Hydration of cn bonds in heteroaromatic substances

Many aromatic N‐heterocycles add water across the CN double bond. Methods are described for recognizing this phenomenon and for diagnosis of the site of attack. These methods are extended to the determination of (a) the ionization constants of unstable states (whether hydrated or anhydrous), (b) the ratio of hydrated to anhydrous forms at equilibrium, and (c) the rate constants of hydration. The features that stabilize hydration in a molecule are discussed. The literature through 1965 and 1966 is reviewed with special reference to the emergence of new principles, such as di‐hydration and the shifting of hydration within a molecule.