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Volumn 12, Issue 12, 2011, Pages 8316-8332

A greatly under-appreciated fundamental principle of physical organic chemistry

Author keywords

Excess acidity correlations; Intermediate; Lifetimes; Reaction mechanism

Indexed keywords

ACYLIMIDAZOLE; BENZAMIDE; CARBOCATION; CATION; ESTER; ETHER; HYDROCHLORIC ACID; IMIDAZOLE DERIVATIVE; PERCHLORIC ACID; PROTON; SULFURIC ACID; UNCLASSIFIED DRUG; WATER; ACID; ALKALI;

EID: 84055211882     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12128316     Document Type: Review
Times cited : (21)

References (80)
  • 2
    • 0000251751 scopus 로고
    • Stable carbonium ions. XCI. Carbon-13 nuclear magnetic resonance spectroscopic study of carbonium ions
    • Olah, G.A.; White, A.M. Stable carbonium ions. XCI. Carbon-13 nuclear magnetic resonance spectroscopic study of carbonium ions. J. Am. Chem. Soc. 1969, 91, 5801-5810.
    • (1969) J. Am. Chem. Soc , vol.91 , pp. 5801-5810
    • Olah, G.A.1    White, A.M.2
  • 3
    • 33748220638 scopus 로고    scopus 로고
    • My search for carbocations and their role in chemistry
    • and references therein
    • Olah, G.A. My search for carbocations and their role in chemistry. Angew. Chem. Int. Ed. Engl. 1995, 34, 1393-1405. and references therein.
    • Angew. Chem. Int. Ed. Engl , vol.34 , pp. 1393-1405
    • Olah, G.A.1
  • 4
    • 0001550713 scopus 로고
    • Stable carbocations. CXXIX. Mechanism of the Benzidine and Wallach rearrangements based on direct observation of dicationic reaction intermediates and related model compounds
    • Olah, G.A.; Dunne, K.; Kelly, D.P.; Mo, Y.K. Stable carbocations. CXXIX. Mechanism of the Benzidine and Wallach rearrangements based on direct observation of dicationic reaction intermediates and related model compounds. J. Am. Chem. Soc. 1972, 94, 7438-7447.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 7438-7447
    • Olah, G.A.1    Dunne, K.2    Kelly, D.P.3    Mo, Y.K.4
  • 5
    • 0003466969 scopus 로고
    • 4th ed.; Prentice Hall: Englewood Cliffs, NJ, USA
    • Moore, W.J. Physical Chemistry, 4th ed.; Prentice Hall: Englewood Cliffs, NJ, USA, 1972; p. 769.
    • (1972) Physical Chemistry , pp. 769
    • Moore, W.J.1
  • 6
    • 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
  • 7
    • 0035543101 scopus 로고    scopus 로고
    • Formation and stability of carbocations and carbanions in water and intrinsic barriers to their reactions
    • Richard, J.P.; Amyes, T.L.; Toteva, M.M. Formation and stability of carbocations and carbanions in water and intrinsic barriers to their reactions. Acc. Chem. Res. 2001, 34, 981-988 and references therein.
    • (2001) Acc. Chem. Res , vol.34 , pp. 981-988
    • Richard, J.P.1    Amyes, T.L.2    Toteva, M.M.3
  • 8
    • 0141751575 scopus 로고
    • Kinetics of decomposition of primary aliphatic N-nitroamines in aqueous sulfuric acid
    • Russ. J. Org. Chem. 1983, 19, 615-620
    • Vorob'eva, E.N.; Kuznetsov, L.L.; Gidaspov, B.V. Kinetics of decomposition of primary aliphatic N-nitroamines in aqueous sulfuric acid. Zh. Org. Khim. 1983, 19, 698-704; Russ. J. Org. Chem. 1983, 19, 615-620.
    • (1983) Zh. Org. Khim , vol.19 , pp. 698-704
    • Vorob'eva, E.N.1    Kuznetsov, L.L.2    Gidaspov, B.V.3
  • 9
    • 1542447550 scopus 로고
    • Oxygen exchange into 2-butanol and hydration of 1-butene do not proceed through a common carbocation intermediate
    • Dietze, P.E.; Jencks, W.P. Oxygen exchange into 2-butanol and hydration of 1-butene do not proceed through a common carbocation intermediate. J. Am. Chem. Soc. 1987, 109, 2057-2062.
