cyanohydrinlike

Cyanohydrinlike describes chemical motifs or compounds that resemble cyanohydrins in structure or reactivity. A cyanohydrin is formed when a carbonyl compound (an aldehyde or ketone) reacts with hydrogen cyanide or a cyanide source to give a carbon bearing both a hydroxyl and a cyano group. The term cyanohydrinlike is used in the literature to refer to related species that contain the same functional arrangement of a hydroxyl and a nitrile on adjacent atoms or on the same carbon, or to masked forms that can generate cyanohydrins under certain conditions.

Structurally, the hallmark of cyanohydrinlike compounds is a carbon center bearing both a hydroxyl group and a cyano group, typically written as R2C(OH)CN for ketone-derived examples or R-CH(OH)CN for aldehyde-derived ones. Variants may include different substituents around the carbon bearing these two groups, and some related motifs may feature intramolecular hydrogen bonding or stabilization that enables isolation.

Formation and relevance: Cyanohydrin formation occurs via nucleophilic addition of cyanide to carbonyl compounds and is reversible under some conditions. Cyanohydrinlike motifs appear both as direct products and as intermediates in organic synthesis, serving as masked aldehydes or as versatile handles for further transformations (for example, conversion to esters, amines, or nitriles). Classical examples include mandelonitrile from benzaldehyde and acetone cyanohydrin from acetone, which are often cited as prototypical cyanohydrins and reference points for cyanohydrinlike chemistry.

See also: cyanohydrin, masked aldehydes, nitriles, aldehyde chemistry.