Open AccessMolecular structure and physical properties of prussic acid. Part I. —Refractive dispersion of prussic acid and its homologues
Author(s) -
Thomas Martin Lowry,
Scott Henderson
Publication year - 1932
Publication title -
proceedings of the royal society of london. series a, containing papers of a mathematical and physical character
Language(s) - English
Resource type - Journals
eISSN - 2053-9150
pISSN - 0950-1207
DOI - 10.1098/rspa.1932.0096
Subject(s) - cyanide , diazomethane , isocyanide , chemistry , stereochemistry , organic chemistry , medicinal chemistry
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 CH3 . C ≡ N ← H. C ≡ N ⥧ H. N ═ C → CH2 . N ≡ C Methyl cyanide. Prussic acid. Methyliso cyanide.