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Original scientific paper

Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System

Y. Chiang ; Department of Chemistry, University of Toronto, Toronto, Ontario M5S 1A1, Canada
A. J. Kresge ; Department of Chemistry, University of Toronto, Toronto, Ontario M5S 1A1, Canada
P. A. Obraztsov ; Department of Chemistry, University of Toronto, Toronto, Ontario M5S 1A1, Canada
J. B. Tobin ; Department of Chemistry, University of Toronto, Toronto, Ontario M5S 1A1, Canada

Fulltext: english, pdf (19 MB) pages 615-623 downloads: 121* cite
APA 6th Edition
Chiang, Y., Kresge, A.J., Obraztsov, P.A. & Tobin, J.B. (1992). Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System. Croatica Chemica Acta, 65 (3), 615-623. Retrieved from https://hrcak.srce.hr/137121
MLA 8th Edition
Chiang, Y., et al. "Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System." Croatica Chemica Acta, vol. 65, no. 3, 1992, pp. 615-623. https://hrcak.srce.hr/137121. Accessed 21 Apr. 2021.
Chicago 17th Edition
Chiang, Y., A. J. Kresge, P. A. Obraztsov and J. B. Tobin. "Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System." Croatica Chemica Acta 65, no. 3 (1992): 615-623. https://hrcak.srce.hr/137121
Harvard
Chiang, Y., et al. (1992). 'Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System', Croatica Chemica Acta, 65(3), pp. 615-623. Available at: https://hrcak.srce.hr/137121 (Accessed 21 April 2021)
Vancouver
Chiang Y, Kresge AJ, Obraztsov PA, Tobin JB. Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System. Croatica Chemica Acta [Internet]. 1992 [cited 2021 April 21];65(3):615-623. Available from: https://hrcak.srce.hr/137121
IEEE
Y. Chiang, A.J. Kresge, P.A. Obraztsov and J.B. Tobin, "Acid-Catalyzed Hydration of 1-Methylcycloheptene and Methylenecycloheptane. Construction of the Complete Free Energy Profile for Olefin-Alcohol Interconversion in the 1-Methylcycloheptyl System", Croatica Chemica Acta, vol.65, no. 3, pp. 615-623, 1992. [Online]. Available: https://hrcak.srce.hr/137121. [Accessed: 21 April 2021]

Abstracts
Rates of the reversible hydration of 1-methylcycloheptene (ENDO) to 1- methylcycloheptanol (ROH) and the essentially irreversible hydration of ethylenecycloheptane (EXO) to ROH, plus the position of equilibrium between ENDO and ROH, were determined in concentrated aqueous perchloric acid solution at 25 °C. The results, together with a literature value of the ENDO : EXO equilibrium ratio, allow dissection of the experimental data into hydronium-ion catalytic coefficients for the following individual processes: ENDO-> ROH, *H+ = 102 x 10~3 NT1 s"1; EXO-ROH, *„ + = 3.53 x 1CT3 NT1 s_1; ROH-ENDO, *H+ = 2.17 x lCT5 M'1 s'1, and ROH-EXO, *H+ = 1.01 x 10~6 M-1 s"1. Combination of these results with a previous estimate of the barrier to reaction of tertiary carbocations with water leads to a complete free energy profile for this system.

Hrčak ID: 137121

URI
https://hrcak.srce.hr/137121

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