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Volumn 117, Issue 49, 2013, Pages 15290-15296

Toward organic photohydrides: Excited-state behavior of 10-methyl-9-phenyl-9,10-dihydroacridine

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE/WATER MIXTURES; COMPUTATIONAL METHODOLOGY; CONCERTED MECHANISM; ELECTRON RELEASE; HYDROGEN ATOMS; ORGANIC HYDRIDES; THERMODYNAMIC PARAMETER; TRANSFER MECHANISMS;

EID: 84890458018     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp401770e     Document Type: Article
Times cited : (22)

References (53)
  • 1
    • 0011618952 scopus 로고
    • Nicotinamide-adenine-dinucleotide. 2 nd ed. Walter de Gruyer: New York.
    • Nicotinamide-adenine-dinucleotide. Concise Encyclo-pedia Biochemistry, 2 nd ed.; Walter de Gruyer: New York, 1988.
    • (1988) Concise Encyclo-pedia Biochemistry
  • 2
    • 0032761362 scopus 로고    scopus 로고
    • Which Hydrogen Atom Is First Transferred in the NAD(P)H Model Hantzsch Ester Mediated Reactions via One-Step and Multistep Hydride Transfer?
    • Zhu, X. Q.; Liu, Y. C.; Cheng, J. P. Which Hydrogen Atom Is First Transferred in the NAD(P)H Model Hantzsch Ester Mediated Reactions via One-Step and Multistep Hydride Transfer? J. Org. Chem. 1999, 64, 8980-8981
    • (1999) J. Org. Chem. , vol.64 , pp. 8980-8981
    • Zhu, X.Q.1    Liu, Y.C.2    Cheng, J.P.3
  • 3
    • 0034286445 scopus 로고    scopus 로고
    • A Detailed Investigation into the Oxidation Mechanism of Hantzsch 1,4-Dihydropyridines by Ethyl α-Cyanocinnamates and Benzylidenemalononitriles
    • Zhu, X. Q.; Zou, H. L.; Yuan, P. W.; Liu, Y.; Cao, L.; Cheng, J. P. A Detailed Investigation into the Oxidation Mechanism of Hantzsch 1,4-Dihydropyridines by Ethyl α-Cyanocinnamates and Benzylidenemalononitriles J. Chem. Soc., Perkin Trans. 2 2000, 1857-1861
    • (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 1857-1861
    • Zhu, X.Q.1    Zou, H.L.2    Yuan, P.W.3    Liu, Y.4    Cao, L.5    Cheng, J.P.6
  • 4
    • 0242660859 scopus 로고    scopus 로고
    • Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester
    • Simon, J.; Guimarães, C. R. W.; Corréa, M. B.; de Oliveira, C. A. F.; da Cunha Pinto, A.; de Alencastro, R. B. Synthetic and Theoretical Studies on the Reduction of Electron Withdrawing Group Conjugated Olefins Using the Hantzsch 1,4-Dihydropyridine Ester J. Org. Chem. 2003, 68, 8815-8822
    • (2003) J. Org. Chem. , vol.68 , pp. 8815-8822
    • Simon, J.1    Guimarães, C.R.W.2    Corréa, M.B.3    De Oliveira, C.A.F.4    Da Cunha Pinto, A.5    De Alencastro, R.B.6
  • 5
    • 0001099145 scopus 로고
    • General Acid Catalysis of the Reduction of p-Benzoquinone by an NADH Analog. Evidence for Concerted Hydride and Hydron Transfer
    • Coleman, C. A.; Rose, J. G.; Murray, C. J. General Acid Catalysis of the Reduction of p-Benzoquinone by an NADH Analog. Evidence for Concerted Hydride and Hydron Transfer J. Am. Chem. Soc. 1992, 114, 9755-9762
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9755-9762
    • Coleman, C.A.1    Rose, J.G.2    Murray, C.J.3
  • 6
    • 57349086283 scopus 로고    scopus 로고
