The structure of prussic acid has been a subject of constant interest ever since Gautier, by his discovery of the isocyanides provided an alternative formula for the acid. In general, opinion has leaned towards the view that the free acid is a cyanide rather than an isocyanide. In particular, Wade regarded its relatively unobjectionable physiological properties as evidence of a cyanide structure; but evidence of an isocyanide structure has been found by Peratoner and Palazzo in the conversion of the acid into methyl isocyanide by the action of diazomethane. A possible compromise may be found in the suggestion, already made in Butlerow’s classical paper “Ueber Isodibutylen,” that prussic acid may be an example of reversible isomeric change, as represented by the scheme CH 3 . C ≡ N ← H. C ≡ N ⥧ H. N ═ C → CH 2 . N ≡ C Methyl cyanide. Prussic acid. Methyl iso cyanide.
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