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Volumn 9, Issue 9, 2008, Pages 1704-1716

The influence of carbon-carbon multiple bonds on the solvolyses of tertiary alkyl halides: A grunwald-winstein analysis

Author keywords

Carbon carbon multiple bonds; Grunwald Winstein Equation; Solvent effects; Tertiary alkyl halides

Indexed keywords

2 BROMO 2 METHYL 1 PHENYLPROPANE; 2 CHLORO 2 METHYLBUTANE; 2 CHLORO 2 PHENYLPROPANE; 3 CHLORO 3 METHYLBUTYNE; 4 CHLORO 4 METHYL 2 PENTYNE; CARBON; HALIDE; TERTIARY ALKYL GROUP; UNCLASSIFIED DRUG;

EID: 53549099402     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms9091704     Document Type: Article
Times cited : (4)

References (35)
  • 1
    • 37049076695 scopus 로고
    • Linear solvation energy relationships. 37. An analysis of contributions of dipolarity polarizability, nucleophilic assistance, electrophilic assistance, and cavity terms to solvent effects on tert-butyl halide solvolysis rates
    • Abraham, M.H.; Doherty, R.M.; Kamlet, M.J.; Harris, J.M.; Taft, R.W. Linear solvation energy relationships. 37. An analysis of contributions of dipolarity polarizability, nucleophilic assistance, electrophilic assistance, and cavity terms to solvent effects on tert-butyl halide solvolysis rates. J. Chem. Soc. Perkin 2 1987, 913-920.
    • (1987) J. Chem. Soc. Perkin 2 , pp. 913-920
    • Abraham, M.H.1    Doherty, R.M.2    Kamlet, M.J.3    Harris, J.M.4    Taft, R.W.5
  • 2
    • 33845553885 scopus 로고
    • N2 (intermediate) mechanism for solvolyses of tert-butyl chloride-a revised Y-scale of solvent ionizing power based on solvolyses of 1-adamantyl chloride
    • N2 (intermediate) 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.
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 5741-5747
    • Bentley, T.W.1    Carter, G.E.2
  • 3
    • 8344236690 scopus 로고    scopus 로고
    • Solvation effects in the heterolyses of 3-X-3-methylpentanes (X = Cl, Br, I)
    • Martins, F.; Leitao, R.E.; Moreira, L. Solvation effects in the heterolyses of 3-X-3-methylpentanes (X = Cl, Br, I). J. Phys. Org. Chem. 2004, 17, 1061-1066.
    • (2004) J. Phys. Org. Chem , vol.17 , pp. 1061-1066
    • Martins, F.1    Leitao, R.E.2    Moreira, L.3
  • 4
    • 33947441989 scopus 로고
    • The correlation of solvolysis rates
    • Grunwald, E.; Winstein, S. The correlation of solvolysis rates. J. Am. Chem. Soc. 1948, 70, 846-859.
    • (1948) J. Am. Chem. Soc , vol.70 , pp. 846-859
    • Grunwald, E.1    Winstein, S.2
  • 5
    • 0003104087 scopus 로고
    • Additional Y(C1) values and the correlation of the specific rates of solvolysis of tert-butyl chloride in terms of N(T) and Y(C1) scales
    • KeviH, D.N.; D'Souza, M.J. Additional Y(C1) values and the correlation of the specific rates of solvolysis of tert-butyl chloride in terms of N(T) and Y(C1) scales. J. Chem. Res.-S 1993, 174-175.
    • (1993) J. Chem. Res.-S , pp. 174-175
    • KeviH, D.N.1    D'Souza, M.J.2
  • 6
    • 0000291188 scopus 로고    scopus 로고
    • Solvolytic reactions in fluorinated alcohols. Role of nucleophilic and other solvation effects
    • Bentley, T.W.; Llewellyn, G.; Ryu, Z.H. Solvolytic reactions in fluorinated alcohols. Role of nucleophilic and other solvation effects. J. Org. Chem. 1998, 63, 4654-4659.
    • (1998) J. Org. Chem , vol.63 , pp. 4654-4659
    • Bentley, T.W.1    Llewellyn, G.2    Ryu, Z.H.3
  • 7
    • 0036902705 scopus 로고    scopus 로고
