Catalytically Enhanced NMR of Heterogeneously Catalyzed Hydrogenations
Vladimir V. Zhivonitko
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorKirill V. Kovtunov
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorIvan V. Skovpin
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorDanila A. Barskiy
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorOleg G. Salnikov
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorIgor V. Koptyug
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorVladimir V. Zhivonitko
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorKirill V. Kovtunov
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorIvan V. Skovpin
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorDanila A. Barskiy
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorOleg G. Salnikov
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorIgor V. Koptyug
International Tomography Center, SB RAS, 3A Institutskaya Street, Novosibirsk, 630090, Russia
Novosibirsk State University, Department of Natural Sciences, 2 Pirogova Street, Novosibirsk, 630090, Russia
Search for more papers by this authorValentine P. Ananikov
Russian Academy of Sciences, Zelinsky, Institute of Organic Chemistry, 47 Leninski Prospect, 119991 Moscow, Russia
Search for more papers by this authorSummary
When used in catalytic hydrogenations, parahydrogen can enhance NMR signals of reaction products and intermediates by several orders of magnitude owing to the phenomenon of parahydrogen-induced polarization (PHIP). This possibility has been explored previously in the context of activation of molecular hydrogen by transition metal complexes and clusters in solution. After a brief introduction to parahydrogen and PHIP basics, the applications of PHIP as a mechanistic tool in homogeneous catalysis are briefly reviewed to demonstrate the possibilities and the information that PHIP-based NMR spectroscopy studies of such processes can provide. Then, the emerging applications of PHIP-enhanced NMR in heterogeneous catalysis are presented, both for metal complexes immobilized on solid supports and for supported metal catalysts, and the implications of these results for the mechanisms of heterogeneous hydrogenation processes are discussed.
References
- Roe, D.C., Kating, P.M., Krusic, P.J., and Smart, B.E. (1998) Top. Catal., 5, 133–147.
- Elsevier, C.J. (1994) J. Mol. Catal., 92, 285–297.
-
J. Bargon and L. Kuhn (eds) (2007) In situ NMR Methods in Catalysis, Topics in Current Chemistry, Springer-Verlag Berlin Heidelberg, vol. 276.
10.1007/978-3-540-71427-9 Google Scholar
- Hunger, M. and Wang, W. (2006) Adv. Catal., 50, 147–225.
- Ivanova, I.I. and Kolyagin, Y.G. (2010) Chem. Soc. Rev., 39, 5018–5050.
- Blasco, T. (2010) Chem. Soc. Rev., 39, 4685–4702.
- Belyakov, P.A., Kadentsev, V.I., Chizhov, A.O., Kolotyrkina, N.G., Shashkov, A.S., and Ananikov, V.P. (2010) Mendeleev Commun., 20, 125–131.
- Lysova, A.A. and Koptyug, I.V. (2010) Chem. Soc. Rev., 39, 4585–4601.
-
L. Kuhn (ed.) (2013) Hyperpolarization Methods in NMR Spectroscopy, Topics in Current Chemistry, Springer-Verlag Berlin Heidelberg, vol. 338.
10.1007/978-3-642-39728-8 Google Scholar
- Mansson, S., Johansson, E., Magnusson, P., Chai, C.-M., Hansson, G., Petersson, J.S., Stahlberg, F., and Golman, K. (2006) Eur. Radiol., 16, 57–67.
- Bowers, C.R. and Weitekamp, D.P. (1987) J. Am. Chem. Soc., 109, 5541–5542.
- Duckett, S.B. and Wood, N.J. (2008) Coord. Chem. Rev., 252, 2278–2291.
- Natterer, J. and Bargon, J. (1997) Prog. NMR Spectrosc., 31, 293–315.
- Canet, D., Aroulanda, C., Mutzenhardt, P., Aime, S., Gobetto, R., and Reineri, F. (2006) Concepts Magn. Reson., 28A, 321–330.
- Kovtunov, K.V., Zhivonitko, V.V., Skovpin, I.V., Barskiy, D.A., and Koptyug, I.V. (2013) Top. Curr. Chem., 338, 123–180.
