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Volumn 9, Issue 11, 2008, Pages 2231-2242

Extended Grunwald-Winstein analysis - LFER used to gauge solvent effects in p-nitrophenyl chloroformate solvolysis

Author keywords

Addition elimination; Association dissociation; Chloroformates; Grunwald Winstein equation; Leaving group effects; LFERS; p nitrophenyl chloroformate; Solvolysis

Indexed keywords

FORMIC ACID DERIVATIVE;

EID: 56449113181     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms9112231     Document Type: Article
Times cited : (12)

References (47)
  • 1
    • 0000183370 scopus 로고
    • Kinetics of the Hydrolysis of Acyl Chlorides in Pure Water
    • Queen, A. Kinetics of the Hydrolysis of Acyl Chlorides in Pure Water. Can. J. Chem. 1967, 45, 1619-1629.
    • (1967) Can. J. Chem , vol.45 , pp. 1619-1629
    • Queen, A.1
  • 2
    • 0000870401 scopus 로고
    • The Kinetics of the Solvolysis of Acid Chlorides
    • Kivinen, A. The Kinetics of the Solvolysis of Acid Chlorides. Acta Chem. Scand. 1965, 19, 845-870.
    • (1965) Acta Chem. Scand , vol.19 , pp. 845-870
    • Kivinen, A.1
  • 3
    • 0000229114 scopus 로고    scopus 로고
    • SN2 Mechanism for Alcoholysis, Aminolysis, and Hydrolysis of Acetyl Chloride
    • Bentley, T.W.; Llewellyn, G.; McAlister, J.A. SN2 Mechanism for Alcoholysis, Aminolysis, and Hydrolysis of Acetyl Chloride. J. Org. Chem. 1996, 61, 7927-7932.
    • (1996) J. Org. Chem , vol.61 , pp. 7927-7932
    • Bentley, T.W.1    Llewellyn, G.2    McAlister, J.A.3
  • 4
    • 0348224196 scopus 로고    scopus 로고
    • Applications of Third Order Models in Solvolytic Reaction of Aliphatic Substituted Acyl Derivatives in 2,2,2-Trifluoroethanol-Ethanol Systems
    • Ryu, Z.H.; Lim, G.T.; Bentley, T.W. Applications of Third Order Models in Solvolytic Reaction of Aliphatic Substituted Acyl Derivatives in 2,2,2-Trifluoroethanol-Ethanol Systems. Bull. Kor. Chem. Soc. 2003, 24, 1293-1302.
    • (2003) Bull. Kor. Chem. Soc , vol.24 , pp. 1293-1302
    • Ryu, Z.H.1    Lim, G.T.2    Bentley, T.W.3
  • 6
  • 9
    • 50149086519 scopus 로고    scopus 로고
    • Structural Effects on the Solvolytic Reactivity of Carboxylic and Sulfonic Acid Chlorides. Comparisons with Gas-Phase Data for Cation Formation
    • Bentley, T.W. Structural Effects on the Solvolytic Reactivity of Carboxylic and Sulfonic Acid Chlorides. Comparisons with Gas-Phase Data for Cation Formation. J. Org. Chem. 2008, 73, 6251-6257.
    • (2008) J. Org. Chem , vol.73 , pp. 6251-6257
    • Bentley, T.W.1
  • 10
    • 0030270003 scopus 로고    scopus 로고
    • Mikulec, L.J.; Puleo, D.A. Use of p-Nitrophenyl Chloroformate Chemistry to Immobilize Protein on Orthopedic Biomaterials. J. Biomed. Mater. Res. 1996, 32, 203-208.
    • Mikulec, L.J.; Puleo, D.A. Use of p-Nitrophenyl Chloroformate Chemistry to Immobilize Protein on Orthopedic Biomaterials. J. Biomed. Mater. Res. 1996, 32, 203-208.
  • 11
    • 33947441989 scopus 로고
    • The Correlation of Solvolysis Rates
    • Grunwald, E.; Winstein, S. The Correlation of Solvolysis Rates. J. Am. Chem. Soc. 1948, 70, 846-854.
    • (1948) J. Am. Chem. Soc , vol.70 , pp. 846-854
    • Grunwald, E.1    Winstein, S.2
  • 13
    • 33947456072 scopus 로고    scopus 로고
    • Winstein, S.; Grunwald, E.; Jones, H.W. The Correlation of Solvolyses Rates and the Classification of Solvolysis Reactions into Mechanistic Categories. J. Am. Chem. Soc. 1951, 73, 2700-2707.