    • Correlation of the rates of solvolysis of benzoyl chloride and derivatives using extended forms of the Grunwald-Winstein equation
    • Kevill, D.N.; D'Souza, M.J. Correlation of the rates of solvolysis of benzoyl chloride and derivatives using extended forms of the Grunwald-Winstein equation. J. Phys. Org. Chem. 2002, 15, 881-888.
    • (2002) J. Phys. Org. Chem , vol.15 , pp. 881-888
    • Kevill, D.N.1    D'Souza, M.J.2
  • 9
    • 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
  • 10
    • 33947456072 scopus 로고
    • The correlation of solvolysis rates and the classification of solvolysis reactions into mechanistic categories
    • Winstein, S.; Grunwald, E.; Jones, H.W. The correlation of solvolysis rates and the classification of solvolysis reactions into mechanistic categories. J. Am. Chem. Soc. 1951, 73, 2700-2707.
    • (1951) J. Am. Chem. Soc , vol.73 , pp. 2700-2707
    • Winstein, S.1    Grunwald, E.2    Jones, H.W.3
  • 11
    • 0001026937 scopus 로고
    • Correlation of solvolysis rates. 8. Benzhydryl chloride and bromide - comparison of my and Swain's correlations
    • Winstein, S.; Fainberg, A.H.; Grunwald, E. Correlation of solvolysis rates. 8. Benzhydryl chloride and bromide - comparison of my and Swain's correlations. J. Am. Chem. Soc. 1957, 79, 4146-4155.
    • (1957) J. Am. Chem. Soc , vol.79 , pp. 4146-4155
    • Winstein, S.1    Fainberg, A.H.2    Grunwald, E.3
  • 12
    • 33644610627 scopus 로고
    • Medium effects on the rates and mechanisms of solvolytic reactions
    • Bentley, T.W.; Schleyer, P.v.R. Medium effects on the rates and mechanisms of solvolytic reactions Adv. Phys. Org. Chem. 1977, 14, 1-67.
    • (1977) Adv. Phys. Org. Chem , vol.14 , pp. 1-67
    • Bentley, T.W.1    Schleyer, P.V.R.2
  • 13
    • 0001496673 scopus 로고
    • Correlation of solvolysis rates with 3-parameter and 4-parameter relationships - scale of solvent nucleophilicities
    • Bentley, T.W.; Schadt, F.L.; Schleyer, P.v.R. Correlation of solvolysis rates with 3-parameter and 4-parameter relationships - scale of solvent nucleophilicities. J. Am. Chem. Soc. 1972, 94, 992-995.
    • (1972) J. Am. Chem. Soc , vol.94 , pp. 992-995
    • Bentley, T.W.1    Schadt, F.L.2    Schleyer, P.V.R.3
  • 15
    • 37049076481 scopus 로고
    • Considerably improved Grunwald-Winstein correlations for solvolyses of several secondary and tertiary benzylic derivatives upon inclusion of a term governed by the aromatic ring parameter (I)
    • Kevill, D.N.; D'Souza, M.J. Considerably improved Grunwald-Winstein correlations for solvolyses of several secondary and tertiary benzylic derivatives upon inclusion of a term governed by the aromatic ring parameter (I). J. Chem. Soc. Perkin 2 1995, 973-980.
    • (1995) J. Chem. Soc. Perkin 2 , pp. 973-980
    • Kevill, D.N.1    D'Souza, M.J.2
  • 16
    • 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
  • 17
    • 0035823833 scopus 로고    scopus 로고
    • Is the tert-butyl chloride solvolysis the most misunderstood reaction in organic chemistry? Evidence against nucleophilic solvent participation in the tert-butyl chloride transition state and for increased hydrogen bond donation to the 1-adamantyl chloride solvolysis transition state
    • Gajewski, J.J. Is the tert-butyl chloride solvolysis the most misunderstood reaction in organic chemistry? Evidence against nucleophilic solvent participation in the tert-butyl chloride transition state and for increased hydrogen bond donation to the 1-adamantyl chloride solvolysis transition state. J. Am. Chem. Soc. 2001, 123, 10877-10883.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 10877-10883