    • Sequential Electron-Transfer and Proton-Transfer Pathways in Hydride-Transfer Reactions from Dihydronicotinamide Adenine Dinucleotide Analogues to Non-Heme Oxoiron (IV) Complexes and p-Chloranil. Detection of Radical Cations of NADH Analogues in Acid-Promoted Hydride-Transfer Reactions
    • Fukuzumi, S.; Kotani, H.; Lee, Y. M.; Nam, W. Sequential Electron-Transfer and Proton-Transfer Pathways in Hydride-Transfer Reactions from Dihydronicotinamide Adenine Dinucleotide Analogues to Non-Heme Oxoiron (IV) Complexes and p-Chloranil. Detection of Radical Cations of NADH Analogues in Acid-Promoted Hydride-Transfer Reactions J. Am. Chem. Soc. 2008, 130, 15134-15142
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 15134-15142
    • Fukuzumi, S.1    Kotani, H.2    Lee, Y.M.3    Nam, W.4
  • 7
    • 0001416648 scopus 로고
    • Electron-Transfer Oxidation of 9-Substituted 10-Methyl-9,10- Dihydroacridines. Cleavage of the Carbon-Hydrogen vs. Carbon-Carbon Bond of the Radical Cations
    • Fukuzumi, S.; Tokuda, Y.; Kitano, T.; Okamoto, T.; Otera, J. Electron-Transfer Oxidation of 9-Substituted 10-Methyl-9,10-Dihydroacridines. Cleavage of the Carbon-Hydrogen vs. Carbon-Carbon Bond of the Radical Cations J. Am. Chem. Soc. 1993, 115, 8960-8968
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8960-8968
    • Fukuzumi, S.1    Tokuda, Y.2    Kitano, T.3    Okamoto, T.4    Otera, J.5
  • 8
    • 0000303985 scopus 로고
    • On the Electron-Proton-Electron Mechanism for 1-Benzyl-1,4- dihydronicotinamide Oxidations
    • Miller, L. L.; Valentine, J. R. On the Electron-Proton-Electron Mechanism for 1-Benzyl-1,4-dihydronicotinamide Oxidations J. Am. Chem. Soc. 1988, 110, 3982-3989
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3982-3989
    • Miller, L.L.1    Valentine, J.R.2
  • 10
    • 34250823597 scopus 로고    scopus 로고
    • A Fluorescence Turn-On Mechanism to Detect High Explosives RDX and PETN
    • Andrew, T. L.; Swager, T. M. A Fluorescence Turn-On Mechanism to Detect High Explosives RDX and PETN J. Am. Chem. Soc. 2007, 129, 7254-7255
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 7254-7255
    • Andrew, T.L.1    Swager, T.M.2
  • 11
    • 53149152983 scopus 로고    scopus 로고
    • A Mechanistic Dichotomy in Concerted versus Stepwise Pathways in Hydride and Hydrogen Transfer Reactions of NADH Analogues
    • Yuasa, J.; Fukuzumi, S. A Mechanistic Dichotomy in Concerted versus Stepwise Pathways in Hydride and Hydrogen Transfer Reactions of NADH Analogues J. Phys. Org. Chem. 2008, 21, 886-896
    • (2008) J. Phys. Org. Chem. , vol.21 , pp. 886-896
    • Yuasa, J.1    Fukuzumi, S.2
  • 12
    • 0035979748 scopus 로고    scopus 로고
    • Hydrogen Produced from Hydrohalic Acid Solutions by a Two-Electron Mixed-Valence Photocatalyst
    • Heyduk, A. F.; Nocera, D. G. Hydrogen Produced from Hydrohalic Acid Solutions by a Two-Electron Mixed-Valence Photocatalyst Science 2001, 293, 1639-1641
    • (2001) Science , vol.293 , pp. 1639-1641
    • Heyduk, A.F.1    Nocera, D.G.2
  • 13
    • 80053327148 scopus 로고    scopus 로고
    • Discovering the Balance of Steric and Electronic Factors Needed to Provide a New Structural Motif for Photocatalytic Hydrogen Production from Water