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 2057-2062
    • Dietze, P.E.1    Jencks, W.P.2
  • 10
    • 0001702546 scopus 로고
    • Oxygen scrambling and stereochemistry during the trifluoroethanolysis of optically active 2-butyl 4-bromobenzenesulfonate
    • Dietze, P.E.; Wojciechowski, M. Oxygen scrambling and stereochemistry during the trifluoroethanolysis of optically active 2-butyl 4-bromobenzenesulfonate. J. Am. Chem. Soc. 1990, 112, 5240-5244.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 5240-5244
    • Dietze, P.E.1    Wojciechowski, M.2
  • 11
    • 0003922511 scopus 로고    scopus 로고
    • 3rd ed.; Prentice Hall: Upper Saddle River, NJ, USA
    • Bruice, P.Y. Organic Chemistry, 3rd ed.; Prentice Hall: Upper Saddle River, NJ, USA, 2001; pp. 380-381.
    • (2001) Organic Chemistry , pp. 380-381
    • Bruice, P.Y.1
  • 13
    • 63749099022 scopus 로고    scopus 로고
    • N1 involvement in the solvolysis of secondary alkyl compounds
    • Murphy, T.J. Absence of SN1 involvement in the solvolysis of secondary alkyl compounds. J. Chem. Educ. 2009, 86, 519-524.
    • (2009) J. Chem. Educ , vol.86 , pp. 519-524
    • Murphy, T.J.1
  • 14
    • 0000551025 scopus 로고
    • N1 spectrum. 1. Role of nucleophilic solvent assistance and nucleophilically solvated ion pair intermediates in solvolyses of primary and secondary arenesulfonates
    • Bentley, T.W.; Schleyer, P.V.R. The SN2-SN1 spectrum. 1. Role of nucleophilic solvent assistance and nucleophilically solvated ion pair intermediates in solvolyses of primary and secondary arenesulfonates. J. Am. Chem. Soc. 1976, 98, 7658-7666.
    • (1976) J. Am. Chem. Soc , vol.98 , pp. 7658-7666
    • Bentley, T.W.1    Schleyer, P.V.R.2
  • 15
    • 37049158697 scopus 로고
    • Oxygen exchange and the Walden inversion in sec-butyl alcohol
    • Bunton, C.A.; Konasiewicz, A.; Llewellyn, D.R. Oxygen exchange and the Walden inversion in sec-butyl alcohol. J. Chem. Soc. 1955, 604-607.
    • (1955) J. Chem. Soc , pp. 604-607
    • Bunton, C.A.1    Konasiewicz, A.2    Llewellyn, D.R.3
  • 16
    • 37049065289 scopus 로고
    • Tracer studies on alcohols. Part II. The exchange of oxygen-18 between sec-butyl alcohol and water
    • Bunton, C.A.; Llewellyn, D. R. Tracer studies on alcohols. Part II. The exchange of oxygen-18 between sec-butyl alcohol and water. J. Chem. Soc. 1957, 3402-3407.
    • (1957) J. Chem. Soc , pp. 3402-3407
    • Bunton, C.A.1    Llewellyn, D.R.2
  • 17
    • 0037070547 scopus 로고    scopus 로고
    • Hydroxide as a general base in the saponification of ethyl acetate
    • Mata-Segreda, J.F. Hydroxide as a general base in the saponification of ethyl acetate. J. Am. Chem. Soc. 2002, 124, 2259-2262.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 2259-2262
    • Mata-Segreda, J.F.1
  • 18
    • 0033535010 scopus 로고    scopus 로고
    • The catalytic effect of water in basic hydrolysis of methyl acetate: A theoretical study
    • Haeffner, F.; Hu, C.-H.; Brinck, T.; Norin, T. The catalytic effect of water in basic hydrolysis of methyl acetate: A theoretical study. J. Mol. Struct. (Theochem.) 1999, 459, 85-93.
    • (1999) J. Mol. Struct. (Theochem.) , vol.459 , pp. 85-93
    • Haeffner, F.1    Hu, C.-H.2    Brinck, T.3    Norin, T.4
  • 19
    • 17544391536 scopus 로고    scopus 로고
    • Theoretical Study On Oxygen Exchange Accompanying Alkaline Hydrolysis of Esters and Amides
    • Theochem
    • Hori, K.; Hashitani, Y.; Kaku, Y.; Ohkubo, K. Theoretical study on oxygen exchange accompanying alkaline hydrolysis of esters and amides. J. Mol. Struct. (Theochem.) 1999, 461-462, 589-596.
    • (1999) J. Mol. Struct
    • Hori, K.1    Hashitani, Y.2    Kaku, Y.3    Ohkubo, K.4
  • 20
    • 84055197995 scopus 로고    scopus 로고
    • ON, Canada. Unpublished work
    • Cox, R.A. Scarborough, ON, Canada. Unpublished work, 2011.