- Landau, L.D. and Lifschitz, E.M. (1977) Quantum Mechanics: Non-Relativistic Theory, 3rd edn, Pergamon Press, Oxford.
- Bunker, P.R. and Jensen, P. (2006) Molecular Symmetry and Spectroscopy, 2nd edn, NRC Research Press, Ottawa.
- Hovener, J.-B., Bar, S., Leupold, J., Jenne, K., Leibfritz, D., Hennig, J., Duckett, S.B., and von Elverfeldt, D. (2013) NMR Biomed., 26, 124–131.
- Farkas, A. and Farkas, L. (1938) J. Am. Chem. Soc., 60, 22–28.
- Twigg, G.H. (1950) Discuss. Faraday Soc., 8, 152–159.
- Farkas, A. and Farkas, L. (1939) J. Am. Chem. Soc., 61, 3396–3401.
- Bowers, C.R. and Weitekamp, D.P. (1986) Phys. Rev. Lett., 57, 2645–2648.
- Pravica, M.G. and Weitekamp, D.P. (1988) Chem. Phys. Lett., 145, 255–258.
- Kuhn, L.T. and Bargon, J. (2007) Top. Curr. Chem., 276, 25–68.
- Duckett, S.B. and Mewis, R.E. (2012) Acc. Chem. Res., 45, 1247–1257.
- Green, R.A., Adams, R.W., Duckett, S.B., Mewis, R.E., Williamson, D.C., and Green, G.G.R. (2012) Prog. NMR Spectrosc., 67, 1–48.
- Blazina, D., Duckett, S.B., Dunne, J.P., and Godard, C. (2004) Dalton Trans., 2601–2609.
- Duckett, S.B. and Blazina, D. (2003) Eur. J. Inorg. Chem., 16, 2901–2912.
- Duckett, S.B. and Sleigh, C.J. (1999) Prog. NMR Spectrosc., 34, 71–92.
- Eisenberg, R., Eisenschmid, T.C., Chinn, M.S., and Kirss, R.U. (1992) Adv. Chem. Ser., 230, 47–74.
- Eisenberg, R. (1991) Acc. Chem. Res., 24, 110–116.
- Kirss, R.U., Eisenschmid, T.C., and Eisenberg, R. (1988) J. Am. Chem. Soc., 110, 8564–8566.
- Klages, S., Permin, A.B., Petrosyan, V.S., and Bargon, J. (1997) J. Organomet. Chem., 545, 201–205.
- Schleyer, D., Niessen, H.G., and Bargon, J. (2001) New J. Chem., 25, 423–426.
- Viale, A., Santelia, D., Napolitano, R., Gobetto, R., Dastru, W., and Aime, S. (2008) Eur. J. Inorg. Chem., 4348–4351.
- Niessen, H.G., Schleyer, D., Wiemann, S., Bargon, J., Steiner, S., and Driessen-Holscher, B. (2000) Magn. Reson. Chem., 38, 747–750.
- Harthun, A., Bargon, J., and Selke, R. (1994) Tetrahedron Lett., 35, 7755.
- Harthun, A., Barkemeyer, J., Selke, R., and Bargon, J. (1995) Tetrahedron Lett., 36, 7423–7426.
- Harthun, A., Giernoth, R., Elsevier, C.J., and Bargon, J. (1996) Chem. Commun., 2483–2484.
- Harthun, A., Selke, R., and Bargon, J. (1996) Angew. Chem., Int. Ed. Engl., 35, 2505–2507.
-
Giernoth, R., Hubler, P., and Bargon, J. (1998) Angew. Chem., Int. Ed. Engl., 37, 2473–2475.
10.1002/(SICI)1521-3773(19981002)37:18<2473::AID-ANIE2473>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- Bargon, J. (2007) in The Handbook of Homogeneous Hydrogenation (eds J.G. de Vries and C.J. Elsevier), Wiley-VCH Verlag GmbH, Weinheim, pp. 313–358.
- Hubler, P., Giernoth, R., Kummerle, G., and Bargon, J. (1999) J. Am. Chem. Soc., 121, 5311.
