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Volumn 46, Issue 11, 2013, Pages 2567-2575

Myths about the proton. The nature of H+ in condensed media

Author keywords

[No Author keywords available]

Indexed keywords

PROTON; SOLVENT; WATER;

EID: 84888634415     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar400064q     Document Type: Article
Times cited : (115)

References (68)
  • 1
    • 0003174106 scopus 로고
    • Names for Hydrogen Atoms, Ions and Groups, and for Reactions Involving Them
    • IUPAC
    • IUPAC Names for Hydrogen Atoms, Ions and Groups, and for Reactions Involving Them Pure Appl. Chem. 1988, 60, 1115-1116
    • (1988) Pure Appl. Chem. , vol.60 , pp. 1115-1116
  • 4
    • 74449085230 scopus 로고    scopus 로고
    • Proton transfer in catalysis and the role of proton shuttles in carbonic anhydrase
    • Mikulski, R. L.; Silverman, D. N. Proton transfer in catalysis and the role of proton shuttles in carbonic anhydrase Biochim. Biophys. Acta, Proteins Proteomics 2010, 1804, 422-426
    • (2010) Biochim. Biophys. Acta, Proteins Proteomics , vol.1804 , pp. 422-426
    • Mikulski, R.L.1    Silverman, D.N.2
  • 5
    • 33749052047 scopus 로고    scopus 로고
    • Chance and Design-Proton Transfer in Water, Channels and Bioenergetic Proteins
    • Wraight, C. A. Chance and Design-Proton Transfer in Water, Channels and Bioenergetic Proteins Biochim. Biophys. Acta, Bioenerg. 2006, 1757, 886-912
    • (2006) Biochim. Biophys. Acta, Bioenerg. , vol.1757 , pp. 886-912
    • Wraight, C.A.1
  • 7
    • 79960115005 scopus 로고    scopus 로고
    • Theoretical Study of O-O Single Bond Formation in the Oxidation of Water by the Ruthenium Blue Dimer
    • Bianco, R.; Hay, P. J.; Hynes, J. T. Theoretical Study of O-O Single Bond Formation in the Oxidation of Water by the Ruthenium Blue Dimer J. Phys. Chem. A 2011, 115, 8003-8016
    • (2011) J. Phys. Chem. A , vol.115 , pp. 8003-8016
    • Bianco, R.1    Hay, P.J.2    Hynes, J.T.3
  • 8
    • 79951892148 scopus 로고    scopus 로고
    • Molecular Electrocatalysts for the Oxidation of Hydrogen and the Production of Hydrogen-The Role of Pendant Amines as Proton Relays
    • DuBois, D. L.; Bullock, R. M. Molecular Electrocatalysts for the Oxidation of Hydrogen and the Production of Hydrogen-The Role of Pendant Amines as Proton Relays Eur. J. Inorg. Chem. 2011, 1017-1027
    • (2011) Eur. J. Inorg. Chem. , pp. 1017-1027
    • Dubois, D.L.1    Bullock, R.M.2
  • 9
    • 84872103087 scopus 로고    scopus 로고
    • 2 by Pyridine: Proton Relay in Aqueous Solvent and Aromatic Stabilization
    • 2 by Pyridine: Proton Relay in Aqueous Solvent and Aromatic Stabilization J. Am. Chem. Soc. 2013, 135, 142-154
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 142-154
    • Lim, C.-H.1    Holder, A.M.2    Musgrave, C.B.3
  • 15
    • 84888592155 scopus 로고    scopus 로고
    • Hydrogen bonding versus hyperconjugation in condensed-phase carbocations
    • Reed, C. A.; Stoyanov, E. S.; Tham, F. S. Hydrogen bonding versus hyperconjugation in condensed-phase carbocations Org. Biomol. Chem. 2013, 11, 3797-3802
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 3797-3802
    • Reed, C.A.1    Stoyanov, E.S.2    Tham, F.S.3
  • 16
    • 0001957353 scopus 로고
    • Proton Transfer, Acid-Base Catalysis, and Enzymatic Hydrolysis. Part I: Elementary Processes
    • Eigen, M. Proton Transfer, Acid-Base Catalysis, and Enzymatic Hydrolysis. Part I: Elementary Processes Angew. Chem., Int. Ed. 1964, 3, 1-19