    • White, T. A.; Whitaker, B. N.; Brewer, K. J. Discovering the Balance of Steric and Electronic Factors Needed to Provide a New Structural Motif for Photocatalytic Hydrogen Production from Water J. Am. Chem. Soc. 2011, 133, 15332-15334
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 15332-15334
    • White, T.A.1    Whitaker, B.N.2    Brewer, K.J.3
  • 14
    • 78149246205 scopus 로고    scopus 로고
    • Reductive Side of Water Splitting in Artificial Photosynthesis: New Homogeneous Photosystems of Great Activity and Mechanistic Insight
    • McCormick, T. M.; Calitree, B. D.; Orchard, A.; Kraut, N. D.; Bright, F. V.; Detty, M. R.; Eisenberg, R. Reductive Side of Water Splitting in Artificial Photosynthesis: New Homogeneous Photosystems of Great Activity and Mechanistic Insight J. Am. Chem. Soc. 2010, 132, 15480-15483
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 15480-15483
    • McCormick, T.M.1    Calitree, B.D.2    Orchard, A.3    Kraut, N.D.4    Bright, F.V.5    Detty, M.R.6    Eisenberg, R.7
  • 15
    • 70450169427 scopus 로고    scopus 로고
    • Structure-Activity Correlations among Iridium(III) Photosensitizers in a Robust Water-Reducing System
    • Curtin, P. N.; Tinker, L. L.; Burgess, C. M.; Cline, E. D.; Bernhard, S. Structure-Activity Correlations among Iridium(III) Photosensitizers in a Robust Water-Reducing System Inorg. Chem. 2009, 48, 10498-10506
    • (2009) Inorg. Chem. , vol.48 , pp. 10498-10506
    • Curtin, P.N.1    Tinker, L.L.2    Burgess, C.M.3    Cline, E.D.4    Bernhard, S.5
  • 17
    • 73949160670 scopus 로고    scopus 로고
    • Cobalt and Nickel Diimine-Dioxime Complexes as Molecular Electrocatalysts for Hydrogen Evolution with Low Overvoltages
    • Jacques, P. A.; Artero, V.; Pécaut, J.; Fontecave, M. Cobalt and Nickel Diimine-Dioxime Complexes as Molecular Electrocatalysts for Hydrogen Evolution with Low Overvoltages Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 20627-20632
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 20627-20632
    • Jacques, P.A.1    Artero, V.2    Pécaut, J.3    Fontecave, M.4
  • 19
    • 72949117212 scopus 로고    scopus 로고
    • Molecular Approaches to the Photocatalytic Reduction of Carbon Dioxide for Solar Fuels
    • Morris, A. J.; Meyer, G. J.; Fujita, E. Molecular Approaches to the Photocatalytic Reduction of Carbon Dioxide for Solar Fuels Acc. Chem. Res. 2009, 42, 1983-1994
    • (2009) Acc. Chem. Res. , vol.42 , pp. 1983-1994
    • Morris, A.J.1    Meyer, G.J.2    Fujita, E.3
  • 20
    • 84863980119 scopus 로고    scopus 로고
    • Mechanistic Study of the Photochemical Hydroxide Ion Release from 9-Hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine
    • Zhou, D.; Khatmullin, R.; Walpita, J.; Miller, N. A.; Luk, H. L.; Vyas, S.; Hadad, C. M.; Glusac, K. D. Mechanistic Study of the Photochemical Hydroxide Ion Release from 9-Hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine J. Am. Chem. Soc. 2012, 134, 11301-11303
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 11301-11303
    • Zhou, D.1    Khatmullin, R.2    Walpita, J.3    Miller, N.A.4    Luk, H.L.5    Vyas, S.6    Hadad, C.M.7    Glusac, K.D.8