    • Winstein, S.; Grunwald, E.; Jones, H.W. The Correlation of Solvolyses Rates and the Classification of Solvolysis Reactions into Mechanistic Categories. J. Am. Chem. Soc. 1951, 73, 2700-2707.
  • 14
    • 33847797449 scopus 로고
    • The SN2-SN1 Spectrum. 2. Quantitative Treatments of Nucleophilic Solvent Assistance. A Scale of Solvent Nucleophilicities
    • Schadt, F.L.; Bentley, T.W.; Schleyer, P.v.R. The SN2-SN1 Spectrum. 2. Quantitative Treatments of Nucleophilic Solvent Assistance. A Scale of Solvent Nucleophilicities. J. Am. Chem. Soc. 1976, 98, 7667-7674.
    • (1976) J. Am. Chem. Soc , vol.98 , pp. 7667-7674
    • Schadt, F.L.1    Bentley, T.W.2    Schleyer, P.V.R.3
  • 15
    • 0000862017 scopus 로고
    • An Improved Scale of Solvent Nucleophilicity Based on the Solvolysis of the S-Methyldibenzothiophenium Ion
    • Kevill, D.N.; Anderson, S.W. An Improved Scale of Solvent Nucleophilicity Based on the Solvolysis of the S-Methyldibenzothiophenium Ion. J. Org. Chem. 1991, 56, 1845-1850.
    • (1991) J. Org. Chem , vol.56 , pp. 1845-1850
    • Kevill, D.N.1    Anderson, S.W.2
  • 16
    • 0002732089 scopus 로고    scopus 로고
    • Development and Uses of Scales of Solvent Nucleophilicity
    • Charton, M, Ed, JAI Press: Greenwich, CT
    • Kevill, D.N. Development and Uses of Scales of Solvent Nucleophilicity. In Advances in Quantitative Structure-Property Relationships; Charton, M., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 1, pp. 81-115.
    • (1996) Advances in Quantitative Structure-Property Relationships , vol.1 , pp. 81-115
    • Kevill, D.N.1
  • 18
    • 33747144106 scopus 로고    scopus 로고
    • Correlations and Predictions of Solvent Effects on Reactivity: Some Limitations of Multi-Parameter Equations and Comparisons with Similarity Models Based on One Solvent Parameter
    • Bentley, T.W.; Garley, M.S. Correlations and Predictions of Solvent Effects on Reactivity: Some Limitations of Multi-Parameter Equations and Comparisons with Similarity Models Based on One Solvent Parameter. J. Phys. Org. Chem. 2006, 19, 341-349.
    • (2006) J. Phys. Org. Chem , vol.19 , pp. 341-349
    • Bentley, T.W.1    Garley, M.S.2
  • 19
    • 44649161083 scopus 로고    scopus 로고
    • Sixty Years of the Grunwald-Winstein Equation: Development and Recent Applications
    • Kevill, D.N.; D'Souza, M.J. Sixty Years of the Grunwald-Winstein Equation: Development and Recent Applications. J. Chem. Res. 2008, 61-66.
    • (2008) J. Chem. Res , pp. 61-66
    • Kevill, D.N.1    D'Souza, M.J.2
  • 20
    • 33751554171 scopus 로고
    • Solvolysis-Decomposition of 1-Adamantyl Chloroformate: Evidence for Ion Pair Return in 1-Adamantyl Chloride Solvolysis
    • Kevill, D.N.; Kyong, J.B.; Weitl, F.L. Solvolysis-Decomposition of 1-Adamantyl Chloroformate: Evidence for Ion Pair Return in 1-Adamantyl Chloride Solvolysis. J. Org. Chem. 1990, 55, 4304-4311.
    • (1990) J. Org. Chem , vol.55 , pp. 4304-4311
    • Kevill, D.N.1    Kyong, J.B.2    Weitl, F.L.3
  • 21
    • 0005051532 scopus 로고    scopus 로고
    • Stoichiometric Solvation Effects. Product-Rate Correlation for the Solvolyses of Phenyl Chloroformate in Alcohol-Water Mixtures
    • Koo, I.S.; Yang, K.; Kang, K.; Oh, H.K.; Lee, I. Stoichiometric Solvation Effects. Product-Rate Correlation for the Solvolyses of Phenyl Chloroformate in Alcohol-Water Mixtures. Bull. Korean Chem. Soc. 1996, 17, 520-524.