    • (1964) Angew. Chem., Int. Ed. , vol.3 , pp. 1-19
    • Eigen, M.1
  • 20
    • 33947316132 scopus 로고
    • Fluorosulfuric Acid and Related Superacid Media
    • Gillespie, R. J. Fluorosulfuric Acid and Related Superacid Media Acc. Chem. Res. 1968, 1, 202-209
    • (1968) Acc. Chem. Res. , vol.1 , pp. 202-209
    • Gillespie, R.J.1
  • 23
    • 31044434755 scopus 로고    scopus 로고
    • Why Are Carborane Acids so Acidic? An Electrostatic Interpretation of Brønsted Acid Strengths
    • Balanarayan, P.; Gadre, S. R. Why Are Carborane Acids so Acidic? An Electrostatic Interpretation of Brønsted Acid Strengths Inorg. Chem. 2005, 44, 9613-9615
    • (2005) Inorg. Chem. , vol.44 , pp. 9613-9615
    • Balanarayan, P.1    Gadre, S.R.2
  • 25
    • 0000411953 scopus 로고
    • Acidity Functions from Carbon-13 NMR
    • Fărcaşiu, D.; Ghenciu, A. Acidity Functions from Carbon-13 NMR J. Am. Chem. Soc. 1993, 115, 10901-10908
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10901-10908
    • Faìrcaşiu, D.1    Ghenciu, A.2
  • 26
    • 33745728222 scopus 로고    scopus 로고
    • An Infrared μ-N-H Scale for Weakly Basic Anions. Implications for Single Molecule Acidity and Superacidity
    • Stoyanov, E. S.; Kim, K.-C.; Reed, C. A. An Infrared μ-N-H Scale for Weakly Basic Anions. Implications for Single Molecule Acidity and Superacidity J. Am. Chem. Soc. 2006, 128, 8500-8508
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 8500-8508
    • Stoyanov, E.S.1    Kim, K.-C.2    Reed, C.A.3
  • 27
    • 70449585198 scopus 로고    scopus 로고
    • Gas-Phase Bronsted Superacidity of Some Derivatives of Monocarba-closo-Borates: A Computational Study
    • Lipping, L.; Leito, I.; Koppel, I.; Koppel, I. A. Gas-Phase Bronsted Superacidity of Some Derivatives of Monocarba-closo-Borates: A Computational Study J. Phys. Chem. A 2009, 113, 12972-12978
    • (2009) J. Phys. Chem. A , vol.113 , pp. 12972-12978
    • Lipping, L.1    Leito, I.2    Koppel, I.3    Koppel, I.A.4
  • 28
    • 72449160645 scopus 로고    scopus 로고
    • Investigating the Weak to Evaluate the Strong: An Experimental Determination of the Electron Binding Energy of Carborane Anions and the Gas phase Acidity of Carborane Acids
    • Meyer, M. M.; Wang, X.-B.; Reed, C. A.; Wang, L.-S.; Kass, S. R. Investigating the Weak to Evaluate the Strong: An Experimental Determination of the Electron Binding Energy of Carborane Anions and the Gas phase Acidity of Carborane Acids J. Am. Chem. Soc. 2009, 131, 18050-18051
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18050-18051
    • Meyer, M.M.1    Wang, X.-B.2    Reed, C.A.3    Wang, L.-S.4    Kass, S.R.5
  • 29
    • 17144408314 scopus 로고    scopus 로고
    • Carborane acids. New "strong yet gentle" acids for organic and inorganic chemistry
    • Reed, C. A. Carborane acids. New "strong yet gentle" acids for organic and inorganic chemistry Chem. Commun. 2005, 1669-1677
    • (2005) Chem. Commun. , pp. 1669-1677
    • Reed, C.A.1
  • 32
    • 64149089396 scopus 로고    scopus 로고
    • New kinds of organic superacids. Bis(perfluoroalkylsulfonylimino)- trifluoromethanesulfonic acids and their trimethylsilyl esters
    • Posternak, A. G.; Garlyauskayte, R. Y.; Polovinko, V. V.; Lev M. Yagupolskii, L. M.; Yagupolskii, Y. L. New kinds of organic superacids. Bis(perfluoroalkylsulfonylimino)-trifluoromethanesulfonic acids and their trimethylsilyl esters Org. Biomol. Chem. 2009, 7, 1642-1645
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 1642-1645