  • 21
    • 0000395704 scopus 로고
    • Flavin Analog-Metal Ion Complexes Acting as Efficient Photocatalysts in the Oxidation of p-Methylbenzyl Alcohol by Oxygen under Irradiation with Visible Light
    • Fukuzumi, S.; Kuroda, S.; Tanaka, T. Flavin Analog-Metal Ion Complexes Acting as Efficient Photocatalysts in the Oxidation of p-Methylbenzyl Alcohol by Oxygen under Irradiation with Visible Light J. Am. Chem. Soc. 1985, 107, 3020-3027
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3020-3027
    • Fukuzumi, S.1    Kuroda, S.2    Tanaka, T.3
  • 22
    • 34247463734 scopus 로고    scopus 로고
    • On the Mechanism of Reaction of Radicals with Tirapazamine
    • Shi, X.; Mandel, S. M.; Platz, M. S. On the Mechanism of Reaction of Radicals with Tirapazamine J. Am. Chem. Soc. 2007, 129, 4542-4550
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 4542-4550
    • Shi, X.1    Mandel, S.M.2    Platz, M.S.3
  • 23
    • 40149109196 scopus 로고    scopus 로고
    • Systematic Optimization of Long-Range Corrected Hybrid Density Functionals
    • Chai, J. D.; Head-Gordon, M. Systematic Optimization of Long-Range Corrected Hybrid Density Functionals J. Chem. Phys. 2008, 128, 084106
    • (2008) J. Chem. Phys. , vol.128 , pp. 084106
    • Chai, J.D.1    Head-Gordon, M.2
  • 24
    • 55849117399 scopus 로고    scopus 로고
    • Long-Range Corrected Hybrid Density Functionals with Damped Atom-Atom Dispersion Corrections
    • Chai, J. D.; Head-Gordon, M. Long-Range Corrected Hybrid Density Functionals with Damped Atom-Atom Dispersion Corrections Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
    • (2008) Phys. Chem. Chem. Phys. , vol.10 , pp. 6615-6620
    • Chai, J.D.1    Head-Gordon, M.2
  • 25
    • 84961985847 scopus 로고    scopus 로고
    • Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model
    • Barone, V.; Cossi, M. Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model J. Phys. Chem. A 1998, 102, 1995-2001
    • (1998) J. Phys. Chem. A , vol.102 , pp. 1995-2001
    • Barone, V.1    Cossi, M.2
  • 28
    • 0343110022 scopus 로고
    • Laser Flash Photolysis and Product Studies of the Photoionization of N-Methylacridan in Aqueous Solution
    • Shukla, D.; De Rege, F.; Wan, P.; Johnston, L. J. Laser Flash Photolysis and Product Studies of the Photoionization of N-Methylacridan in Aqueous Solution J. Phys. Chem. 1991, 95, 10240-10246
    • (1991) J. Phys. Chem. , vol.95 , pp. 10240-10246
    • Shukla, D.1    De Rege, F.2    Wan, P.3    Johnston, L.J.4
  • 30
    • 37049079215 scopus 로고
    • 10,10′-Dimethyl-9,9′-biacridine Acting as a Unique Electron Source Compared with the Corresponding Monomer for the Efficient Reduction of Dioxygen, Catalysed by a Cobalt Porphyrin in the Presence of Perchloric Acid
    • Fukuzumi, S.; Yorisue, T. 10,10′-Dimethyl-9,9′-biacridine Acting as a Unique Electron Source Compared with the Corresponding Monomer for the Efficient Reduction of Dioxygen, Catalysed by a Cobalt Porphyrin in the Presence of Perchloric Acid J. Chem. Soc., Perkin Trans. 2 1991, 1607-1611
    • (1991) J. Chem. Soc., Perkin Trans. 2 , pp. 1607-1611