-
Hubler, P. and Bargon, J. (2000) Angew. Chem. Int. Ed., 39, 3701–3703.
10.1002/1521-3773(20001016)39:20<3701::AID-ANIE3701>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- Kirss, R.U. and Eisenberg, R. (1989) J. Organomet. Chem., 359, C22–C26.
- Permin, A.B. and Eisenberg, R. (2002) J. Am. Chem. Soc., 124, 12406–12407.
- Godard, C., Duckett, S.B., Henry, C., Polas, S., Toose, R., and Whitwood, A.C. (2004) Chem. Commun., 1826–1827.
- Godard, C., Duckett, S.B., Polas, S., Tooze, R., and Whitwood, A.C. (2005) J. Am. Chem. Soc., 127, 4994–4995.
- Fox, D.J., Duckett, S.B., Flaschenriem, C., Brennessel, W.W., Schneider, J., Gunay, A., and Eisenberg, R. (2006) Inorg. Chem., 45, 7197–7209.
- Godard, C., Duckett, S.B., Polas, S., Tooze, R., and Whitwood, A.C. (2009) Dalton Trans., 2496–2509.
- Eichhorn, A., Koch, A., and Bargon, J. (2001) J. Mol. Catal. A Chem., 174, 293–295.
- Duckett, S.B., Newell, C.L., and Eisenberg, R. (1994) J. Am. Chem. Soc., 116, 10548–10556.
- Duckett, S.B., Newell, C.L., and Eisenberg, R. (1997) J. Am. Chem. Soc., 119, 2068.
- Colebrooke, S.A., Duckett, S.B., Lohman, J.A.B., and Eisenberg, R. (2004) Chem. Eur. J., 10, 2459–2474.
- Giernoth, R. (2005) in Mechanisms in Homogeneous Catalysis. A Spectroscopic Approach (ed. B. Heaton), Wiley-VCH Verlag GmbH, Weinheim, pp. 359–378.
- Lopez-Serrano, J., Duckett, S.B., Aiken, S., Lenro, K.Q.A., Drent, E., Dunne, J.P., Konya, D., and Whitwood, N.C. (2007) J. Am. Chem. Soc., 129, 6513–6527.
- Lopez-Serrano, J., Duckett, S.B., and Lledos, A. (2006) J. Am. Chem. Soc., 128, 9596–9597.
- Colebrooke, S.A., Duckett, S.B., and Lohman, J.A.B. (2000) Chem. Commun., 685–686.
- Koch, A. and Bargon, J. (2001) Inorg. Chem., 40, 533–539.
- Duckett, S.B., Mawby, R.J., and Partridge, M.G. (1996) Chem. Commun., 383–384.
- Barkemeyer, J., Haake, M., and Bargon, J. (1995) J. Am. Chem. Soc., 117, 2927–2928.
- Aime, S., Gobetto, R., and Canet, D. (1998) J. Am. Chem. Soc., 120, 6770–6773.
- Messerle, B.A., Sleigh, C.J., Partridge, M.G., and Duckett, S.B. (1999) J. Chem. Soc., Dalton Trans., 1429–1435.
- Hasnip, S.K., Duckett, S.B., Sleigh, C.J., Taylor, D.R., Barlow, G.K., and Taylor, M.J. (1999) Chem. Commun., 1717–1718.
- Hasnip, S.K., Colebrooke, S.A., Sleigh, C.J., Duckett, S.B., Taylor, D.R., Barlow, G.K., and Taylor, M.J. (2002) J. Chem. Soc., Dalton Trans., 743–751.
- Atesin, A.C., Duckett, S.B., Flaschenriem, C., Brennessel, W.W., and Eisenberg, R. (2007) Inorg. Chem., 46, 1196–1204.
- Malacea, R., Daran, J.-C., Duckett, S.B., Dunne, J.P., Godard, C., Manoury, E., Poli, R., and Whitwood, A.C. (2006) Dalton Trans., 3350–3359.
- Bregel, D.C., Oldham, S.M., and Eisenberg, R. (2002) J. Am. Chem. Soc., 124, 13827–13832.