    • (2011) Scarborough
    • Cox, R.A.1
  • 21
    • 0000417921 scopus 로고
    • - function for dimethyl sulfoxide-water-tetramethylammonium hydroxide
    • Dolman, D.; Stewart, R. Strongly basic systems. VIII. The H- function for dimethyl sulfoxide-water-tetramethylammonium hydroxide. Can. J. Chem. 1967, 45, 911-924.
    • (1967) Can. J. Chem , vol.45 , pp. 911-924
    • Dolman, D.1    Stewart, R.2
  • 22
    • 0001957353 scopus 로고
    • Proton transfer, acid-base catalysis, and enzymatic hydrolysis. Part 1. Elementary processes
    • Eigen, M. Proton transfer, acid-base catalysis, and enzymatic hydrolysis. Part 1. Elementary processes. Angew. Chem. Int. Ed. Engl. 1964, 3, 1-19.
    • (1964) Angew. Chem. Int. Ed. Engl , vol.3 , pp. 1-19
    • Eigen, M.1
  • 23
    • 22844455879 scopus 로고    scopus 로고
    • Hydrogen bonds with large proton polarizability and proton transfer processes in electrochemistry and biology
    • and many earlier papers
    • Zundel, G. Hydrogen bonds with large proton polarizability and proton transfer processes in electrochemistry and biology. Adv. Chem. Phys. 2000, 111, 1-217, and many earlier papers.
    • (2000) Adv. Chem. Phys , vol.111 , pp. 1-217
    • Zundel, G.1
  • 24
    • 38849208504 scopus 로고    scopus 로고
    • 2+: From buckets of water to the Schrödinger equation and back
    • Niedner-Schatteburg, G. Infrared spectroscopy and ab initio theory of isolated H5O2+: from buckets of water to the Schrödinger equation and back. Angew. Chem. Int. Ed. Engl. 2008, 47, 1008-1011.
    • (2008) Angew. Chem. Int. Ed. Engl , vol.47 , pp. 1008-1011
    • Niedner-Schatteburg, G.1
  • 25
    • 0006150488 scopus 로고
    • 2+ ion in the vibrational spectra of aqueous solutions of strong acids
    • Ann. Russ. Acad. Sci. 1975, 225, 1383-1385, and many other papers
    • Librovich, N.B.; Maiorov, V.D.; Savel'ev, V.A. The H5O2+ ion in the vibrational spectra of aqueous solutions of strong acids. Dokl. Akad. Nauk SSSR 1975, 225, 1358-1361 Ann. Russ. Acad. Sci. 1975, 225, 1383-1385, and many other papers.
    • (1975) Dokl. Akad. Nauk SSSR , vol.225 , pp. 1358-1361
    • Librovich, N.B.1    Maiorov, V.D.2    Savel'ev, V.A.3
  • 26
    • 0542359056 scopus 로고
    • Properties of concentrated acid solutions. Discuss
    • Bascombe, K.N.; Bell, R.P. Properties of concentrated acid solutions. Discuss. Faraday Soc. 1957, 24, 158-161.
    • (1957) Faraday Soc , vol.24 , pp. 158-161
    • Bascombe, K.N.1    Bell, R.P.2
  • 27
    • 3342924669 scopus 로고
    • The state of the proton in aqueous sulfuric acid
    • Robertson, E.B.; Dunford, H.B. The state of the proton in aqueous sulfuric acid. J. Am. Chem. Soc. 1964, 86, 5080-5089.
    • (1964) J. Am. Chem. Soc , vol.86 , pp. 5080-5089
    • Robertson, E.B.1    Dunford, H.B.2
  • 28
    • 77957875106 scopus 로고    scopus 로고
    • Teaching mechanisms in organic chemistry
    • Ault, A. Telling it like it is
    • Ault, A. Telling it like it is: Teaching mechanisms in organic chemistry. J. Chem. Educ. 2010, 87, 922-923.
    • (2010) J. Chem. Educ , vol.87 , pp. 922-923
  • 30
    • 79955434214 scopus 로고    scopus 로고
    • Proton transfer in concentrated aqueous hydroxide visualized using ultrafast infrared spectroscopy
    • Roberts, S.T.; Ramasesha, K.; Petersen, P.B.; Mandal, A.; Tokmakoff, A. Proton transfer in concentrated aqueous hydroxide visualized using ultrafast infrared spectroscopy. J. Phys. Chem. A 2011, 115, 3957-3972.
    • (2011) J. Phys. Chem. A , vol.115 , pp. 3957-3972
    • Roberts, S.T.1    Ramasesha, K.2    Petersen, P.B.3    Mandal, A.4    Tokmakoff, A.5
  • 31
    • 77951245193 scopus 로고    scopus 로고
    • Aqueous basic solutions: Hydroxide solvation, structural diffusion, and comparison to the hydrated proton
    • Marx, D.; Chandra, A.; Tuckerman, M.E. Aqueous basic solutions: hydroxide solvation, structural diffusion, and comparison to the hydrated proton. Chem. Rev. 2010, 110, 2174-2216.
