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Volumn 44, Issue 1, 2011, Pages 36-46

Understanding hydrogen atom transfer: From bond strengths to marcus theory

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION COMPOUND; HYDROGEN; PROTON; RUTHENIUM;

EID: 78751499421     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar100093z     Document Type: Article
Times cited : (670)

References (47)
  • 3
    • 3042780720 scopus 로고    scopus 로고
    • Proton-Coupled Electron Transfer: A Reaction Chemist's View
    • Mayer, J. M. Proton-Coupled Electron Transfer: A Reaction Chemist's View Annu. Rev. Phys. Chem. 2004, 55, 363-390
    • (2004) Annu. Rev. Phys. Chem. , vol.55 , pp. 363-390
    • Mayer, J.M.1
  • 4
    • 36849008128 scopus 로고    scopus 로고
    • Proton-Coupled Electron Transfer
    • Huynh, M. H. V.; Meyer, T. J. Proton-Coupled Electron Transfer Chem. Rev. 2007, 107, 5004-5064
    • (2007) Chem. Rev. , vol.107 , pp. 5004-5064
    • Huynh, M.H.V.1    Meyer, T.J.2
  • 5
    • 0042932741 scopus 로고    scopus 로고
    • 2+ Occurs by Hydrogen Atom Abstraction
    • 2+ Occurs by Hydrogen Atom Abstraction J. Am. Chem. Soc. 2003, 125, 10351-10361
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 10351-10361
    • Bryant, J.R.1    Mayer, J.M.2
  • 7
    • 33846326411 scopus 로고    scopus 로고
    • Hydrogen Transfer Reactivity of a Ferric Bi-imidazoline Complex That Models the Activity of Lipoxygenase Enzymes
    • Roth, J. P.; Mayer, J. M. Hydrogen Transfer Reactivity of a Ferric Bi-imidazoline Complex That Models the Activity of Lipoxygenase Enzymes Inorg. Chem. 1999, 38, 2760-2761
    • (1999) Inorg. Chem. , vol.38 , pp. 2760-2761
    • Roth, J.P.1    Mayer, J.M.2
  • 8
    • 67749118152 scopus 로고    scopus 로고
    • Slow Hydrogen Atom Transfer Reactions of Oxo- and Hydroxo-Vanadium Compounds: The Importance of Intrinsic Barriers
    • Waidmann, C. R.; Zhou, X.; Tsai, E. A.; Kaminsky, W.; Hrovat, D. A.; Borden, W. T.; Mayer, J. M. Slow Hydrogen Atom Transfer Reactions of Oxo- and Hydroxo-Vanadium Compounds: The Importance of Intrinsic Barriers J. Am. Chem. Soc. 2009, 131, 4729-4743
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 4729-4743
    • Waidmann, C.R.1    Zhou, X.2    Tsai, E.A.3    Kaminsky, W.4    Hrovat, D.A.5    Borden, W.T.6    Mayer, J.M.7
  • 9
    • 67651224886 scopus 로고    scopus 로고
    • Concerted Proton-Electron Transfer in a Ruthenium Terpyridyl-Benzoate System with a Large Separation between the Redox and Basic Sites
    • Manner, V. W.; Mayer, J. M. Concerted Proton-Electron Transfer in a Ruthenium Terpyridyl-Benzoate System with a Large Separation between the Redox and Basic Sites J. Am. Chem. Soc. 2009, 131, 9874-9875
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 9874-9875
    • Manner, V.W.1    Mayer, J.M.2
  • 10
    • 78650626762 scopus 로고    scopus 로고
    • The Thermochemistry of Proton-Coupled Electron Transfer Reactions and its Implications
    • ASAP (DOI: 10.1021/cr100085k).
    • Warren, J. J.; Tronic, T. A.; Mayer, J. M. The Thermochemistry of Proton-Coupled Electron Transfer Reactions and its Implications. Chem. Rev., ASAP (DOI: 10.1021/cr100085k).
    • Chem. Rev.