    • Posternak, A.G.1    Garlyauskayte, R.Y.2    Polovinko, V.V.3    Lev, M.4    Yagupolskii, L.M.5    Yagupolskii, Y.L.6
  • 33
    • 70450185933 scopus 로고    scopus 로고
    • Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Brønsted Acids
    • Tian, Z.; Fattahi, A.; Lis, L.; Kass, S. R. Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Brønsted Acids J. Am. Chem. Soc. 2009, 131, 16984-16988
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16984-16988
    • Tian, Z.1    Fattahi, A.2    Lis, L.3    Kass, S.R.4
  • 40
    • 79957992398 scopus 로고    scopus 로고
    • Oligomeric Carbocation-like Species from Protonation of Chloroalkanes
    • Stoyanov, E. S.; Stoyanova, I. V.; Reed, C. A. Oligomeric Carbocation-like Species from Protonation of Chloroalkanes J. Am. Chem. Soc. 2011, 133, 8452-8454
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8452-8454
    • Stoyanov, E.S.1    Stoyanova, I.V.2    Reed, C.A.3
  • 42
    • 77956715871 scopus 로고
    • Hydrogen Bonding and Chemical Reactivity
    • Hibbert, F.; Emsley, J. Hydrogen Bonding and Chemical Reactivity Adv. Phys. Org. Chem. 1991, 26, 255-379
    • (1991) Adv. Phys. Org. Chem. , vol.26 , pp. 255-379
    • Hibbert, F.1    Emsley, J.2
  • 43
    • 0028769661 scopus 로고
    • Symmetries of hydrogen bonds in solution
    • Perrin, C. L. Symmetries of hydrogen bonds in solution Science 1994, 266, 1665-1668
    • (1994) Science , vol.266 , pp. 1665-1668
    • Perrin, C.L.1
  • 44
    • 0011438965 scopus 로고
    • +: A convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes
    • +: A convenient reagent for generation and stabilization of cationic, highly electrophilic organometallic complexes Organometallics 1992, 11, 3920-3922
    • (1992) Organometallics , vol.11 , pp. 3920-3922
    • Brookhart, M.1    Grant, B.2    Volpe Jr., A.F.3
  • 47
    • 84857617137 scopus 로고    scopus 로고
    • Interaction of acetonitrile with trifluoromethanesulfonic acid: Unexpected formation of a wide variety of structures
    • Salnikov, G. E.; Genaev, A. M.; Vasiliev, V. G.; Shubin, V. G. Interaction of acetonitrile with trifluoromethanesulfonic acid: unexpected formation of a wide variety of structures Org. Biomol. Chem. 2012, 10, 2282-2288
    • (2012) Org. Biomol. Chem. , vol.10 , pp. 2282-2288
    • Salnikov, G.E.1    Genaev, A.M.2    Vasiliev, V.G.3    Shubin, V.G.4
  • 49
    • 0000752297 scopus 로고
    • + Hydronium Ion with a Weakly Coordinating Anion
    • + Hydronium Ion with a Weakly Coordinating Anion Inorg. Chem. 1995, 34, 5403-5404
    • (1995) Inorg. Chem. , vol.34 , pp. 5403-5404
    • Xie, Z.1    Bau, R.2    Reed, C.A.3
  • 50
    • 78650460393 scopus 로고    scopus 로고
    • Are Short, Low-Barrier Hydrogen Bonds Unusually Strong?
    • Perrin, C. L. Are Short, Low-Barrier Hydrogen Bonds Unusually Strong? Acc. Chem. Res. 2010, 43, 1550-1557
    • (2010) Acc. Chem. Res. , vol.43 , pp. 1550-1557
    • Perrin, C.L.1
  • 51
    • 34247356978 scopus 로고    scopus 로고
    • Quantum Structure of the Intermolecular Proton Bond
    • Roscioli, J. R.; McCunn, L. R.; Johnson, M. A. Quantum Structure of the Intermolecular Proton Bond Science 2007, 316, 249-254
    • (2007) Science , vol.316 , pp. 249-254
    • Roscioli, J.R.1    Mccunn, L.R.2    Johnson, M.A.3
  • 54
    • 7544222924 scopus 로고    scopus 로고
    • A Strong Acid that does not Protonate Water
    • Stoyanov, E. S.; Kim, K.-C.; Reed, C. A. A Strong Acid that does not Protonate Water J. Phys. Chem. A 2004, 108, 9310-9315
    • (2004) J. Phys. Chem. A , vol.108 , pp. 9310-9315
