Water as an Oxygen Source: Synthesis, Characterization, and Reactivity Studies of a Mononuclear Nonheme Manganese(IV) Oxo Complex†
Dr. Sarvesh C. Sawant
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorXiujuan Wu
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Jaeheung Cho
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Kyung-Bin Cho
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Sun Hee Kim
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Mi Sook Seo
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Yong-Min Lee
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Minoru Kubo
Picobiology Institute, Graduate School of Life Science, University of Hyogo (Japan)
Search for more papers by this authorProf. Dr. Takashi Ogura
Picobiology Institute, Graduate School of Life Science, University of Hyogo (Japan)
Search for more papers by this authorProf. Dr. Sason Shaik
Department of Organic Chemistry and The Lise Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem (Israel)
Search for more papers by this authorProf. Dr. Wonwoo Nam
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Sarvesh C. Sawant
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorXiujuan Wu
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Jaeheung Cho
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Kyung-Bin Cho
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Sun Hee Kim
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Mi Sook Seo
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Yong-Min Lee
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorDr. Minoru Kubo
Picobiology Institute, Graduate School of Life Science, University of Hyogo (Japan)
Search for more papers by this authorProf. Dr. Takashi Ogura
Picobiology Institute, Graduate School of Life Science, University of Hyogo (Japan)
Search for more papers by this authorProf. Dr. Sason Shaik
Department of Organic Chemistry and The Lise Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem (Israel)
Search for more papers by this authorProf. Dr. Wonwoo Nam
Department of Bioinspired Science, Department of Chemistry and Nano Science and Centre for Biomimetic Systems, Ewha Womans University, Seoul 120–750 (Korea), Fax: (+82) 2-3277-4441
Search for more papers by this authorThe research at EWU was supported by NRF/MEST of Korea through the CRI, WCU (R31-2008-000-10010-0), and GRL (2010-00353) Programs (to W.N.). The research at UH was supported by Grant-in-Aid for scientific research (C) (no. 21570171; to T.O.) by MEXT (Japan). S.S. thanks the Israel Science Foundation (Grant 16/06).
Graphical Abstract
The source of the problem: Experiments with isotopically labeled water can be used to unambiguously assign the source of oxygen in a nonheme manganese(IV) oxo complex. The complex, which was generated using water as an oxygen source and cerium(IV) as an oxidant (see picture), shows reactivities in the activation of CH bonds of alkyl-functionalized aromatic molecules and the oxidation of aromatic substrates (sub) and benzyl alcohol.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
anie_201000819_sm_miscellaneous_information.pdf600.3 KB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aJ. P. McEvoy, G. W. Brudvig, Chem. Rev. 2006, 106, 4455–4483;
- 1bT. J. Meyer, M. H. V. Huynh, H. H. Thorp, Angew. Chem. 2007, 119, 5378–5399; Angew. Chem. Int. Ed. 2007, 46, 5284–5304;
- 1cV. L. Pecoraro, W.-Y. Hsieh, Inorg. Chem. 2008, 47, 1765–1778;
- 1dJ. Barber, Chem. Soc. Rev. 2009, 38, 185–196;
- 1eW. Lubitz, E. J. Reijerse, J. Messinger, Energy Environ. Sci. 2008, 1, 15–31.
- 2
- 2aB. Meunier, A. Robert, G. Pratviel, J. Bernadou in The Porphyrin Handbook, Vol. 4 (Eds.: ), Academic Press, San Diego, 2000, pp. 119–187;
- 2bJ. T. Groves in Cytochrome P450: Structure, Mechanism, and Biochemistry, 3rd ed. ), Kluwer Academic/Plenum Publishers, New York, 2005, pp. 1–43.
10.1007/0-387-27447-2_1 Google Scholar
- 3
- 3aJ. T. Groves, J. Lee, S. S. Marla, J. Am. Chem. Soc. 1997, 119, 6269–6273;
- 3bN. Jin, J. T. Groves, J. Am. Chem. Soc. 1999, 121, 2923–2924;
- 3cN. Jin, J. L. Bourassa, S. C. Tizio, J. T. Groves, Angew. Chem. 2000, 112, 4007–4009;
Angew. Chem. Int. Ed. 2000, 39, 3849–3851;
10.1002/1521-3773(20001103)39:21<3849::AID-ANIE3849>3.0.CO;2-0 CAS PubMed Web of Science® Google Scholar
- 3dF. De Angelis, N. Jin, R. Car, J. T. Groves, Inorg. Chem. 2006, 45, 4268–4276;
- 3eN. Jin, M. Ibrahim, T. G. Spiro, J. T. Groves, J. Am. Chem. Soc. 2007, 129, 12416–12417.