    • Warren, J.J.1    Tronic, T.A.2    Mayer, J.M.3
  • 11
    • 24744438878 scopus 로고    scopus 로고
    • Electrochemical Approach to Concerted Proton and Electron Transfers. Reduction of the Water-Superoxide Ion Complex
    • Costentin, C.; Evans, D. H.; Robert, M.; Savéant, J.-M. Electrochemical Approach to Concerted Proton and Electron Transfers. Reduction of the Water-Superoxide Ion Complex J. Am. Chem. Soc. 2005, 127, 12490-12491
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 12490-12491
    • Costentin, C.1    Evans, D.H.2    Robert, M.3    Savéant, J.-M.4
  • 12
    • 18844424175 scopus 로고
    • Inertia and Driving Force of Chemical Reactions
    • Evans, M. G.; Polanyi, M. Inertia and Driving Force of Chemical Reactions Trans. Faraday Soc. 1938, 34, 11-24
    • (1938) Trans. Faraday Soc. , vol.34 , pp. 11-24
    • Evans, M.G.1    Polanyi, M.2
  • 13
    • 16244381132 scopus 로고    scopus 로고
    • 2+ Occur by Hydrogen-Atom Transfer Rather than by Hydride Transfer
    • 2+ Occur by Hydrogen-Atom Transfer Rather than by Hydride Transfer Inorg. Chem. 2005, 44, 2150-2157
    • (2005) Inorg. Chem. , vol.44 , pp. 2150-2157
    • Matsuo, T.1    Mayer, J.M.2
  • 16
    • 0030768537 scopus 로고    scopus 로고
    • Uncatalyzed Transfer Hydrogenation and Transfer Hydrogenolysis: Two Novel Types of Hydrogen-Transfer Reactions
    • Rüchardt, C.; Gerst, M.; Ebenhoch, J. Uncatalyzed Transfer Hydrogenation and Transfer Hydrogenolysis: Two Novel Types of Hydrogen-Transfer Reactions Angew. Chem., Int. Ed. Engl. 1997, 36, 1406-1430
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1406-1430
    • Rüchardt, C.1    Gerst, M.2    Ebenhoch, J.3
  • 17
    • 0020147079 scopus 로고
    • Which Factors Determine the Reactivity and Regioselectivity of Free Radical Substitution and Addition Reactions
    • Tedder, J. M. Which Factors Determine the Reactivity and Regioselectivity of Free Radical Substitution and Addition Reactions Angew. Chem., Int. Ed. Engl. 1982, 21, 401-410
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 401-410
    • Tedder, J.M.1
  • 18
    • 0035930772 scopus 로고    scopus 로고
    • Application of the Marcus Cross Relation to Hydrogen Atom Transfer Reactions
    • Roth, J. P.; Yoder, J. C.; Won, T.-J.; Mayer, J. M. Application of the Marcus Cross Relation to Hydrogen Atom Transfer Reactions Science 2001, 294, 2524-2526
    • (2001) Science , vol.294 , pp. 2524-2526
    • Roth, J.P.1    Yoder, J.C.2    Won, T.-J.3    Mayer, J.M.4
  • 20
    • 84976413581 scopus 로고
    • Theory of Electron Transfer Reactions: Insights and Hindsights
    • Sutin, N. Theory of Electron Transfer Reactions: Insights and Hindsights Prog. Inorg. Chem. 1983, 30, 441-498
    • (1983) Prog. Inorg. Chem. , vol.30 , pp. 441-498
    • Sutin, N.1
  • 21
    • 78751516494 scopus 로고    scopus 로고
    • See references in ref 2.
    • See references in ref 2.