- Bregel, D.C., Oldham, S.M., Lachicotte, R.J., and Eisenberg, R. (2002) Inorg. Chem., 41, 4371–4377.
- Aime, S., Dastru, W., Gobetto, R., Reineri, F., Russo, A., and Viale, A. (2001) Organometallics, 20, 2924–2927.
- Bergman, B., Rosenberg, E., Gobetto, R., Aime, S., Milone, L., and Reineri, F. (2002) Organometallics, 21, 1508–1511.
- Eisenschmid, T.C., Kirss, R.U., Deutsch, P.P., Hommeltoft, S.I., Eisenberg, R., Bargon, J., Lawler, R.G., and Balch, A.L. (1987) J. Am. Chem. Soc., 109, 8089–8091.
- Aime, S., Dastru, W., Gobetto, R., Russo, A., Viale, A., and Canet, D. (1999) J. Phys. Chem. A, 103, 9702–9705.
-
Blazina, D., Duckett, S.B., Lohman, J.A.B., and Dyson, P.J. (2001) Angew. Chem. Int. Ed., 40, 3874–3877.
10.1002/1521-3773(20011015)40:20<3874::AID-ANIE3874>3.0.CO;2-9 CAS PubMed Web of Science® Google Scholar
- Blazina, D., Duckett, S.B., Dyson, P.J., Johnson, B.F.G., Lohman, J.A.B., and Sleigh, C.J. (2001) J. Am. Chem. Soc., 123, 9760–9768.
- Adams, R.W., Aguilar, J.A., Atkinson, K.D., Cowley, M.J., Elliott, P.I.P., Duckett, S.B., Green, G.G.R., Khazal, I.G., Lopez-Serrano, J., and Williamson, D.C. (2009) Science, 323, 1708–1711.
- Atkinson, K.D., Cowley, M.J., Elliott, P.I.P., Duckett, S.B., Green, G.G.R., Lopez-Serrano, J., and Whitwood, A.C. (2009) J. Am. Chem. Soc., 131, 13362–13368.
- Atkinson, K.D., Cowley, M.J., Duckett, S.B., Elliott, P.I.P., Green, G.G.R., Lpez-Serrano, J., Khazal, I.G., and Whitwood, A.C. (2009) Inorg. Chem., 48, 663–670.
- Cowley, M.J., Adams, R.W., Atkinson, K.D., Cockett, M.C.R., Duckett, S.B., Green, G.G.R., Lohman, J.A.B., Kerssebaum, R., Kilgour, D., and Mewis, R.E. (2011) J. Am. Chem. Soc., 133, 6134–6137.
- Blazina, D., Dunne, J.P., Aiken, S., Duckett, S.B., Elkington, C., McGrady, J.E., Poli, R., Walton, S.J., Anwar, M.S., Jones, J.A., and Carteret, N.A. (2006) Dalton Trans., 2072–2080.
- Dunne, J.P., Blazina, D., Aiken, S., Carteret, H.A., Duckett, S.B., Jones, J.A., Poli, R., and Whitwood, A.C. (2004) Dalton Trans., 3616–3628.
- Hasnip, S., Duckett, S.B., Taylor, D.R., and Taylor, M.J. (1998) Chem. Commun., 923–924.
- Blazina, D., Duckett, S.B., Halstead, T.K., Kozak, C.M., Taylor, R.J.K., Anwar, M.S., Jones, J.A., and Carteret, H.A. (2005) Magn. Reson. Chem., 43, 200–208.
- Barbaro, P. and Bianchini, C. (2002) Top. Catal., 19, 17–32.
-
D.J. Cole-Hamilton and R.P. Tooze (eds) (2006) Catalyst Separation, Recovery and Recycling: Chemistry and Process Design, Catalysis by Metal Complexes, vol. 30, Springer, Dordrecht.
10.1007/1-4020-4087-3 Google Scholar
- End, N. and Schoning, K.-U. (2004) Top. Curr. Chem., 242, 241–271.
- Merckle, C. and Blumel, J. (2005) Top. Catal., 34, 5–15.
- Wegener, S.L., Marks, T.J., and Stair, P.C. (2012) Acc. Chem. Res., 45, 206–214.