    • (2010) Chem. Rev , vol.110 , pp. 2174-2216
    • Marx, D.1    Chandra, A.2    Tuckerman, M.E.3
  • 36
    • 84055183072 scopus 로고    scopus 로고
    • Department of Chemistry, University of California, CA, USA. Private communication
    • Stoyanov, E.S.; Reed, C.A. Department of Chemistry, University of California, CA, USA. Private communication, 2011.
    • (2011)
    • Stoyanov, E.S.1    Reed, C.A.2
  • 37
    • 33744954578 scopus 로고    scopus 로고
    • n under conditions of thermal fluctuation. II. Work of formation and structure
    • Russ. J. Gen. Chem. 2004, 74, 1471-1477
    • +(H2O)n under conditions of thermal fluctuation. II. Work of formation and structure. Zh. Obshch. Khim. 2004, 74, 1585-1592; Russ. J. Gen. Chem. 2004, 74, 1471-1477.
    • (2004) Zh. Obshch. Khim , vol.74 , pp. 1585-1592
    • Shevkunov, S.V.1
  • 38
    • 0002036605 scopus 로고    scopus 로고
    • Sur la décomposition de l'eau et des corps qu'elle tient en dissolution à l'aide de l'électricité galvanique
    • Grotthuss, C.J.T. Sur la décomposition de l'eau et des corps qu'elle tient en dissolution à l'aide de l'électricité galvanique. Ann. Chim. 1806, LVIII, 54-74.
    • Ann. Chim , vol.LVIII , pp. 54-74
    • Grotthuss, C.J.T.1
  • 39
    • 65349131484 scopus 로고    scopus 로고
    • Effect of ions on the structure of water: Structure making and breakin
    • and references therein
    • Marcus, Y. Effect of ions on the structure of water: structure making and breaking. Chem. Rev. 2009, 109, 1346-1370 and references therein.
    • (2009) Chem. Rev , vol.109 , pp. 1346-1370
    • Marcus, Y.1
  • 40
    • 84855446436 scopus 로고    scopus 로고
    • 2+ and related species at higher concentrations. Aqueous HF is not often used; it is very weak at high dilution, and if concentrated it can dissolve glassware. Trifluoromethanesulfonic acid would probably be useful, but it is very expensive. Methanesulfonic acid is not used much. Trifluoroacetic and the other carboxylic acid variants are too weak to be useful
    • Aqueous HCl is only usable up to about 38 wt%, when the water is saturated with gaseous HCl, and aqueous perchloric acid only up to 78 wt% or so, when the solution solidifies at 25 °C. Nitric acid has problems and is not normally used; it is considerably weaker, it is an oxidizing agent, as is strong perchloric acid, and it can give NO2+ and related species at higher concentrations. Aqueous HF is not often used; it is very weak at high dilution, and if concentrated it can dissolve glassware. Trifluoromethanesulfonic acid would probably be useful, but it is very expensive. Methanesulfonic acid is not used much. Trifluoroacetic and the other carboxylic acid variants are too weak to be useful.
  • 41
    • 0041289143 scopus 로고
    • Mechanistic studies in strong acids. I. General considerations. Catalysis by individual acid species in sulfuric acid
    • Cox, R.A. Mechanistic studies in strong acids. I. General considerations. Catalysis by individual acid species in sulfuric acid. J. Am. Chem. Soc. 1974, 96, 1059-1063.
    • (1974) J. Am. Chem. Soc , vol.96 , pp. 1059-1063
    • Cox, R.A.1
  • 42
    • 0043235927 scopus 로고    scopus 로고
    • An ab initio molecular orbital study of the geometry of the dicationic Wallach rearrangement intermediate
    • Cox, R.A.; Fung, D.Y.K.; Csizmadia, I.G.; Buncel, E. An ab initio molecular orbital study of the geometry of the dicationic Wallach rearrangement intermediate. Can. J. Chem. 2003, 81, 535-541.
    • (2003) Can. J. Chem , vol.81 , pp. 535-541
    • Cox, R.A.1    Fung, D.Y.K.2    Csizmadia, I.G.3    Buncel, E.4
  • 43
    • 69149100069 scopus 로고    scopus 로고
    • 4 region-the Wallach rearrangement story comes full circle
    • Buncel, E.; Keum, S.-R.; Rajagopal, S.; Cox, R.A. Rearrangement mechanisms for azoxypyridines and axoxypyridine N-oxides in the 100% H2SO4 region-the Wallach rearrangement story comes full circle. Can. J. Chem. 2009, 87, 1127-1134.