  • 22
    • 0012818340 scopus 로고
    • On the Slope of Free Energy Plots in Chemical Kinetics
    • Cohen, A. O.; Marcus, R. A. On the Slope of Free Energy Plots in Chemical Kinetics J. Phys. Chem. 1968, 72, 4249-4256
    • (1968) J. Phys. Chem. , vol.72 , pp. 4249-4256
    • Cohen, A.O.1    Marcus, R.A.2
  • 23
    • 34547245308 scopus 로고    scopus 로고
    • H and Other Transfers in Enzymes and in Solution: Theory and Computations, a Unified View. 2. Applications to Experiment and Computations
    • Marcus, R. A. H and Other Transfers in Enzymes and in Solution: Theory and Computations, a Unified View. 2. Applications to Experiment and Computations J. Phys. Chem. B 2007, 111, 6643-6654
    • (2007) J. Phys. Chem. B , vol.111 , pp. 6643-6654
    • Marcus, R.A.1
  • 24
    • 55649104328 scopus 로고    scopus 로고
    • Hydrogen Atom Transfer Reactions of a Ruthenium Imidazole Complex: Hydrogen Tunneling and the Applicability of the Marcus Cross Relation
    • Wu, A.; Mayer, J. M. Hydrogen Atom Transfer Reactions of a Ruthenium Imidazole Complex: Hydrogen Tunneling and the Applicability of the Marcus Cross Relation J. Am. Chem. Soc. 2008, 130, 14745-14754
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 14745-14754
    • Wu, A.1    Mayer, J.M.2
  • 25
    • 0005475211 scopus 로고
    • Abstraction of the hydroxylic hydrogen of alcohols by alkoxy radicals
    • Griller, D.; Ingold, K. U. Abstraction of the hydroxylic hydrogen of alcohols by alkoxy radicals J. Am. Chem. Soc. 1974, 96, 630-632
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 630-632
    • Griller, D.1    Ingold, K.U.2
  • 26
    • 0343457670 scopus 로고
    • A Kinetic Electron Spin Resonance Study of the Transfer of a Hydrogen Atom from α-Tetralin Hydroperoxide to a Tertiary Alkylperoxy Radical
    • Chenier, J. H. B.; Howard, J. A. A Kinetic Electron Spin Resonance Study of the Transfer of a Hydrogen Atom from α-Tetralin Hydroperoxide to a Tertiary Alkylperoxy Radical Can. J. Chem. 1975, 53, 623-627
    • (1975) Can. J. Chem. , vol.53 , pp. 623-627
    • Chenier, J.H.B.1    Howard, J.A.2
  • 27
    • 37049119763 scopus 로고
    • The Reaction of Benzyl Radicals with m -Deuteriotoluene
    • Jackson, R. A.; O'Neill, D. W. The Reaction of Benzyl Radicals with m -Deuteriotoluene J. Chem. Soc., Chem. Commun. 1969, 1210-1211
    • (1969) J. Chem. Soc., Chem. Commun. , pp. 1210-1211
    • Jackson, R.A.1    O'Neill, D.W.2
  • 28
    • 17744371869 scopus 로고    scopus 로고
    • Factors Controlling the Barriers to Degenerate Hydrogen Atom Transfers
    • references therein
    • Isborn, C.; Hrovat, D. A.; Borden, W. T.; Mayer, J. M.; Carpenter, B. K. Factors Controlling the Barriers to Degenerate Hydrogen Atom Transfers J. Am. Chem. Soc. 2005, 127, 5794-5795 and references therein
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5794-5795
    • Isborn, C.1    Hrovat, D.A.2    Borden, W.T.3    Mayer, J.M.4    Carpenter, B.K.5
  • 29
    • 0001557504 scopus 로고
    • Rate constants for degenerate hydrogen atom exchange between α-hydroxy radicals and ketones
    • Wagner, P. J.; Zhang, Y.; Puchalski, A. E. Rate constants for degenerate hydrogen atom exchange between α-hydroxy radicals and ketones J. Phys. Chem. 1993, 97, 13368-13374
    • (1993) J. Phys. Chem. , vol.97 , pp. 13368-13374
    • Wagner, P.J.1    Zhang, Y.2    Puchalski, A.E.3
  • 30
    • 21944432511 scopus 로고    scopus 로고
    • Theoretical Perspective on the Structure and Mechanism of Cytochrome P450 Enzymes
    • Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Theoretical Perspective on the Structure and Mechanism of Cytochrome P450 Enzymes Chem. Rev. 2005, 105, 2279-2328
    • (2005) Chem. Rev. , vol.105 , pp. 2279-2328
    • Shaik, S.1    Kumar, D.2    De Visser, S.P.3    Altun, A.4    Thiel, W.5
  • 31
    • 0141905366 scopus 로고    scopus 로고
    • Electron and Hydrogen-Atom Self-Exchange Reactions of Iron and Cobalt Coordination Complexes
    • Yoder, J. C.; Roth, J. P.; Gussenhoven, E. M.; Larsen, A. S.; Mayer, J. M. Electron and Hydrogen-Atom Self-Exchange Reactions of Iron and Cobalt Coordination Complexes J. Am. Chem. Soc. 2003, 125, 2629-2640
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2629-2640
    • Yoder, J.C.1    Roth, J.P.2    Gussenhoven, E.M.3    Larsen, A.S.4    Mayer, J.M.5
  • 33
    • 3042811583 scopus 로고    scopus 로고
    • Hydrogen Atom Transfer from Iron(II)-Tris[2,2'-bi(tetrahydropyrimidine)] to TEMPO: A Negative Enthalpy of Activation Predicted by the Marcus Equation
    • Mader, E. A.; Larsen, A. S.; Mayer, J. M. Hydrogen Atom Transfer from Iron(II)-Tris[2,2'-bi(tetrahydropyrimidine)] to TEMPO: A Negative Enthalpy of Activation Predicted by the Marcus Equation J. Am. Chem. Soc. 2004, 126, 8066-8067
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8066-8067
    • Mader, E.A.1    Larsen, A.S.2    Mayer, J.M.3
  • 34
    • 0000499739 scopus 로고
    • Electron-transfer reactions with unusual activation parameters. Treatment of reactions accompanied by large entropy decreases
    • Marcus, R. A.; Sutin, N. Electron-transfer reactions with unusual activation parameters. Treatment of reactions accompanied by large entropy decreases Inorg. Chem. 1975, 14, 213-216
    • (1975) Inorg. Chem. , vol.14 , pp. 213-216
    • Marcus, R.A.1    Sutin, N.2
  • 35
    • 34247515508 scopus 로고    scopus 로고
    • Large Ground-State Entropy Changes for Hydrogen Atom Transfer Reactions of Iron Complexes
    • Mader, E. A.; Davidson, E. R.; Mayer, J. M. Large Ground-State Entropy Changes for Hydrogen Atom Transfer Reactions of Iron Complexes J. Am. Chem. Soc. 2007, 129, 5153-5166
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 5153-5166
    • Mader, E.A.1    Davidson, E.R.2    Mayer, J.M.3
  • 36
    • 67749084443 scopus 로고    scopus 로고
    • Trends in Ground-State Entropies for Transition Metal Based Hydrogen Atom Transfer Reactions
    • Mader, E. A.; Manner, V. W.; Markle, T. F.; Wu, A.; Franz, J. A.; Mayer, J. M. Trends in Ground-State Entropies for Transition Metal Based Hydrogen Atom Transfer Reactions J. Am. Chem. Soc. 2009, 131, 4335-4345
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 4335-4345
    • Mader, E.A.1    Manner, V.W.2    Markle, T.F.3    Wu, A.4    Franz, J.A.5    Mayer, J.M.6
  • 38
    • 77349099243 scopus 로고    scopus 로고
    • C-H Bond Activations by Metal Oxo Compounds
    • Gunay, A.; Theopold, K. H. C-H Bond Activations by Metal Oxo Compounds Chem. Rev. 2010, 110, 1060-1081
    • (2010) Chem. Rev. , vol.110 , pp. 1060-1081
    • Gunay, A.1    Theopold, K.H.2
  • 40
    • 77950994104 scopus 로고    scopus 로고
    • The Importance of Precursor and Successor Complex Formation in a Bimolecular Proton-Electron Transfer Reaction
    • Mader, E. A.; Mayer, J. M. The Importance of Precursor and Successor Complex Formation in a Bimolecular Proton-Electron Transfer Reaction Inorg. Chem. 2010, 49, 3685-3687