    • Fukuzumi, S.1    Yorisue, T.2
  • 31
    • 0033599290 scopus 로고    scopus 로고
    • ESR Spectra of Superoxide Anion-Scandium Complexes Detectable in Fluid Solution
    • Fukuzumi, S.; Patz, M.; Suenobu, T.; Kuwahara, Y.; Itoh, S. ESR Spectra of Superoxide Anion-Scandium Complexes Detectable in Fluid Solution J. Am. Chem. Soc. 1999, 121, 1605-1606
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1605-1606
    • Fukuzumi, S.1    Patz, M.2    Suenobu, T.3    Kuwahara, Y.4    Itoh, S.5
  • 33
    • 33749613476 scopus 로고    scopus 로고
    • DNA Cleavage by UVA Irradiation of NADH with Dioxygen via Radical Chain Processes
    • Tanaka, M.; Ohkubo, K.; Fukuzumi, S. DNA Cleavage by UVA Irradiation of NADH with Dioxygen via Radical Chain Processes J. Phys. Chem. A 2006, 110, 11214-11218
    • (2006) J. Phys. Chem. A , vol.110 , pp. 11214-11218
    • Tanaka, M.1    Ohkubo, K.2    Fukuzumi, S.3
  • 34
    • 0000371485 scopus 로고
    • Efficient Catalytic Systems for Electron Transfer from an NADH Model Compound to Dioxygen
    • Fukuzumi, S.; Mochizuki, S.; Tanaka, T. Efficient Catalytic Systems for Electron Transfer from an NADH Model Compound to Dioxygen Inorg. Chem. 1990, 29, 653-659
    • (1990) Inorg. Chem. , vol.29 , pp. 653-659
    • Fukuzumi, S.1    Mochizuki, S.2    Tanaka, T.3
  • 35
    • 0029097060 scopus 로고
    • Steric and Kinetic Isotope Effects in the Deprotonation of Cation Radicals of NADH Synthetic Analogs
    • Anne, A.; Fraoua, S.; Hapiot, P.; Moiroux, J.; Saveant, J. M. Steric and Kinetic Isotope Effects in the Deprotonation of Cation Radicals of NADH Synthetic Analogs J. Am. Chem. Soc. 1995, 117, 7412-7421
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7412-7421
    • Anne, A.1    Fraoua, S.2    Hapiot, P.3    Moiroux, J.4    Saveant, J.M.5
  • 37
    • 0037090831 scopus 로고    scopus 로고
    • Proton-Coupled Electron Transfer from Phosphorus: A P-H/P-D Kinetic Isotope Effect of 178
    • Huynh, M. H. V.; Meyer, T. J. Proton-Coupled Electron Transfer from Phosphorus: A P-H/P-D Kinetic Isotope Effect of 178 Angew. Chem., Int. Ed. 2002, 41, 1395-1398
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1395-1398
    • Huynh, M.H.V.1    Meyer, T.J.2
  • 38
    • 36849117004 scopus 로고
    • Spin - Orbit Coupling and the Radiationless Processes in Nitrogen Heterocyclics
    • El-Sayed, M. Spin-Orbit Coupling and the Radiationless Processes in Nitrogen Heterocyclics J. Chem. Phys. 1963, 38, 2834-2838
    • (1963) J. Chem. Phys. , vol.38 , pp. 2834-2838
    • El-Sayed, M.1
  • 43
    • 0036149612 scopus 로고    scopus 로고
    • Excited-State Proton Transfer: From Constrained Systems to "super" Photoacids to Superfast Proton Transfer
    • Tolbert, L. M.; Solntsev, K. M. Excited-State Proton Transfer: From Constrained Systems to "Super" Photoacids to Superfast Proton Transfer Acc. Chem. Res. 2002, 35, 19-27
    • (2002) Acc. Chem. Res. , vol.35 , pp. 19-27
    • Tolbert, L.M.1    Solntsev, K.M.2
  • 44
    • 0034731723 scopus 로고    scopus 로고
    • Conversion Constants for Redox Potentials Measured versus Different Reference Electrodes in Acetonitrile Solutions at 25 C
