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Deuterium Isotope Effects On The Solvolysis Rates Of Cyclopentyl Brosylates And Tosylates, Jimmie D. Christen

Doctoral Dissertations

"The brosylates and tosylates of cyclopentanol and its 1-d₁, c̲i̲s̲-2-d₁, t̲r̲a̲n̲s̲-2-d₁, and 2,2,5,5-d₄ analogs have been synthesized and their solvolysis rates measured at 25° in 70% vol. ethanol-water. The solvoylsis reactions were monitored by a conductance method. The isotope effects, k_H/k_D, observed for the brosylates and tosylates of each of the isotopically substituted cyclopentyl alcohols are as follows: 1-d₁-brosylate (1.1869) and 1-3₁-tosylate (1l1836); c̲i̲s̲-2-d₁-brosylate (1.1533) and c̲i̲s̲-2-3₁-tosylate (1.1577); t̲r̲a̲n̲s̲-2-d₁-brosylate (1.1803) and t̲r̲a̲n̲s̲-2-d₁-tosylate (1.1765); 2,2,5,5-d₄-brosylate (1.8881) and 2,2,5,5-d₄-tosylate (1.8863). The closeness in magnitude of the isotope effects for the c̲i̲s̲- and t̲r̲a̲n̲s̲-isomers is important in that it …