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The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates

Vernon J. Shiner Jr. ; The Department of Chemistry, Indiana University Bloomington, Indiana 47405, USA
Thomas E. Neumann ; The Department of Chemistry, Indiana University Bloomington, Indiana 47405, USA
Bradley B. Basinger ; The Department of Chemistry, Indiana University Bloomington, Indiana 47405, USA

Puni tekst: engleski, pdf (23 MB) str. 1405-1420 preuzimanja: 136* citiraj
APA 6th Edition
Shiner Jr., V.J., Neumann, T.E. i Basinger, B.B. (1996). The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates. Croatica Chemica Acta, 69 (4), 1405-1420. Preuzeto s https://hrcak.srce.hr/135979
MLA 8th Edition
Shiner Jr., Vernon J., et al. "The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates." Croatica Chemica Acta, vol. 69, br. 4, 1996, str. 1405-1420. https://hrcak.srce.hr/135979. Citirano 26.02.2021.
Chicago 17th Edition
Shiner Jr., Vernon J., Thomas E. Neumann i Bradley B. Basinger. "The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates." Croatica Chemica Acta 69, br. 4 (1996): 1405-1420. https://hrcak.srce.hr/135979
Harvard
Shiner Jr., V.J., Neumann, T.E., i Basinger, B.B. (1996). 'The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates', Croatica Chemica Acta, 69(4), str. 1405-1420. Preuzeto s: https://hrcak.srce.hr/135979 (Datum pristupa: 26.02.2021.)
Vancouver
Shiner Jr. VJ, Neumann TE, Basinger BB. The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates. Croatica Chemica Acta [Internet]. 1996 [pristupljeno 26.02.2021.];69(4):1405-1420. Dostupno na: https://hrcak.srce.hr/135979
IEEE
V.J. Shiner Jr., T.E. Neumann i B.B. Basinger, "The Mechanism of Solvolysis of 2,2-Dimethyl-3-pentyl and 1-(1-Adamantyl)propyl Sulfonates", Croatica Chemica Acta, vol.69, br. 4, str. 1405-1420, 1996. [Online]. Dostupno na: https://hrcak.srce.hr/135979. [Citirano: 26.02.2021.]

Sažetak
Solvolysis rates, alpha and beta deuterium isotope rate effects and product yields have been determined for some 1-(1-adamantyl) propyl sulfonate esters, 4, in some ethanol-water, trifluoroethanol- water and hexafluoroisopropyl alcohol-water mixtures. For comparison, similar measurements have been made for solvolysis of 2,2- dimethyl-3-pentyl sulfonates, 5. For the esters 5, the alpha-đ and beta-c?2 effects vary little with solvent in the ranges of 1.164-1.165 and 1.215-1.241, respectively, and only small yields of unrearranged products are formed; it is concluded that the mechanism involves rate determining formation of the secondary cation-ion pair followed by rapid rearrangement. For the adamantyl analogs, 4, the alpha-d effects vary in the different solvents from 1.162 to 1.213 and the beta-đ2 effects vary from 1.339 to 1.649; significant yields of unrearranged and Wagner-Meerwein rearranged (ring expansion) products are formed. The steady state treatment, which had been used previously to fit the results for 1-(1-adamantyl)ethyl esters, was applied to the results for 4; a mechanism which involves partially reversible ionization to the intimate ion-pair followed by competing elimination and solvent separation, to give the substitution products, fits the results reasonably well. 

Hrčak ID: 135979

URI
https://hrcak.srce.hr/135979

Posjeta: 235 *