    • (2010) Inorg. Chem. , vol.49 , pp. 3685-3687
    • Mader, E.A.1    Mayer, J.M.2
  • 41
    • 0141888581 scopus 로고    scopus 로고
    • Slow Hydrogen Atom Self-Exchange between Os(IV) Anilide and Os(III) Aniline Complexes: Relationships with Electron and Proton Transfer Self-Exchange
    • Soper, J. D.; Kaminsky, W.; Mayer, J. M. Slow Hydrogen Atom Self-Exchange between Os(IV) Anilide and Os(III) Aniline Complexes: Relationships with Electron and Proton Transfer Self-Exchange J. Am. Chem. Soc. 2003, 125, 12217-12229
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12217-12229
    • Soper, J.D.1    Kaminsky, W.2    Mayer, J.M.3
  • 42
    • 69049090847 scopus 로고    scopus 로고
    • Nitroxyl Radical Plus Hydroxylamine Pseudo Self-Exchange Reactions: Tunneling in Hydrogen Atom Transfer
    • Wu, A.; Mader, E. A.; Datta, A.; Hrovat, D. A.; Borden, W. T.; Mayer, J. M. Nitroxyl Radical Plus Hydroxylamine Pseudo Self-Exchange Reactions: Tunneling in Hydrogen Atom Transfer J. Am. Chem. Soc. 2009, 131, 11985-11997
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 11985-11997
    • Wu, A.1    Mader, E.A.2    Datta, A.3    Hrovat, D.A.4    Borden, W.T.5    Mayer, J.M.6
  • 43
    • 72949105323 scopus 로고    scopus 로고
    • Theory of Proton-Coupled Electron Transfer in Energy Conversion Processes
    • Hammes-Schiffer, S. Theory of Proton-Coupled Electron Transfer in Energy Conversion Processes Acc. Chem. Res. 2009, 42, 1881-1889
    • (2009) Acc. Chem. Res. , vol.42 , pp. 1881-1889
    • Hammes-Schiffer, S.1
  • 44
    • 34247143185 scopus 로고    scopus 로고
    • Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals
    • Litwinienko, G.; Ingold, K. U. Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals Acc. Chem. Res. 2007, 40, 222-230
    • (2007) Acc. Chem. Res. , vol.40 , pp. 222-230
    • Litwinienko, G.1    Ingold, K.U.2
  • 45
    • 37049073393 scopus 로고
    • Hydrogen Bonding. Part 10. A Scale of Solute Hydrogen-bond Basicity Using log K Values for Complexation in Tetrachloromethane
    • Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. Hydrogen Bonding. Part 10. A Scale of Solute Hydrogen-bond Basicity Using log K Values for Complexation in Tetrachloromethane J. Chem. Soc., Perkin Trans. 2 1990, 521-529
    • (1990) J. Chem. Soc., Perkin Trans. 2 , pp. 521-529
    • Abraham, M.H.1    Grellier, P.L.2    Prior, D.V.3    Morris, J.J.4    Taylor, P.J.5
  • 46
    • 77950411609 scopus 로고    scopus 로고
    • Predicting Organic Hydrogen Atom Transfer Rate Constants Using the Marcus Cross Relation
    • Warren, J. J.; Mayer, J. M. Predicting Organic Hydrogen Atom Transfer Rate Constants Using the Marcus Cross Relation Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 5282-5287
    • (2010) Proc. Natl. Acad. Sci. U.S.A. , vol.107 , pp. 5282-5287
    • Warren, J.J.1    Mayer, J.M.2
  • 47
    • 0037130656 scopus 로고    scopus 로고
    • Proton-Coupled Electron Transfer versus Hydrogen Atom Transfer in Benzyl/Toluene, Methoxyl/Methanol, and Phenoxyl/Phenol Self-Exchange Reactions
    • Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. Proton-Coupled Electron Transfer versus Hydrogen Atom Transfer in Benzyl/Toluene, Methoxyl/Methanol, and Phenoxyl/Phenol Self-Exchange Reactions J. Am. Chem. Soc. 2002, 124, 11142-11147
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11142-11147
    • Mayer, J.M.1    Hrovat, D.A.2    Thomas, J.L.3    Borden, W.T.4


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