    • (2009) Can. J. Chem , vol.87 , pp. 1127-1134
    • Buncel, E.1    Keum, S.-R.2    Rajagopal, S.3    Cox, R.A.4
  • 44
    • 0006929539 scopus 로고
    • Rearrangements of Hydrazo, Azoxy and Azo Compounds
    • Azo and Azoxy Groups; Patai, S.Ed.; Wiley: London, UK
    • Cox, R.A.; Buncel, E. Rearrangements of Hydrazo, Azoxy and Azo Compounds. In The Chemistry of the Hydrazo, Azo and Azoxy Groups; Patai, S., Ed.; Wiley: London, UK, 1975; Volume 1, pp. 775-859.
    • (1975) The Chemistry of the Hydrazo , vol.1 , pp. 775-859
    • Cox, R.A.1    Buncel, E.2
  • 45
    • 0042290855 scopus 로고    scopus 로고
    • Rearrangements of Hydrazo, Azoxy and Azo Compounds: Kinetic, Product and Isotope Studies
    • Patai, S., Ed.; Wiley: London, UK,
    • Cox, R.A.; Buncel, E. Rearrangements of Hydrazo, Azoxy and Azo Compounds: Kinetic, Product and Isotope Studies. In The Chemistry of the Hydrazo, Azo and Azoxy Groups; Patai, S., Ed.; Wiley: London, UK, 1997; Volume 2, pp. 569-602.
    • (1997) The Chemistry of the Hydrazo, Azo and Azoxy Groups , vol.2 , pp. 569-602
    • Cox, R.A.1    Buncel, E.2
  • 46
    • 84055188879 scopus 로고
    • Department of Chemistry, Queen's University, Kingston, Canada. Unpublished observations
    • Cox, R.A.; Buncel, E.; Bolduc, R. Department of Chemistry, Queen's University, Kingston, Canada. Unpublished observations, 1971.
    • (1971)
    • Cox, R.A.1    Buncel, E.2    Bolduc, R.3
  • 47
    • 0012200008 scopus 로고
    • Mechanistic studies in strong acids. VIII. Hydrolysis mechanisms for some thiobenzoic acids and esters in aqueous sulfuric acid, determined using the excess acidity method
    • Cox, R.A.; Yates, K. Mechanistic studies in strong acids. VIII. Hydrolysis mechanisms for some thiobenzoic acids and esters in aqueous sulfuric acid, determined using the excess acidity method. Can. J. Chem. 1982, 60, 3061-3070.
    • (1982) Can. J. Chem , vol.60 , pp. 3061-3070
    • Cox, R.A.1    Yates, K.2
  • 48
    • 0003158904 scopus 로고    scopus 로고
    • Excess acidities
    • Cox, R.A. Excess acidities. Adv. Phys. Org. Chem. 2000, 35, 1-66.
    • (2000) Adv. Phys. Org. Chem , vol.35 , pp. 1-66
    • Cox, R.A.1
  • 49
    • 0002873304 scopus 로고
    • Kinetics of the depolymerization of trioxane in aqueous acids, and the acidic properties of aqueous hydrogen fluoride
    • Bell, R.P.; Bascombe, K.N.; McCoubrey, J.C. Kinetics of the depolymerization of trioxane in aqueous acids, and the acidic properties of aqueous hydrogen fluoride. J. Chem. Soc. 1956, 1286-1291.
    • (1956) J. Chem. Soc , pp. 1286-1291
    • Bell, R.P.1    Bascombe, K.N.2    McCoubrey, J.C.3
  • 50
    • 0002662786 scopus 로고
    • The thermodynamic properties of aqueous sulfuric acid solutions and hydrates from 15 to 300 K
    • Giauque, W.F.; Hornung, E.W.; Kunzler, J.E.; Rubin, T.R. The thermodynamic properties of aqueous sulfuric acid solutions and hydrates from 15 to 300 K. J. Am. Chem. Soc. 1960, 82, 62-70.
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 62-70
    • Giauque, W.F.1    Hornung, E.W.2    Kunzler, J.E.3    Rubin, T.R.4
  • 51
    • 0001314322 scopus 로고
    • Thermodynamic properties of the aqueous sulfuric acid system to 350 K
    • Zeleznik, F.J. Thermodynamic properties of the aqueous sulfuric acid system to 350 K. J. Phys. Chem. Ref. Data 1991, 20, 1157-1200.
    • (1991) J. Phys. Chem. Ref. Data , vol.20 , pp. 1157-1200
    • Zeleznik, F.J.1
  • 52
    • 0008331565 scopus 로고
    • The calomel and silver chloride electrodes in acid and neutral solutions. The activity coefficient of aqueous hydrochloric acid and the single potential of the deci-molal calomel electrode
    • Randall, M.; Young, L.E. The calomel and silver chloride electrodes in acid and neutral solutions. The activity coefficient of aqueous hydrochloric acid and the single potential of the deci-molal calomel electrode. J. Am. Chem. Soc. 1928, 50, 989-1004.