    • (1996) Bull. Korean Chem. Soc , vol.17 , pp. 520-524
    • Koo, I.S.1    Yang, K.2    Kang, K.3    Oh, H.K.4    Lee, I.5
  • 22
    • 0001074192 scopus 로고    scopus 로고
    • Concerning the Two Reaction Channels for the Solvolyses of Ethyl Chloroformate and Ethyl Chlorothioformate
    • Kevill, D.N.; D'Souza, M.J. Concerning the Two Reaction Channels for the Solvolyses of Ethyl Chloroformate and Ethyl Chlorothioformate. J. Org. Chem. 1998, 63, 2120-2124.
    • (1998) J. Org. Chem , vol.63 , pp. 2120-2124
    • Kevill, D.N.1    D'Souza, M.J.2
  • 23
    • 0344417017 scopus 로고    scopus 로고
    • Correlation of the Rates of Methyl Chloroformate with Solvent Properties
    • Kevill, D.N.; Kim, J.C.; Kyong, J.B. Correlation of the Rates of Methyl Chloroformate with Solvent Properties. J. Chem. Res. Synop. 1999, 150-151.
    • (1999) J. Chem. Res. Synop , pp. 150-151
    • Kevill, D.N.1    Kim, J.C.2    Kyong, J.B.3
  • 24
  • 25
    • 0036007773 scopus 로고    scopus 로고
    • Correlation of the Rates of Solvolyses of n-Octyl Fluoroformate and a Comparison with n-Octyl Chloroformate Solvolyses
    • Kevill, D.N.; D'Souza, M.J. Correlation of the Rates of Solvolyses of n-Octyl Fluoroformate and a Comparison with n-Octyl Chloroformate Solvolyses. J. Chem. Soc., Perkin Trans. 2 2002, 240-243.
    • (2002) J. Chem. Soc., Perkin Trans. 2 , pp. 240-243
    • Kevill, D.N.1    D'Souza, M.J.2
  • 26
    • 0037414520 scopus 로고    scopus 로고
    • Solvolysis-Decomposition of 2-Adamantyl Chloroformate: Evidence for Two Reaction Pathways
    • Kyong, J.B.; Yoo, J.-S.; Kevill, D.N. Solvolysis-Decomposition of 2-Adamantyl Chloroformate: Evidence for Two Reaction Pathways. J. Org. Chem. 2003, 68, 3425-3432
    • (2003) J. Org. Chem , vol.68 , pp. 3425-3432
    • Kyong, J.B.1    Yoo, J.-S.2    Kevill, D.N.3
  • 27
    • 14644406279 scopus 로고    scopus 로고
    • Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Chloroformate
    • Kyong, J.B.; Won, H.; Kevill, D.N. Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Chloroformate. Int. J. Mol. Sci. 2005, 6, 87-96.
    • (2005) Int. J. Mol. Sci , vol.6 , pp. 87-96
    • Kyong, J.B.1    Won, H.2    Kevill, D.N.3
  • 28
    • 27444447650 scopus 로고    scopus 로고
    • Mechanisms of Solvolyses of Acid Chlorides and Chloroformates. Chloroacetyl and Phenylacetyl Chloride as Similarity Models
    • Bentley, T.W.; Harris, H.C.; Zoon H.-R.; Gui, T.L.; Dae, D.S.; Szajda, S.R. Mechanisms of Solvolyses of Acid Chlorides and Chloroformates. Chloroacetyl and Phenylacetyl Chloride as Similarity Models. J. Org. Chem. 2005, 70, 8963-8970.
    • (2005) J. Org. Chem , vol.70 , pp. 8963-8970
    • Bentley, T.W.1    Harris, H.C.2    Zoon, H.-R.3    Gui, T.L.4    Dae, D.S.5    Szajda, S.R.6
  • 29
    • 31744443777 scopus 로고    scopus 로고
    • Stoichiometric Effects. Correlation of the Rates of Solvolysis of Isopropenyl Chloroformate
    • Ryu, Z.H.; Lee, Y.H.; Oh, Y. Stoichiometric Effects. Correlation of the Rates of Solvolysis of Isopropenyl Chloroformate. Bull. Kor. Chem. Soc. 2005, 26, 1761-1766.
    • (2005) Bull. Kor. Chem. Soc , vol.26 , pp. 1761-1766
    • Ryu, Z.H.1    Lee, Y.H.2    Oh, Y.3
  • 30
    • 0001201304 scopus 로고    scopus 로고
    • Correlation of the Rates of Solvolysis of Phenyl Chloroformate
    • Kevill, D.N.; D'Souza, M.J. Correlation of the Rates of Solvolysis of Phenyl Chloroformate. J. Chem. Soc., Perkin Trans. 2 1997, 1721-1724.
