Methylenecyanamide (CH2═NCN) and (Z)- and (E)-Iminoacetonitriles (NC-CH═NH), Dimers of Hydrogen Cyanide.

(Z)- and (E)-iminoacetonitriles (NCCH═NH), two hydrogen cyanide dimers, are described as key compounds in prebiotic chemistry. Among the many possible dimers of HCN with covalent bonds, even the second on the scale of thermodynamic stability, methylenecyanamide (CH2═NCN), has been investigated little. We show that this compound can be isolated, is stable enough to give an adduct with a nucleophile or a diene, and can be easily generated under prebiotic conditions, highlighting a possible role in this medium. Comparison between isomers shows significant differences in formation and chemical reactivity.