    • (1928) J. Am. Chem. Soc , vol.50 , pp. 989-1004
    • Randall, M.1    Young, L.E.2
  • 53
    • 0001578453 scopus 로고
    • Thermodynamics of concentrated aqueous solutions of hydrochloric acid
    • Åkerlöf, G.; Teare, J.W. Thermodynamics of concentrated aqueous solutions of hydrochloric acid. J. Am. Chem. Soc. 1937, 59, 1855-1868.
    • (1937) J. Am. Chem. Soc , vol.59 , pp. 1855-1868
    • Åkerlöf, G.1    Teare, J.W.2
  • 54
    • 0027541318 scopus 로고
    • Simultaneous correlation of activity coefficient and partial thermal properties for electrolyte solutions using a model with ion-specific parameters
    • Liu, Y.; Grén, U.; Theliander, H.; Rasmuson, A. Simultaneous correlation of activity coefficient and partial thermal properties for electrolyte solutions using a model with ion-specific parameters. Fluid Phase Equilibria 1993, 83, 243-251.
    • (1993) Fluid Phase Equilibria , vol.83 , pp. 243-251
    • Liu, Y.1    Grén, U.2    Theliander, H.3    Rasmuson, A.4
  • 55
    • 0004505146 scopus 로고
    • The vapor pressures and activity coefficients of aqueous solutions of perchloric acid at 25°
    • Pearce, J.N.; Nelson, A.F. The vapor pressures and activity coefficients of aqueous solutions of perchloric acid at 25°. J. Am. Chem. Soc. 1933, 55, 3075-3081.
    • (1933) J. Am. Chem. Soc , vol.55 , pp. 3075-3081
    • Pearce, J.N.1    Nelson, A.F.2
  • 56
    • 0004481130 scopus 로고
    • The vapor pressures of perchloric acid solutions at 25°
    • Robinson, R.A.; Baker, O.J. The vapor pressures of perchloric acid solutions at 25°. Trans. Proc. R. Soc. N. Z. 1946, 76, 250-254.
    • (1946) Trans. Proc. R. Soc. N. Z , vol.76 , pp. 250-254
    • Robinson, R.A.1    Baker, O.J.2
  • 57
    • 0004513909 scopus 로고
    • Determination of the activity of water in highly concentrated perchloric acid solutions
    • Wai, H.; Yates, K. Determination of the activity of water in highly concentrated perchloric acid solutions. Can. J. Chem. 1969, 47, 2326-2328.
    • (1969) Can. J. Chem , vol.47 , pp. 2326-2328
    • Wai, H.1    Yates, K.2
  • 58
    • 0040408451 scopus 로고
    • A redetermination of the relative enthalpies of aqueous perchloric acid solutions from 1 to 24 molal
    • Bidinosti, D.R.; Biermann, W.J. A redetermination of the relative enthalpies of aqueous perchloric acid solutions from 1 to 24 molal. Can. J. Chem. 1956, 34, 1591-1595.
    • (1956) Can. J. Chem , vol.34 , pp. 1591-1595
    • Bidinosti, D.R.1    Biermann, W.J.2
  • 59
    • 0040666207 scopus 로고
    • Kinetics of the depolymerization of paraldehyde in aqueous solution
    • Bell, R.P.; Brown, A.H. Kinetics of the depolymerization of paraldehyde in aqueous solution. J. Chem. Soc. 1954, 774-778.
    • (1954) J. Chem. Soc , pp. 774-778
    • Bell, R.P.1    Brown, A.H.2
  • 60
    • 37049050184 scopus 로고
    • The Hammett acidity function in reactions catalyzed by carboxylic acids. The hydrolysis of methylal and the depolymerization of trioxane
    • Hamer, D.; Leslie, J. The Hammett acidity function in reactions catalyzed by carboxylic acids. The hydrolysis of methylal and the depolymerization of trioxane. J. Chem. Soc. 1960, 4198-4202.
    • (1960) J. Chem. Soc , pp. 4198-4202
    • Hamer, D.1    Leslie, J.2
  • 61
    • 37049062103 scopus 로고
    • Acid-catalysed ether fission. Part II. Diethyl ether in aqueous acids
    • Jaques, D.; Leisten, J.A. Acid-catalysed ether fission. Part II. Diethyl ether in aqueous acids. J. Chem. Soc. 1964, 2683-2689.