    • Stoyanov, E.S.1    Kim, K.-C.2    Reed, C.A.3
  • 55
    • 33244460861 scopus 로고    scopus 로고
    • + Hydronium Ion in Benzene and Chlorinated Hydrocarbon Solvents. Conditions of Existence and Reinterpretation of Infrared Data
    • + Hydronium Ion in Benzene and Chlorinated Hydrocarbon Solvents. Conditions of Existence and Reinterpretation of Infrared Data J. Am. Chem. Soc. 2006, 128, 1948-1958
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1948-1958
    • Stoyanov, E.S.1    Kim, K.-C.2    Reed, C.A.3
  • 62
    • 33644989063 scopus 로고    scopus 로고
    • Computer Simulation of Proton Solvation and Transport in Aqueous and Biomolecular Systems
    • Voth, G. A. Computer Simulation of Proton Solvation and Transport in Aqueous and Biomolecular Systems Acc. Chem. Res. 2006, 39, 143-150
    • (2006) Acc. Chem. Res. , vol.39 , pp. 143-150
    • Voth, G.A.1
  • 63
    • 37049120085 scopus 로고
    • Hydrogen Bonding in Some Adducts of Oxygen Bases with Acids. Part II. Infrared Spectra of Liquid Adducts of Carboxylic Acids with Sulphoxides, Phosphine Oxides, and Other Bases N
    • Hadži, D.; Kobilarov Hydrogen Bonding in Some Adducts of Oxygen Bases with Acids. Part II. Infrared Spectra of Liquid Adducts of Carboxylic Acids with Sulphoxides, Phosphine Oxides, and Other Bases N J. Chem. Soc. A 1966, 439-445
    • (1966) J. Chem. Soc. A , pp. 439-445
    • Hadži, D.1    Kobilarov2
  • 64
    • 33746282813 scopus 로고    scopus 로고
    • The Molecular Origin of the "Continuous" Infrared Absorption in Aqueous Solutions of Acids: A Computational Approach
    • Iftimie, R.; Tuckerman, M. E. The Molecular Origin of the "Continuous" Infrared Absorption in Aqueous Solutions of Acids: A Computational Approach Angew. Chem., Int. Ed. 2006, 45, 1144-1147
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1144-1147
    • Iftimie, R.1    Tuckerman, M.E.2
  • 65
    • 48749141039 scopus 로고
    • + ions in glassy aqueous HX solutions (X = Cl and Br)
    • + ions in glassy aqueous HX solutions (X = Cl and Br) Chem. Phys. Lett. 1984, 107, 438-441
    • (1984) Chem. Phys. Lett. , vol.107 , pp. 438-441
    • Kanno, H.1    Hiraishi, J.2
  • 66
    • 33847086871 scopus 로고
    • When is an intermediate not an intermediate? Enforced mechanisms of general acid-base catalyzed, carbocation, carbanion, and ligand exchange reactions
    • Jencks, W. P. When is an intermediate not an intermediate? Enforced mechanisms of general acid-base catalyzed, carbocation, carbanion, and ligand exchange reactions Acc. Chem. Res. 1980, 13, 161-169
    • (1980) Acc. Chem. Res. , vol.13 , pp. 161-169
    • Jencks, W.P.1
  • 67
    • 84055211882 scopus 로고    scopus 로고
    • Greatly Under-Appreciated Fundamental Principle of Physical Organic Chemistry
    • Cox, R. A. A Greatly Under-Appreciated Fundamental Principle of Physical Organic Chemistry Int. J. Mol. Sci. 2011, 12, 8316-8332
    • (2011) Int. J. Mol. Sci. , vol.12 , pp. 8316-8332
    • Cox, R.A.A.1
  • 68
    • 0000135791 scopus 로고
    • Ab initio molecular dynamics simulation of the solvation and transport of hydronium and hydroxyl ions in water
    • Tuckerman, M.; Laasonen, K.; Sprik, M.; Parrinello, M. Ab initio molecular dynamics simulation of the solvation and transport of hydronium and hydroxyl ions in water J. Chem. Phys. 1995, 103, 150-161
    • (1995) J. Chem. Phys. , vol.103 , pp. 150-161
    • Tuckerman, M.1    Laasonen, K.2    Sprik, M.3    Parrinello, M.4


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