Hydrogen Isotope Exchange Reactions of Organic Compounds in Liquid Ammonia

Abstract

Publisher Summary This chapter focuses on hydrogen isotope exchange reactions of organic compounds in liquid ammonia. The study of hydrogen isotope exchange reactions in organic compounds yields valuable information about the reactivity and the structure of these compounds. In this connection, it is particularly important to have data on the kinetics of hydrogen exchange in CH bonds. The detailed study of the properties of liquid ammonia in its role as a solvent, the various chemical reactions with it and in it as a medium, and the physicochemical study of ammonia solutions of inorganic and organic substances have been the major achievement. Experiments on hydrogen exchange in liquid ammonia have been carried out in the temperature range between -40° and 120° with 0.01N–3N potassium amide solutions. Liquid ammonia is a very suitable solvent for studying the salt effect, because many organic substances and salts are easily soluble in it. The kinetic isotope effect is of importance in the interpretation of the mechanism of hydrogen exchange reactions in protophilic solvents. The study of hydrogen exchange in saturated hydrocarbons is hindered by their poor solubility in liquid ammonia. For this reason, the reacting mixtures must be stirred during prolonged heating and the results of experiments are only qualitative in character.