. Verzijl, J. G. de Vries, Angew. Chem. 1998, 110, 688-690;
46. Angew. Chem. Int. Ed. 1998, 37, 662-664.
47. a) C. Hinderling, D. A. Plattner, P. Chen, Angew. Chem. 1997, 109, 272-274;
48. Angew. Chem. Int. Ed. Engl. 1997, 36, 243-244;
49. b) C. Hinderling, D. Feichtinger, D. A. Plattner, P. Chen, J. Am. Chem. Soc. 1997, 119, 10 793-10 804.
50. D. Feichtinger, D. A. Plattner, P. Chen, J. Am. Chem. Soc. 1998, 120, 7125-7126.
51. D. Feichtinger, D. A. Plattner, Angew. Chem. 1997, 109, 1796-1798;
52. Angew. Chem. Int. Ed. Engl. 1997, 36, 1718-1719.
53. D. A. Plattner, D. Feichtinger, J. El-Bahroui, O. Wiest, Int. J. Mass Spectrom. 2000, 195/196, 351-362.
54. D. Feichtinger, D. A. Plattner, J. Chem. Soc. Perkin Trans. 2 2000, 1023-1028.
55. The use of p-cyanodimethylaniline N-oxide as an oxidant for manganese(III)-porphyrin complexes has been pioneered by Bruice et al. M. F. Powell, E. F. Pai, T. C. Bruice, J. Am. Chem. Soc. 1984, 106, 3277-3285.
56. a) K. M. Ervin, P. B. Armentrout, J. Chem. Phys. 1985, 83, 166-189;
57. b) S. K. Loh, D. A. Hales, L. Lian, P. B. Armentrout, J. Chem. Phys. 1989, 90, 5466-5485;
58. c) R. H. Schultz, P. B. Armentrout, Int. J. Mass Spectrom. Ion Processes 1991, 107, 29-48;
59. d) R. H. Schultz, K. C. Crellin, P. B. Armentrout, J. Am. Chem. Soc. 1991, 113, 8590-8601;
60. e) N. F. Dalleska, K. Honma, L. S. Sunderlin, P. B. Armentrout, J. Am. Chem. Soc. 1994, 116, 3519-3528;
61. f) M. T. Rodgers, K. M. Ervin, P. B. Armentrout, J. Chem. Phys. 1997, 106, 4499-4508.
62. A similar method that translates kinetic branching ratios into thermochemical data in cases when the difference in entropy change between two different fragmentation pathways can be neglected was introduced by Cooks. The assumptions inherent in the "Cooks' kinetic method" were essentially the same as those required for linear free energy relationships, that is, Hammett σρ correlations. The kinetic method has been widely used for the determination of proton affinities and gas-phase basicities of many organic compounds, and this has yielded values in excellent agreement with independent methods. a) R. G. Cooks, J. S. Patrick, T. Kotiaho, S. A. McLuckey, Mass Spectrom. Rev. 1994, 13, 287-339;
63. b) R. G. Cooks, P. S. H. Wong, Acc. Chem. Res. 1998, 31, 379-386, and references cited therein.
64. a) W. M. Coleman, R. R. Goehring, L. T. Taylor, J. G. Mason, R. K. Boggess, J. Am. Chem. Soc. 1979, 101, 2311-2315;
65. b) W. M. Coleman, R. K. Boggess, J. W. Hughes, L. T. Taylor, Inorg. Chem. 1981, 20, 700-706;
66. c) W. M. Coleman, R. K. Boggess, J. W. Hughes, L. T. Taylor, Inorg. Chem. 1981, 20, 1253-1258.
67. H. C. Brown, Y. Okamoto, J. Am. Chem. Soc. 1958, 80, 4979-4987.
68. The ground state of the manganese(III) complex is quintet. As for the ground state of the manganese(V) oxo complex, calculations on salen model systems point to triplet ground states: a) T. Strassner, K. N. Houk, Org. Lett. 1999, 1, 419-421;
69. b) C. Linde, B. Åkermark, P.-O. Norrby, M. Svensson, J. Am. Chem. Soc. 1999, 121, 5083-5084;
70. c) L. Cavallo, H. Jacobsen, Angew. Chem. 2000, 112, 602-604;
71. Angew. Chem. Int. Ed. 2000, 39, 589-592. Preliminary calculations in our group on the singlet states of oxomanganese(V)-salen show them very close in energy to the triplets. In view of the above cited model studies, we decided to use the triplet energies for the homodesmotic reaction.
72. E. N. Jacobsen, W. Zhang, M. L. Güler, J. Am. Chem. Soc. 1991, 113, 6703-6704.
73. M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Güler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954.
74. N. S. Finney, P. J. Pospisil, S. Chang, M. Palucki, R. G. Konsler, K. B. Hansen, E. N. Jacobsen, Angew. Chem. 1997, 109, 1798-1801;
75. Angew. Chem. Int. Ed. Engl. 1997, 36, 1720-1723.
76. D. Feichtinger, D. A. Plattner, unpublished results.
77. In our ESMS experiments, we have always used a combination of amine N-oxides and iodosobenzene in order to get higher yields of the μ-oxomanganese(IV) complexes and better reproducibility of the oxidized species than would be possible with N-oxides as the only oxygen source.
78. W. Zhang, E. N. Jacobsen, J. Org. Chem. 1991, 56, 2296-2298.
79. J. Cymerman Craig, K. K. Purushothaman, J. Org. Chem. 1970, 35, 1721-1722.
80. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision C.3, Gaussian, Pittsburgh PA, 1995.
81. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
82. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
83. c) P. J. Stevens, F. J. Devlin, C. F. Chablowski, M. J. Frisch, J. Phys. Chem. 1994, 95, 11 623-11 627.