- 4aW. Nam, I. Kim, M. H. Lim, H. J. Choi, J. S. Lee, H. G. Jang, Chem. Eur. J. 2002, 8, 2067–2071;
10.1002/1521-3765(20020503)8:9<2067::AID-CHEM2067>3.0.CO;2-V CAS PubMed Web of Science® Google Scholar
- 4bW. J. Song, M. S. Seo, S. D. George, T. Ohta, R. Song, M.-J. Kang, T. Tosha, T. Kitagawa, E. I. Solomon, W. Nam, J. Am. Chem. Soc. 2007, 129, 1268–1277;
- 4cJ. Y. Lee, Y.-M. Lee, H. Kotani, W. Nam, S. Fukuzumi, Chem. Commun. 2009, 704–706;
- 4dC. Arunkumar, Y.-M. Lee, J. Y. Lee, S. Fukuzumi, W. Nam, Chem. Eur. J. 2009, 15, 11482–11489;
- 4eS. Fukuzumi, N. Fujioka, H. Kotani, K. Ohkubo, Y.-M. Lee, W. Nam, J. Am. Chem. Soc. 2009, 131, 17127–17134.
- 5aR. Zhang, M. Newcomb, J. Am. Chem. Soc. 2003, 125, 12418–12419;
- 5bR. Zhang, J. H. Horner, M. Newcomb, J. Am. Chem. Soc. 2005, 127, 6573–6582.
- 6Y. Shimazaki, T. Nagano, H. Takesue, B.-H. Ye, F. Tani, Y. Naruta, Angew. Chem. 2004, 116, 100–102;
10.1002/ange.200352564 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 98–100.
- 7aR. L. Shook, A. S. Borovik, Inorg. Chem. 2010, 49, 3646–3660;
- 7bT. H. Parsell, M.-Y. Yang, A. S. Borovik, J. Am. Chem. Soc. 2009, 131, 2762–2763;
- 7cT. H. Parsell, R. K. Behan, M. T. Green, M. P. Hendrich, A. S. Borovik, J. Am. Chem. Soc. 2006, 128, 8728–8729.
- 8aG. Yin, J. M. McCormick, M. Buchalova, A. M. Danby, K. Rodgers, V. W. Day, K. Smith, C. M. Perkins, D. Kitko, J. D. Carter, W. M. Scheper, D. H. Busch, Inorg. Chem. 2006, 45, 8052–8061;
- 8bG. Yin, A. M. Danby, D. Kitko, J. D. Carter, W. M. Scheper, D. H. Busch, J. Am. Chem. Soc. 2007, 129, 1512–1513;
- 8cG. Yin, A. M. Danby, D. Kitko, J. D. Carter, W. M. Scheper, D. H. Busch, J. Am. Chem. Soc. 2008, 130, 16245–16253;
- 8dT. Kurahashi, A. Kikuchi, T. Tosha, Y. Shiro, T. Kitagawa, H. Fujii, Inorg. Chem. 2008, 47, 1674–1686;
- 8eT. Kurahashi, A. Kikuchi, Y. Shiro, M. Hada, H. Fujii, Inorg. Chem. 2010, 49, 6664–6672.
- 9
- 9aT. J. Collins, R. D. Powell, C. Slebodnick, E. S. Uffelman, J. Am. Chem. Soc. 1990, 112, 899–901;
- 9bF. M. MacDonnell, N. L. P. Fackler, C. Stern, T. V. O’Halloran, J. Am. Chem. Soc. 1994, 116, 7431–7432.
- 10
- 10aX. Sala, I. Romero, M. Rodríguez, L. Escriche, A. Llobet, Angew. Chem. 2009, 121, 2882–2893;
10.1002/ange.200802659 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 2842–2852;
- 10bS. Romain, L. Vigara, A. Llobet, Acc. Chem. Res. 2009, 42, 1944–1953;
- 10cF. Liu, J. J. Concepcion, J. W. Jurss, T. Cardolaccia, J. L. Templeton, T. J. Meyer, Inorg. Chem. 2008, 47, 1727–1752;
- 10dJ. K. Hurst, J. L. Cape, A. E. Clark, S. Das, C. Qin, Inorg. Chem. 2008, 47, 1753–1764.
- 11aY. Hirai, T. Kojima, Y. Mizutani, Y. Shiota, K. Yoshizawa, S. Fukuzumi, Angew. Chem. 2008, 120, 5856–5860;
10.1002/ange.200801170 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 5772–5776;
- 11bC.-M. Che, V. W.-W. Yam, T. C. W. Mak, J. Am. Chem. Soc. 1990, 112, 2284–2291.
- 12
- 12aF. Bozoglian, S. Romain, M. Z. Ertem, T. K. Todorova, C. Sens, J. Mola, M. Rodríguez, I. Romero, J. Benet-Buchholz, X. Fontrodona, C. J. Cramer, L. Gagliardi, A. Llobet, J. Am. Chem. Soc. 2009, 131, 15176–15187;
- 12bA. Sartorel, M. Carraro, G. Scorrano, R. De Zorzi, S. Geremia, N. D. McDaniel, S. Bernhard, M. Bonchio, J. Am. Chem. Soc. 2008, 130, 5006–5007;
- 12cY. V. Geletii, B. Botar, P. Kögerler, D. A. Hillesheim, D. G. Musaev, C. L. Hill, Angew. Chem. 2008, 120, 3960–3963;
10.1002/ange.200705652 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 3896–3899;
- 12dJ. A. Gilbert, D. S. Eggleston, W. R. Murphy, Jr., D. A. Geselowitz, S. W. Gersten, D. J. Hodgson, T. J. Meyer, J. Am. Chem. Soc. 1985, 107, 3855–3864.