- Koptyug, I.V., Kovtunov, K.V., Burt, S.R., Anwar, M.S., Hilty, C., Han, S., Pines, A., and Sagdeev, R.Z. (2007) J. Am. Chem. Soc., 129, 5580–5586.
- Kovtunov, K.V. and Koptyug, I.V. (2008) in Magnetic Resonance Microscopy: Spatially Resolved NMR Techniques and Applications (eds S. Codd and J.D. Seymour), Wiley-VCH Verlag GmbH, Weinheim, pp. 101–115.
- Gutmann, T., Ratajczyk, T., Xu, Y., Breitzke, H., Grunberg, A., Dillenberger, S., Bommerich, U., Trantzschel, T., Bernarding, J., and Buntkowsky, G. (2010) Solid State Nucl. Magn. Reson., 38, 90–96.
- Abdulhussain, S., Breitzke, H., Ratajczyk, T., Grunberg, A., Srour, M., Arnaut, D., Weidler, H., Kunz, U., Kleebe, H.J., Bommerich, U., Bernarding, J., Gutmann, T., and Buntkowsky, G. (2014) Chem. Eur. J., 20, 1159–1166.
- Skovpin, I.V., Zhivonitko, V.V., and Koptyug, I.V. (2011) Appl. Magn. Reson., 41, 393–410.
- Osborn, J.A., Jardine, F.H., Young, J.F., and Wilkinson, G. (1966) J. Chem. Soc. A, 88, 1711–1732.
- Bouchard, L.-S., Kovtunov, K.V., Burt, S.R., Anwar, M.S., Koptyug, I.V., Sagdeev, R.Z., and Pines, A. (2007) Angew. Chem. Int. Ed., 46, 4064–4068.
- Halpern, J. (1982) Science, 217, 401–407.
- Gutmann, T., Sellin, M., Breitzke, H., Stark, A., and Buntkowsky, G. (2009) Phys. Chem. Chem. Phys., 11, 9170–9175.
- Mehnert, C.P., Mozeleski, E.J., and Cook, R.A. (2002) Chem. Commun., 3010–3011.
- Virtanen, P., Salmi, T., and Mikkola, J.-P. (2009) Ind. Eng. Chem. Res., 48, 10335–10342.
- Gong, Q., Klankermayer, J., and Blumich, B. (2011) Chem. Eur. J., 17, 13795–13799.
- Kovtunov, K.V., Zhivonitko, V.V., Kiwi-Minsker, L., and Koptyug, I.V. (2010) Chem. Commun., 46, 5764–5766.
- Kovtunov, K.V., Zhivonitko, V.V., Corma, A., and Koptyug, I.V. (2010) J. Phys. Chem. Lett., 1, 1705–1708.
- Zhang, X., Llabres i Xamena, F.X., and Corma, A. (2009) J. Catal., 265, 155–160.
- Cremer, P.S., Su, X., Shen, Y.R., and Somorjai, G.A. (1996) J. Phys. Chem., 100, 16302–16309.
- Kovtunov, K.V., Beck, I.E., Bukhtiyarov, V.I., and Koptyug, I.V. (2008) Angew. Chem. Int. Ed., 47, 1492–1495.
- Teschner, D., Vass, E., Havecker, M., Zafeiratos, S., Schnorch, P., Sauer, H., Knop-Gericke, A., Schlogl, R., Chamam, M., Wootsch, A., Canning, A.S., Gamman, J.J., Jackson, S.D., McGregor, J., and Gladden, L.F. (2006) J. Catal., 242, 26–37.
- Somorjai, G.A. and Zaera, F. (1982) J. Phys. Chem., 86, 3070–3078.
- Bond, G.C. (1997) Appl. Catal., A, 149, 3–25.
- Wasylenko, W. and Frei, H. (2005) J. Phys. Chem. B, 109, 16873–16878.
- Cremer, P.S., Su, X., Shen, Y.R., and Somorjai, G.A. (1996) J. Am. Chem. Soc., 118, 2942–2949.
- Sharma, R. and Bouchard, L.S. (2012) Sci. Rep., 2, 277.
