• The effect of hydrophobic-lipophilic interactions on chemical reactivity. 9. Putting the spotlight on lipophilic forces in solvent-effect studies

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    • Keywords


      Hydrophobic-lipophilic interactions; chemical reactivity; solvent-effect studies; hydrolysis rate constant; lipophilicity order

    • Abstract


      The hydrolytic rate constants of thep-nitrophenyl esters of acetic, octanoic, dodecanoic and hexadecanoic acids in six aquiorgano binary mixtures of graded compositions at various initial substrate concentrations were measured and discussed in terms of the hydrophobic-lipophilic interactions between the substrate molecules, and the organic cosolvents which were MeOH, Me2SO, 1, 4-dioxane, 1,2-dimethoxyethane,n-propanol andt-butanol. The accelerating or retarding effects of the organic cosolvents on the rate constants of hydrolysis were found to be directly related to the lipophilicities of the solvents which were changed either by changing the content (ϕ) or the nature of the organic cosolvent. The classification or ordering of the six solvents on the basis of their solvent effects were found to conform to the lipophilicity order derived from Rekker's Σf values. The results support the proposition that lipophilic interactions can play an important role in solvent effects of aqueous binaries.

    • Author Affiliations


      Xi-Kui Jiang1 Xing-Ya Li1 Bang-Zhou Huang1

      1. The Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu, Shanghai, China
    • Dates

  • Journal of Chemical Sciences | News

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