    • Gajewski, J.J.1
  • 19
    • 0035850271 scopus 로고    scopus 로고
    • What is the stabilizing interaction with nucleophilic solvents in the transition state for solvolysis of tertiary derivatives: Nucleophilic solvent participation or nucleophilic solvation?
    • Richard, J.P.; Toteva, M.M.; Amyes, T.L. What is the stabilizing interaction with nucleophilic solvents in the transition state for solvolysis of tertiary derivatives: Nucleophilic solvent participation or nucleophilic solvation? Org. Lett. 2001, 3, 2225-2228.
    • (2001) Org. Lett , vol.3 , pp. 2225-2228
    • Richard, J.P.1    Toteva, M.M.2    Amyes, T.L.3
  • 20
    • 0001062722 scopus 로고    scopus 로고
    • B-strain and solvolytic reactivity revisited. Nucleophilic solvent participation and abnormal rate ratios for tertiary chloroalkanes
    • Liu, K.T.; Hou, S.J.; Tsao, M.L. B-strain and solvolytic reactivity revisited. Nucleophilic solvent participation and abnormal rate ratios for tertiary chloroalkanes. J. Org. Chem. 1998, 63, 1360-1362.
    • (1998) J. Org. Chem , vol.63 , pp. 1360-1362
    • Liu, K.T.1    Hou, S.J.2    Tsao, M.L.3
  • 21
    • 0001577016 scopus 로고    scopus 로고
    • Structural effects on the Grunwald-Winstein correlations in the solvolysis of some simple tertiary alkyl chlorides
    • Takeuchi, K.; Ohga, Y.; Ushino, T.; Takasuka, M. Structural effects on the Grunwald-Winstein correlations in the solvolysis of some simple tertiary alkyl chlorides. J. Phys. Org. Chem. 1997, 10, 717-724.
    • (1997) J. Phys. Org. Chem , vol.10 , pp. 717-724
    • Takeuchi, K.1    Ohga, Y.2    Ushino, T.3    Takasuka, M.4
  • 22
    • 21844502920 scopus 로고
    • Solvent effects on localized and delocalized cationic charges in solvolysis
    • Lee, I.; Koh, H.J.; Chang, B.D. Solvent effects on localized and delocalized cationic charges in solvolysis. Bull. Kor. Chem. Soc. 1995, 16, 1104-1108.
    • (1995) Bull. Kor. Chem. Soc , vol.16 , pp. 1104-1108
    • Lee, I.1    Koh, H.J.2    Chang, B.D.3
  • 23
    • 0000101046 scopus 로고
    • Solvolysis of the (p-methoxybenzyl)dimethylsulfonium ion-development and use of a scale to correct for dispersion in Grunwald-Winstein plots
    • Kevill, D.N.; Ismail, N.H.J.; D'Souza, MJ. Solvolysis of the (p-methoxybenzyl)dimethylsulfonium ion-development and use of a scale to correct for dispersion in Grunwald-Winstein plots. J. Org. Chem. 1994, 59, 6303-6312.
    • (1994) J. Org. Chem , vol.59 , pp. 6303-6312
    • Kevill, D.N.1    Ismail, N.H.J.2    D'Souza, M.J.3
  • 24
    • 0032482488 scopus 로고    scopus 로고
    • Application of the aromatic ring parameter (I) to solvolyses of extremely crowded alkyl derivatives
    • Kevill, D.N.; D'Souza, MJ. Application of the aromatic ring parameter (I) to solvolyses of extremely crowded alkyl derivatives. Tetrahedron Lett. 1998, 39, 3973-3976.
    • (1998) Tetrahedron Lett , vol.39 , pp. 3973-3976
    • Kevill, D.N.1    D'Souza, M.J.2
  • 25
    • 53549112014 scopus 로고    scopus 로고
    • Kevill, D.N.; D'Souza, MJ. Incorporation of a term governed by the aromatic ring parameter (I) into Grunwald-Winstein correlations of the solvolyses of diarylmethyl, naphthylmethyl and arylmethyl bromides. J. Chem. Res.-S 1996, 286-287 and J. Chem. Res.-M 1996, 1646-1654.