- 13Y.-M. Lee, S. N. Dhuri, S. C. Sawant, J. Cho, M. Kubo, T. Ogura, S. Fukuzumi, W. Nam, Angew. Chem. 2009, 121, 1835–1838; Angew. Chem. Int. Ed. 2009, 48, 1803–1806.
- 14For the synthesis of a mononuclear nonheme MnIII oxo complex using water as an oxygen source, see:
- 14aR. Gupta, C. E. MacBeth, V. G. Young, Jr., A. S. Borovik, J. Am. Chem. Soc. 2002, 124, 1136–1137;
- 14bC. E. MacBeth, R. Gupta, K. R. Mitchell-Koch, V. G. Young, Jr., G. H. Lushington, W. H. Thompson, M. P. Hendrich, A. S. Borovik, J. Am. Chem. Soc. 2004, 126, 2556–2567;
- 14cA. S. Borovik, Acc. Chem. Res. 2005, 38, 54–61.
- 15
- 15aK. A. Campbell, M. R. Lashley, J. K. Wyatt, M. H. Nantz, R. D. Britt, J. Am. Chem. Soc. 2001, 123, 5710–5719;
- 15bD. P. Kessissoglou, X. Li, W. M. Butler, V. L. Pecoraro, Inorg. Chem. 1987, 26, 2487–2492.
- 16Spectral simulations were carried out using EasySpin 3.0: S. Stoll, A. Schweiger, J. Magn. Reson. 2006, 178, 42–55.
- 17
- 17aR. S. Czernuszewicz, Y. O. Su, M. K. Stern, K. A. Macor, D. Kim, J. T. Groves, T. G. Spiro, J. Am. Chem. Soc. 1988, 110, 4158–4165;
- 17bR. Makino, T. Uno; Y. Nishimura, T. Iizuka, M. Tsuboi, Y. Ishimura, J. Biol. Chem. 1986, 261, 8376–8382.
- 18
- 18aA. D. Becke, Phys. Rev. A 1988, 38, 3098–3100;
- 18bA. D. Becke, J. Chem. Phys. 1993, 98, 1372–1377;
- 18cA. D. Becke, J. Chem. Phys. 1993, 98, 5648–5652;
- 18dC. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785–789;
- 18eP. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299–310.
- 19K. Ayougou, E. Bill, J. M. Charnock, C. D. Garner, D. Mandon, A. X. Trautwein, R. Weiss, H. Winkler, Angew. Chem. 1995, 107, 370–373;
10.1002/ange.19951070324 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 343–346.
- 20
- 20aW. W. Y. Lam, W.-L. Man, T.-C. Lau, Coord. Chem. Rev. 2007, 251, 2238–2252;
- 20bJ. M. Mayer, Biomimetic Oxidations Catalyzed by Transition Metal Complexes (Ed.: ), Imperial College Press, London, 2000, pp. 1–43;
10.1142/9781848160699_0001 Google Scholar
- 20cJ. P. Roth, J. M. Mayer, Inorg. Chem. 1999, 38, 2760–2761.
- 21C. V. Sastri, J. Lee, K. Oh, Y. J. Lee, J. Lee, T. A. Jackson, K. Ray, H. Hirao, W. Shin, J. A. Halfen, J. Kim, L. Que, Jr., S. Shaik, W. Nam, Proc. Natl. Acad. Sci. USA 2007, 104, 19181–19186.
- 22
- 22aS. P. de Visser, K. Oh, A.-R Han, W. Nam, Inorg. Chem. 2007, 46, 4632–4641;
- 22bM.-J. Kang, W. J. Song, A.-R. Han, Y. S. Choi, H. G. Jang, W. Nam, J. Org. Chem. 2007, 72, 6301–6304.
- 23S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2003, 125, 7413–7424.
- 24K. Nehru, S. J. Kim, I. Y. Kim, M. S. Seo, Y. Kim, S.-J. Kim, J. Kim, W. Nam, Chem. Commun. 2007, 4623–4625.
- 25
- 25aA. Murphy, G. Dubois, T. D. P. Stack, J. Am. Chem. Soc. 2003, 125, 5250–5251;
- 25bA. Murphy, A. Pace, T. D. P. Stack, Org. Lett. 2004, 6, 3119–3122.
- 26N. Y. Oh, Y. Suh, M. J. Park, M. S. Seo, J. Kim, W. Nam, Angew. Chem. 2005, 117, 4307–4311;
10.1002/ange.200500623 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 4235–4239.