- Zhivonitko, V.V., Kovtunov, K.V., Beck, I.E., Ayupov, A.B., Bukhtiyarov, V.I., and Koptyug, I.V. (2011) J. Phys. Chem. C, 115, 13386–13391.
- Farin, D. and Avnir, D. (1988) J. Am. Chem. Soc., 110, 2039–2045.
- McLeod, A.S. (2004) Chem. Eng. Res. Des., 82, 945–951.
- Borodzinski, A. (2001) Catal. Lett., 71, 169–175.
- Rioux, R.M., Hsu, B.B., Grass, M.E., Song, H., and Somorjai, G.A. (2008) Catal. Lett., 126, 10–19.
- Norskov, J.K., Bligaard, T., Hvolbaek, B., Abild-Pedersen, F., and Christensen, C.H. (2008) Chem. Soc. Rev., 37, 2163–2171.
- Salnikov, O.G., Kovtunov, K.V., Barskiy, D.A., Bukhtiyarov, V.I., Kaptein, R., and Koptyug, I.V. (2013) Appl. Magn. Reson., 44, 279–288.
- Kovtunov, K.V., Beck, I.E., Zhivonitko, V.V., Barskiy, D.A., Bukhtiyarov, V.I., and Koptyug, I.V. (2012) Phys. Chem. Chem. Phys., 14, 11008–11014.
- Teschner, D., Borsodi, J., Wootsch, A., Revay, Z., Havecker, M., Knop-Gericke, A., Jackson, S.D., and Schlogl, R. (2008) Science, 320, 86–89.
- Teschner, D., Revay, Z., Borsodi, J., Havecker, M., Knop-Gericke, A., Schlogl, R., Milroy, D., Jackson, S.D., Torres, D., and Sautet, P. (2008) Angew. Chem. Int. Ed., 47, 9274–9278.
- Ludwig, W., Savara, A., Schauermann, S., and Freund, H.-J. (2010) ChemPhysChem, 11, 2319–2322.
- Dupont, J., Fonseca, G.S., Umpierre, A.P., Fichtner, P.F.P., and Teixeira, S.R. (2002) J. Am. Chem. Soc., 124, 4228–4229.
- Ruta, M., Laurenczy, G., Dyson, P.J., and Kiwi-Minsker, L. (2008) J. Phys. Chem. C, 112, 17814–17819.
- Barskiy, D.A., Kovtunov, K.V., Primo, A., Corma, A., Kaptein, R., and Koptyug, I.V. (2012) ChemCatChem, 4, 2031–2035.
- Koptyug, I.V., Zhivonitko, V.V., and Kovtunov, K.V. (2010) ChemPhysChem, 11, 3086–3088.
- Balu, A.M., Duckett, S.B., and Luque, R. (2009) Dalton Trans., 5074–5076.
- Lopez-Serrano, J., Lledos, A., and Duckett, S.B. (2008) Organometallics, 27, 43–52.
- Schott, D., Callaghan, P., Dunne, J., Duckett, S.B., Godard, C., Goicoechea, J.M., Harvey, J.N., Lowe, J.P., Mawby, R.J., Mller, G., Perutz, R.N., Poli, R., and Whittlesey, M.K. (2004) Dalton Trans., 3218–3224.
- Kozinets, E.M., Fekete, M., Filippov, O.A., Belkova, N.V., Shubina, E.S., Poli, R., Duckett, S.B., and Manoury, E. (2013) Dalton Trans., 42, 11720–11730.
- Al-Ibadi, M.A.M., Duckett, S.B., and McGrady, J.E. (2012) Dalton Trans., 41, 4618–4625.
- Veber, S.L., Bagryanskaya, E.G., and Chapovsky, P.L. (2006) J. Exp. Theor. Phys., 102, 76–83.
- Cacciani, P., Cosleou, J., and Khelkhal, M. (2012) Phys. Rev. A, 85, 012521.
- Manca Tanner, C., Quack, M., and Schmidiger, D. (2013) J. Phys. Chem. A, 117, 10105–10118.