    • Kevill, D.N.; D'Souza, MJ. Incorporation of a term governed by the aromatic ring parameter (I) into Grunwald-Winstein correlations of the solvolyses of diarylmethyl, naphthylmethyl and arylmethyl bromides. J. Chem. Res.-S 1996, 286-287 and J. Chem. Res.-M 1996, 1646-1654.
  • 26
    • 0011490285 scopus 로고    scopus 로고
    • Comments on the utility of aromatic ring parameters in the correlation analysis of solvolytic reactivities for benzylic substrates
    • Liu, K.T. Comments on the utility of aromatic ring parameters in the correlation analysis of solvolytic reactivities for benzylic substrates. J. Chem. Soc. Perkin 2 1996, 327-328.
    • (1996) J. Chem. Soc. Perkin 2 , pp. 327-328
    • Liu, K.T.1
  • 27
    • 0001575578 scopus 로고
    • Solvation effects adjacent to the reaction site - differences in solvation between alkyl, alkenyl, or alkynyl and aryl groups in binary aqueous mixtures
    • Bentley, T.W.; Dauschmidt, J.P.; Llewellyn, G.; Mayr, H. Solvation effects adjacent to the reaction site - differences in solvation between alkyl, alkenyl, or alkynyl and aryl groups in binary aqueous mixtures. J. Org. Chem. 1992, 57, 2387-2392.
    • (1992) J. Org. Chem , vol.57 , pp. 2387-2392
    • Bentley, T.W.1    Dauschmidt, J.P.2    Llewellyn, G.3    Mayr, H.4
  • 28
    • 33745034258 scopus 로고    scopus 로고
    • Solvent and temperature effects on ion association and mobility of 2,6-lutidinium chloride in non-aqueous solvents
    • Moreira, L.; Leitao, R.E.; Martins, F. Solvent and temperature effects on ion association and mobility of 2,6-lutidinium chloride in non-aqueous solvents. Mol. Phys. 2006, 104, 1905-1913.
    • (2006) Mol. Phys , vol.104 , pp. 1905-1913
    • Moreira, L.1    Leitao, R.E.2    Martins, F.3
  • 30
    • 53549098669 scopus 로고    scopus 로고
    • Moreira, L.; Martins, F.; Leitao, R.E. Comparative studies of solvent effects in heterolyses of tertiary alkyl halides: the Grunwald-Winstein plots vs. enlarged TAKA equation. Communication to ESORX; Rome, 2005.
    • Moreira, L.; Martins, F.; Leitao, R.E. Comparative studies of solvent effects in heterolyses of tertiary alkyl halides: the Grunwald-Winstein plots vs. enlarged TAKA equation. Communication to ESORX; Rome, 2005.
  • 32
    • 0032360912 scopus 로고    scopus 로고
    • Solvent effects on the solvolysis of 2-aryl-1,ldimethylethyl bromides
    • Hwang, Y.H.; Kim, S.H.; Gee, J.G.; Yoh, S.D. Solvent effects on the solvolysis of 2-aryl-1,ldimethylethyl bromides. Bull. Kor. Chem. Soc. 1998, 19, 349-353.
    • (1998) Bull. Kor. Chem. Soc , vol.19 , pp. 349-353
    • Hwang, Y.H.1    Kim, S.H.2    Gee, J.G.3    Yoh, S.D.4
  • 33
    • 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
  • 34
    • 0001101096 scopus 로고
    • A convenient method for the preparation of highly pure tert-alkyl bromides and iodides
    • Masada, H.; Murotani, Y. A convenient method for the preparation of highly pure tert-alkyl bromides and iodides. Bull. Chem. Soc. Jpn 1980, 53, 1181-1182.
    • (1980) Bull. Chem. Soc. Jpn , vol.53 , pp. 1181-1182
    • Masada, H.1    Murotani, Y.2
  • 35
    • 33845276711 scopus 로고    scopus 로고
    • Design of an excel spreadsheet to estimate rate constants, determine associated errors, and choose curve's extent
    • Moreira, L.; Martins, F.; Leitao, R.E. Design of an excel spreadsheet to estimate rate constants, determine associated errors, and choose curve's extent. J. Chem. Educ. 2006, 83, 1879-1883.
    • (2006) J. Chem. Educ , vol.83 , pp. 1879-1883
    • Moreira, L.1    Martins, F.2    Leitao, R.E.3


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