    • (1964) J. Chem. Soc , pp. 2683-2689
    • Jaques, D.1    Leisten, J.A.2
  • 62
    • 77951872219 scopus 로고    scopus 로고
    • Computational simulation of the lifetime of methoxymethyl cation in water. A simple model for a glycosyl cation: When is an intermediate an intermediate
    • Ruiz Pernía, J.J.; Tuñón, I.; Williams, I.H. Computational simulation of the lifetime of methoxymethyl cation in water. A simple model for a glycosyl cation: When is an intermediate an intermediate? J. Phys. Chem. B 2010, 114, 5769-5774.
    • (2010) J. Phys. Chem. B , vol.114 , pp. 5769-5774
    • Ruiz, P.J.J.1    Tuñón, I.2    Williams, I.H.3
  • 63
    • 42149172597 scopus 로고    scopus 로고
    • Benzamide hydrolysis in strong acids-the last word
    • Cox, R.A. Benzamide hydrolysis in strong acids-the last word. Can. J. Chem. 2008, 86, 290-297.
    • (2008) Can. J. Chem , vol.86 , pp. 290-297
    • Cox, R.A.1
  • 64
    • 33644601344 scopus 로고    scopus 로고
    • A comparison of the mechanism of hydrolysis of benzimidates, esters, and amides in sulfuric acid media
    • Cox, R.A. A comparison of the mechanism of hydrolysis of benzimidates, esters, and amides in sulfuric acid media. Can. J. Chem. 2005, 83, 1391-1399.
    • (2005) Can. J. Chem , vol.83 , pp. 1391-1399
    • Cox, R.A.1
  • 65
    • 0001443423 scopus 로고
    • Oxygen exchange as evidence for the existence of an intermediate in ester hydrolysis
    • Bender, M.L. Oxygen exchange as evidence for the existence of an intermediate in ester hydrolysis. J. Am. Chem. Soc. 1951, 73, 1626-1629.
    • (1951) J. Am. Chem. Soc , vol.73 , pp. 1626-1629
    • Bender, M.L.1
  • 66
    • 0345935575 scopus 로고
    • Benzamide oxygen exchange concurrent with acid hydrolysis
    • McClelland, R.A. Benzamide oxygen exchange concurrent with acid hydrolysis. J. Am. Chem. Soc. 1975, 97, 5281.
    • (1975) J. Am. Chem. Soc , vol.97 , pp. 5281
    • McClelland, R.A.1
  • 67
    • 0000742887 scopus 로고
    • Mechanisms of ester hydrolysis in aqueous sulfuric acids
    • Yates, K.; McClelland, R.A. Mechanisms of ester hydrolysis in aqueous sulfuric acids. J. Am. Chem. Soc. 1967, 89, 2686-2692.
    • (1967) J. Am. Chem. Soc , vol.89 , pp. 2686-2692
    • Yates, K.1    McClelland, R.A.2
  • 68
    • 33947292820 scopus 로고
    • Kinetics of ester hydrolysis in concentrated acid
    • Yates, K. Kinetics of ester hydrolysis in concentrated acid. Acc. Chem. Res. 1971, 4, 136-144.
    • (1971) Acc. Chem. Res , vol.4 , pp. 136-144
    • Yates, K.1
  • 69
    • 0001312745 scopus 로고
    • Heavy-atom isotope effects on the alkaline hydrolysis of methyl formate. The role of hydroxide ion in ester hydrolysis
    • Marlier, J.F. Heavy-atom isotope effects on the alkaline hydrolysis of methyl formate. The role of hydroxide ion in ester hydrolysis. J. Am. Chem. Soc. 1993, 115, 5953-5956.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 5953-5956
    • Marlier, J.F.1
  • 70
    • 0001186521 scopus 로고
    • Activation energies of the hydrolysis of esters and amides involving carbonyl oxygen exchange
    • Bender, M.L.; Ginger, R.D.; Unik, J.P. Activation energies of the hydrolysis of esters and amides involving carbonyl oxygen exchange. J. Am. Chem. Soc. 1958, 80, 1044-1048.
    • (1958) J. Am. Chem. Soc , vol.80 , pp. 1044-1048
    • Bender, M.L.1    Ginger, R.D.2    Unik, J.P.3
  • 71
    • 0000186855 scopus 로고
    • Absence of carbonyl oxygen exchange concurrent with the alkaline hydrolysis of substituted methyl benzoates
    • Shain, S.A.; Kirsch, J.F. Absence of carbonyl oxygen exchange concurrent with the alkaline hydrolysis of substituted methyl benzoates. J. Am. Chem. Soc. 1968, 90, 5848-5854.