- Zhivonitko, V.V., Kovtunov, K.V., Chapovsky, P.L., and Koptyug, I.V. (2013) Angew. Chem. Int. Ed., 52, 13251–13255.
- Ustynyuk, Y.A., Gavrikov, A.V., and Sergeyev, N.M. (2006) Phys. Chem. Chem. Phys., 8, 5181–5184.
- Ustynyuk, U.A. and Gloriozov, I.P. (2009) Russ. Chem. Bull., 58, 1841–1846.
- Norskov, J.K., Abild-Pedersen, F., Studt, F., and Bligaard, T. (2011) Proc. Natl. Acad. Sci. U.S.A., 108, 937–943.
- Abild-Pedersen, F., Greeley, J., Studt, F., Rossmeisl, J., Munter, T.R., Moses, P.G., Skulason, E., Bligaard, T., and Norskov, J.K. (2007) Phys. Rev. Lett., 99, 016105.
- Sheth, P.A., Neurock, M., and Smith, C.M. (2005) J. Phys. Chem. B, 109, 12449–12466.
- Studt, F., Abild-Pedersen, F., Bligaard, T., Sorensen, R.Z., Christensen, C.H., and Norskov, J.K. (2008) Science, 320, 1320–1322.
- Krajci, M. and Hafner, J. (2012) J. Catal., 295, 70–80.
- Krajci, M. and Hafner, J. (2012) J. Phys. Chem. C, 116, 6307–6319.
- Loffreda, D., Delbecq, F., Vigne, F., and Sautet, P. (2006) J. Am. Chem. Soc., 128, 1316.
- Loffreda, D., Michel, C., Delbecq, F., and Sautet, P. (2013) J. Catal., 308, 374–385.
- Burgi, T. and Baiker, A. (2004) Acc. Chem. Res., 37, 909–917.
- Busygin, I., Taskinen, A., Nieminen, V., Toukoniitty, E., Stillger, T., Leino, R., and Murzin, D.Y. (2009) J. Am. Chem. Soc., 131, 4449–4462.
- Lopez, N., Łodziana, Z., Illas, F., and Salmeron, M.B. (2004) Phys. Rev. Lett., 93, 146103.
- Hafner, J. (2008) Monatsh. Chem., 139, 373–387.
- Lewis, E.A., Le, D., Murphy, C.J., Jewell, A.D., Mattera, M.F.G., Liriano, M.L., Rahman, T.S., and Sykes, E.C.H. (2012) J. Phys. Chem. C, 116, 25868–25873.
- Sharma, V., Crozier, P.A., Sharma, R., and Adams, J.B. (2012) Catal. Today, 180, 2–7.
- Lykhach, Y., Staudt, T., Vorokhta, M., Skala, T., Johanek, V., Prince, K.C., Matolin, V., and Libuda, J. (2012) J. Catal., 285, 6–9.
- Prins, R. (2012) Chem. Rev., 112, 2714–2738.
- Prins, R., Palfi, V.K., and Reiher, M. (2012) J. Phys. Chem. C, 116, 14274–14283.
- Reuter, K., Frenkel, D., and Scheffler, M. (2004) Phys. Rev. Lett., 93, 116105.
- Lee, E.Y.M., Ward, D.J., Alexandrowicz, G., Hedgeland, H., Allison, W., Ellis, J., and Pollak, E. (2010) Phys. Rev. Lett., 105, 136101.
- McIntosh, E.M., Wikfeldt, K.T., Ellis, J., Michaelides, A., and Allison, W. (2013) J. Phys. Chem. Lett., 4, 1565.
- Hansen, E.W. and Neurock, M. (2000) J. Catal., 196, 241–252.
- Kovtunov, K.V., Barskiy, D.A., Salnikov, O.G., Khudorozhkov, A.K., Bukhtiyarov, V.I., Prosvirin, I.P., and Koptyug, I.V. (2014) Chem. Commun., 50, 875–878.
- Twigg, G.H. and Rideal, E.K. (1939) Proc. R. Soc. London, Ser. A, 171, 55–69.
- Horiuti, I. and Polanyi, M. (1934) Trans. Faraday Soc., 30, 1164–1172.