    • (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 1721-1724
    • Kevill, D.N.1    D'Souza, M.J.2
  • 31
    • 0005079102 scopus 로고    scopus 로고
    • Stoichiometric Solvation Effects. Part 4. Product-rate Correlations for Solvolyses of p-Methoxyphenyl Chloroformate in Alcohol-Water Mixtures
    • Koo, I.S.; Yang, K.; Koo, J.C.; Park, J.-K.; Lee, I. Stoichiometric Solvation Effects. Part 4. Product-rate Correlations for Solvolyses of p-Methoxyphenyl Chloroformate in Alcohol-Water Mixtures. Bull. Korean Chem. Soc. 1997, 18, 1017-1021.
    • (1997) Bull. Korean Chem. Soc , vol.18 , pp. 1017-1021
    • Koo, I.S.1    Yang, K.2    Koo, J.C.3    Park, J.-K.4    Lee, I.5
  • 32
    • 0003167983 scopus 로고    scopus 로고
    • Stoichiometric Solvation Effects. Part 3. Product-rate Correlations for Solvolyses of p-Nitrophenyl Chloroformate in Alcohol-Water Mixtures
    • Koo, I.S.; Yang, K.; Kang, K.; Lee, I.; Bentley, T.W. Stoichiometric Solvation Effects. Part 3. Product-rate Correlations for Solvolyses of p-Nitrophenyl Chloroformate in Alcohol-Water Mixtures. J. Chem. Soc. Perkin Trans 2 1998, 1179-1183.
    • (1998) J. Chem. Soc. Perkin Trans 2 , pp. 1179-1183
    • Koo, I.S.1    Yang, K.2    Kang, K.3    Lee, I.4    Bentley, T.W.5
  • 33
    • 0001135948 scopus 로고    scopus 로고
    • Transition-State Variation in the Solvolyses of para-Substituted Phenyl Chloroformates in Alcohol-Water Mixtures
    • Koo, I.S.; Yang, K.; Kang, K.; Lee, I. Transition-State Variation in the Solvolyses of para-Substituted Phenyl Chloroformates in Alcohol-Water Mixtures. Bull. Kor. Chem. Soc. 1998, 19, 968-973.
    • (1998) Bull. Kor. Chem. Soc , vol.19 , pp. 968-973
    • Koo, I.S.1    Yang, K.2    Kang, K.3    Lee, I.4
  • 34
    • 0034694732 scopus 로고    scopus 로고
    • Nucleophilic Substitution Reactions of p-Nitrobenzyl Chloroformate
    • Park, K.H.; Kyong, J.B.; Kevill, D.N. Nucleophilic Substitution Reactions of p-Nitrobenzyl Chloroformate. Bull. Kor. Chem. Soc. 2000, 21, 1267-1270.
    • (2000) Bull. Kor. Chem. Soc , vol.21 , pp. 1267-1270
    • Park, K.H.1    Kyong, J.B.2    Kevill, D.N.3
  • 35
    • 0034680621 scopus 로고    scopus 로고
    • Rate and Product Studies with Benzyl and p-Nitrobenzyl Chloroformates under Solvolytic Conditions
    • Kyong, J.B.; Park, B.-C.; Kim, C.-B.; Kevill, D.N. Rate and Product Studies with Benzyl and p-Nitrobenzyl Chloroformates under Solvolytic Conditions. J. Org. Chem. 2000, 65, 8051-8058.
    • (2000) J. Org. Chem , vol.65 , pp. 8051-8058
    • Kyong, J.B.1    Park, B.-C.2    Kim, C.-B.3    Kevill, D.N.4
  • 36
    • 34248228599 scopus 로고    scopus 로고
    • Correlation of the Specific Rates of Solvolysis of Aromatic Carbamoyl Chlorides, Chloroformates, Chlorothionoformates, and Chlorodithioformates Revisited
    • Kevill, D.N.; Koyoshi, F.; D'Souza, M.J. Correlation of the Specific Rates of Solvolysis of Aromatic Carbamoyl Chlorides, Chloroformates, Chlorothionoformates, and Chlorodithioformates Revisited. Int. J. Mol. Sci. 2007, 8, 346-352.
    • (2007) Int. J. Mol. Sci , vol.8 , pp. 346-352
    • Kevill, D.N.1    Koyoshi, F.2    D'Souza, M.J.3
  • 37
    • 34548400753 scopus 로고    scopus 로고
    • Consideration of the Factors Influencing the Specific Rates of Solvolysis of p-Methoxyphenyl Chloroformate
    • D'Souza, M.J.; Reed, D.; Koyoshi, F.; Kevill, D.N. Consideration of the Factors Influencing the Specific Rates of Solvolysis of p-Methoxyphenyl Chloroformate. Int. J. Mol. Sci. 2007, 8, 788-796.