    • (1968) J. Am. Chem. Soc , vol.90 , pp. 5848-5854
    • Shain, S.A.1    Kirsch, J.F.2
  • 72
    • 0031213957 scopus 로고    scopus 로고
    • The mechanism of the hydrolysis of acylimidazoles in aqueous mineral acids. The excess acidity method for reactions that are not acid catalyzed
    • Cox, R.A. The mechanism of the hydrolysis of acylimidazoles in aqueous mineral acids. The excess acidity method for reactions that are not acid catalyzed. Can. J. Chem. 1997, 75, 1093-1098.
    • (1997) Can. J. Chem , vol.75 , pp. 1093-1098
    • Cox, R.A.1
  • 73
    • 0030261898 scopus 로고    scopus 로고
    • The acid catalyzed decomposition of nitramide
    • Cox, R.A. The acid catalyzed decomposition of nitramide. Can. J. Chem. 1996, 74, 1779-1783.
    • (1996) Can. J. Chem , vol.74 , pp. 1779-1783
    • Cox, R.A.1
  • 74
    • 0034740465 scopus 로고    scopus 로고
    • Acidic and basic properties of nitramide, and the catalyzed decomposition of nitramide and related compounds; an ab initio theoretical investigation
    • Eckert-Maksic, M.; Maskill, H.; Zrinski, I. Acidic and basic properties of nitramide, and the catalyzed decomposition of nitramide and related compounds; an ab initio theoretical investigation. J. Chem. Soc. Perkin Trans. 2001, 2, 2147-2154.
    • (2001) J. Chem. Soc. Perkin Trans , vol.2 , pp. 2147-2154
    • Eckert-Maksic, M.1    Maskill, H.2    Zrinski, I.3
  • 75
    • 37049076330 scopus 로고
    • Solvolyses of para-substituted benzoyl chlorides in trifluoroethanol and in highly aqueous media
    • Bentley, T.W.; Harris, H.C. Solvolyses of para-substituted benzoyl chlorides in trifluoroethanol and in highly aqueous media. J. Chem. Soc. Perkin Trans. 1986, 2, 619-624.
    • (1986) J. Chem. Soc. Perkin Trans , vol.2 , pp. 619-624
    • Bentley, T.W.1    Harris, H.C.2
  • 76
    • 0000379649 scopus 로고
    • Concerted mechanisms of acyl group transfer reactions in solution
    • Williams, A. Concerted mechanisms of acyl group transfer reactions in solution. Acc. Chem. Res. 1989, 22, 387-392.
    • (1989) Acc. Chem. Res , vol.22 , pp. 387-392
    • Williams, A.1
  • 77
    • 14544272762 scopus 로고    scopus 로고
    • Solvent polarity and organic reactivity in mixed solvents: Evidence using a reactive molecular probe to assess the role of preferential solvation in aqueous alcohols
    • Bentley, T.W.; Ebdon, D.N.; Kim, E.-J.; Koo, I.S. Solvent polarity and organic reactivity in mixed solvents: Evidence using a reactive molecular probe to assess the role of preferential solvation in aqueous alcohols. J. Org. Chem. 2005, 70, 1647-1653.
    • (2005) J. Org. Chem , vol.70 , pp. 1647-1653
    • Bentley, T.W.1    Ebdon, D.N.2    Kim, E.-J.3    Koo, I.S.4
  • 78
    • 79958195858 scopus 로고    scopus 로고
    • N2 mechanism for the hydrolysis of acid chlorides: Comparisons of reactivities calculated by the density functional theory with experimental data
    • Ruff, F.; Farkas, Ö. Concerted SN2 mechanism for the hydrolysis of acid chlorides: comparisons of reactivities calculated by the density functional theory with experimental data. J. Phys. Org. Chem. 2011, 24, 480-491.
    • (2011) J. Phys. Org. Chem , vol.24 , pp. 480-491
    • Ruff, F.1    Farkas, O.2
  • 79
    • 79952152630 scopus 로고    scopus 로고
    • Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions
    • Ji, P.; Atherton, J.; Page, M.I. Liquid ammonia as a dipolar aprotic solvent for aliphatic nucleophilic substitution reactions. J. Org. Chem. 2011, 76, 1425-1435.
    • (2011) J. Org. Chem , vol.76 , pp. 1425-1435
    • Ji, P.1    Atherton, J.2    Page, M.I.3
  • 80
    • 79955567065 scopus 로고    scopus 로고
    • The kinetics and mechanisms of aromatic nuclear substitution reactions in liquid ammonia
    • Ji, P.; Atherton, J.H.; Page, M.I. The kinetics and mechanisms of aromatic nuclear substitution reactions in liquid ammonia. J. Org. Chem. 2011, 76, 3286-3295.
    • (2011) J. Org. Chem , vol.76 , pp. 3286-3295
    • Ji, P.1    Atherton, J.H.2    Page, M.I.3


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