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The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate

Dennis N. Kevill ; Department of Chemistry, Northern Illinois University, DeKalb, IL 60115
Mohamad H. Abduljaber ; Department of Chemistry, Northern Illinois University, DeKalb, IL 60115

Puni tekst: engleski, pdf (19 MB) str. 539-546 preuzimanja: 125* citiraj
APA 6th Edition
Kevill, D.N. i Abduljaber, M.H. (1992). The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate. Croatica Chemica Acta, 65 (3), 539-546. Preuzeto s https://hrcak.srce.hr/137114
MLA 8th Edition
Kevill, Dennis N. i Mohamad H. Abduljaber. "The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate." Croatica Chemica Acta, vol. 65, br. 3, 1992, str. 539-546. https://hrcak.srce.hr/137114. Citirano 08.03.2021.
Chicago 17th Edition
Kevill, Dennis N. i Mohamad H. Abduljaber. "The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate." Croatica Chemica Acta 65, br. 3 (1992): 539-546. https://hrcak.srce.hr/137114
Harvard
Kevill, D.N., i Abduljaber, M.H. (1992). 'The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate', Croatica Chemica Acta, 65(3), str. 539-546. Preuzeto s: https://hrcak.srce.hr/137114 (Datum pristupa: 08.03.2021.)
Vancouver
Kevill DN, Abduljaber MH. The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate. Croatica Chemica Acta [Internet]. 1992 [pristupljeno 08.03.2021.];65(3):539-546. Dostupno na: https://hrcak.srce.hr/137114
IEEE
D.N. Kevill i M.H. Abduljaber, "The Nature of Nucleophilic Assistance to Ion-Pair Formation. Solvolyses of Cyclohexyl p-Toluenesulfonate", Croatica Chemica Acta, vol.65, br. 3, str. 539-546, 1992. [Online]. Dostupno na: https://hrcak.srce.hr/137114. [Citirano: 08.03.2021.]

Sažetak
The solvolysis of cyclohexyl tosylate has been shown previously both to proceed with nucleophilic assistance from the solvent and to give among the substitution and elimination products those which involve a 1,2-hydride shift. In the present report, specific rate data for solvolysis in 18 solvents at 25.0 °C are shown to give an excellent correlation, using the two-term Grun- wald-Winstein equation, against NT solvent nucleophilicity values and YoTs solvent ionizing power values, with an l value of 0.35 and a m value of 0.85. This indicates that sensitivities to changes in solvent nucleophilicity (Z values) of as large as 0.35 can reflect nucleophilic solvation of a developing carbocation, rather than bimolecular (SN2 + E2) attack. The temperature dependencies of the Z and m values are given consideration.

Hrčak ID: 137114

URI
https://hrcak.srce.hr/137114

Posjeta: 217 *