Diels–Alder reaction of fumaronitrile and cyclopentadiene in water: the influence of cosolutes

Abstract

Rates of reaction are reported for the title compounds in aqueous solution. The influence of added salts on the rate of reaction is recorded: alkali-metal salts advance the rate, while tetraethylammonium chloride retards it. Sodium dodecyl sulphate and cetyltrimethylammonium bromide also retard the reaction, while the effect of cyclodextrins depends on their cavity size. The explanation of these phenomena in terms of the hydrophobic effect is considered and extended by measurement of ΔH‡ and ΔS‡ parameters for the reaction.