    • Pavlishchuk, V. V.; Addison, A. W. Conversion Constants for Redox Potentials Measured versus Different Reference Electrodes in Acetonitrile Solutions at 25 C Inorg. Chim. Acta 2000, 298, 97-102
    • (2000) Inorg. Chim. Acta , vol.298 , pp. 97-102
    • Pavlishchuk, V.V.1    Addison, A.W.2
  • 45
    • 77953425942 scopus 로고    scopus 로고
    • Absolute Potential of the Standard Hydrogen Electrode and the Problem of Interconversion of Potentials in Different Solvents
    • Isse, A. A.; Gennaro, A. Absolute Potential of the Standard Hydrogen Electrode and the Problem of Interconversion of Potentials in Different Solvents J. Phys. Chem. B 2010, 114, 7894-7899
    • (2010) J. Phys. Chem. B , vol.114 , pp. 7894-7899
    • Isse, A.A.1    Gennaro, A.2
  • 46
    • 0001700494 scopus 로고
    • Hydride Affinities of Organic Radicals in Solution. A Comparison of Free Radicals and Carbenium Ions as Hydride Ion Acceptors
    • Handoo, K. L.; Cheng, J. P.; Parker, V. D. Hydride Affinities of Organic Radicals in Solution. A Comparison of Free Radicals and Carbenium Ions as Hydride Ion Acceptors J. Am. Chem. Soc. 1993, 115, 5067-5072
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5067-5072
    • Handoo, K.L.1    Cheng, J.P.2    Parker, V.D.3
  • 47
    • 0025317253 scopus 로고
    • + Analogs. A Detailed Mechanistic Kinetic and Thermodynamic Analysis of the 10-Methylacridan/10-Methylacridinium Couple in Acetonitrile
    • + Analogs. A Detailed Mechanistic Kinetic and Thermodynamic Analysis of the 10-Methylacridan/10-Methylacridinium Couple in Acetonitrile J. Am. Chem. Soc. 1990, 112, 1337-1343
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 1337-1343
    • Hapiot, P.1    Moiroux, J.2    Saveant, J.M.3
  • 49
    • 0034919821 scopus 로고    scopus 로고
    • Estimates of Hydride Ion Stability in Condensed Systems: Energy of Formation and Solvation in Aqueous and Polar-Organic Solvents
    • Kelly, C. A.; Rosseinsky, D. R. Estimates of Hydride Ion Stability in Condensed Systems: Energy of Formation and Solvation in Aqueous and Polar-Organic Solvents Phys. Chem. Chem. Phys. 2001, 3, 2086-2090
    • (2001) Phys. Chem. Chem. Phys. , vol.3 , pp. 2086-2090
    • Kelly, C.A.1    Rosseinsky, D.R.2
  • 50
    • 84962374892 scopus 로고    scopus 로고
    • Hydride Donor Abilities of Cationic Transition Metal Hydrides from DFT-PCM Calculations
    • Kovács, G.; Pápai, I. Hydride Donor Abilities of Cationic Transition Metal Hydrides from DFT-PCM Calculations Organometallics 2006, 25, 820-825
    • (2006) Organometallics , vol.25 , pp. 820-825
    • Kovács, G.1    Pápai, I.2
  • 52
    • 79958202730 scopus 로고    scopus 로고
    • Toward Robust Computational Electrochemical Predicting the Environmental Fate of Organic Pollutants
    • Sviatenko, L.; Isayev, O.; Gorb, L.; Hill, F.; Leszczynski, J. Toward Robust Computational Electrochemical Predicting the Environmental Fate of Organic Pollutants J. Comput. Chem. 2011, 32, 2195-2203
    • (2011) J. Comput. Chem. , vol.32 , pp. 2195-2203
    • Sviatenko, L.1    Isayev, O.2    Gorb, L.3    Hill, F.4    Leszczynski, J.5


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