    • (2007) Int. J. Mol. Sci , vol.8 , pp. 788-796
    • D'Souza, M.J.1    Reed, D.2    Koyoshi, F.3    Kevill, D.N.4
  • 38
    • 43949088480 scopus 로고    scopus 로고
    • Correlation of the Rates of Solvolysis of Acetyl Chloride and á-Substituted Derivatives
    • D'Souza, M.J.; Ryu, Z.H.; Park, B.-C.; Kevill, D.N. Correlation of the Rates of Solvolysis of Acetyl Chloride and á-Substituted Derivatives. Can. J. Chem. 2008, 86, 359-367.
    • (2008) Can. J. Chem , vol.86 , pp. 359-367
    • D'Souza, M.J.1    Ryu, Z.H.2    Park, B.-C.3    Kevill, D.N.4
  • 39
    • 0035309124 scopus 로고    scopus 로고
    • Structure-Reactitvity Correlations in the Aminolysis of Aryl Chloroformates
    • Castro, E.A.; Ruiz, M.G.; Santos, J.G. Structure-Reactitvity Correlations in the Aminolysis of Aryl Chloroformates. Int. J. Chem. Kinet. 2001, 281-287.
    • (2001) Int. J. Chem. Kinet , pp. 281-287
    • Castro, E.A.1    Ruiz, M.G.2    Santos, J.G.3
  • 40
    • 0344562165 scopus 로고
    • Nucleophilicity and Ionizing Power in Binary Solvent Mixtures
    • Kaspi, J.; Rappoport, Z. Nucleophilicity and Ionizing Power in Binary Solvent Mixtures. Tetrahedron Lett. 1977, 2035.
    • (1977) Tetrahedron Lett , pp. 2035
    • Kaspi, J.1    Rappoport, Z.2
  • 42
    • 33947321426 scopus 로고    scopus 로고
    • Kevill, D.N.; Ryu, Z.H. Additional Solvent Ionizing Power Values for Binary Water - 1,1,1,3,3,3,-Hexafluoro-2-propanol Solvents. Int. J. Mol. Sci. 2006, 7, 451-455.
    • Kevill, D.N.; Ryu, Z.H. Additional Solvent Ionizing Power Values for Binary Water - 1,1,1,3,3,3,-Hexafluoro-2-propanol Solvents. Int. J. Mol. Sci. 2006, 7, 451-455.
  • 43
    • 33845553885 scopus 로고    scopus 로고
    • Bentley, T.W.; Carter, G.E. The SN2-SN1 Spectrum. 4. Mechanism for Solvolyses of tert-Butyl Chloride: A Revised Y Scale of Solvent Ionizing Power based on Solvolyses of 1-Adamantyl Chloride. J. Am. Chem. Soc. 1982, 104, 5741-5747.
    • Bentley, T.W.; Carter, G.E. The SN2-SN1 Spectrum. 4. Mechanism for Solvolyses of tert-Butyl Chloride: A Revised Y Scale of Solvent Ionizing Power based on Solvolyses of 1-Adamantyl Chloride. J. Am. Chem. Soc. 1982, 104, 5741-5747.
  • 44
    • 0003104087 scopus 로고
    • Additional YCl Values and Correlation of the Specific Rates of Solvolysis of tert-Butyl Chloride in Terms of NT and YCl Scales
    • Kevill, D.N.; D'Souza, M.J. Additional YCl Values and Correlation of the Specific Rates of Solvolysis of tert-Butyl Chloride in Terms of NT and YCl Scales. J. Chem. Res. Synop. 1993, 174-175.
    • (1993) J. Chem. Res. Synop , pp. 174-175
    • Kevill, D.N.1    D'Souza, M.J.2
  • 45
  • 47
    • 0034697140 scopus 로고    scopus 로고
    • Correlation of the Rates of Solvolysis of Cyclopropylcarbinyl and Cyclobutyl Bromides Using the Extended Grunwald-Winstein Equation
    • Kevill, D.N.; Abduljaber, M.H. Correlation of the Rates of Solvolysis of Cyclopropylcarbinyl and Cyclobutyl Bromides Using the Extended Grunwald-Winstein Equation. J. Org. Chem. 2000, 65, 2548-2554.
    • (2000) J. Org. Chem , vol.65 , pp. 2548-2554
    • Kevill, D.N.1    Abduljaber, M.H.2


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