Chemistry · Ch 13 — Organic Nitrogen Compounds
Introduction to Cyanides and Isocyanides
13.4.1
Introduction to Cyanides and Isocyanides
Cyanides and isocyanides are the derivatives of hydrocyanic acid's two tautomeric forms, hydrogen cyanide and hydrogen isocyanide. Alkyl cyanides (R-C#N) are named in IUPAC as 'alkanenitriles' (their aryl counterparts as 'arenecarbonitrile'), while their common names often end in '-onitrile' (e.g. acetonitrile, propiononitrile, butyronitrile). A cyano group substituent elsewhere in a m …
Figure ~fig-13.4.1-tautomersTautomeric forms of hydrocyanic acid
What this figure shows. Two linked structures showing HCN's tautomerism: hydrogen cyanide, H-C#N (hydrogen bonded to carbon, carbon triple-bonded to nitrogen), and hydrogen isocyanide, H-N#C (hydrogen bonded to nitrogen instead, nitrogen bonded to a divalent carbon bearing a lone pair). …
Table 13.7Nomenclature of representative cyanides
| Compound (common name) | Structural formula | IUPAC name |
|---|---|---|
| Acetonitrile | CH3-CN | Ethanenitrile |
| Propiononitrile | CH3-CH2-CN | Propanenitrile |
| Butyronitrile | CH3-CH2-CH2-CN | Butanenitrile |
| Isobutyronitrile | (CH3)2CH-CN | 2-Methylpropanenitrile |
| Benzonitrile | C6H5-CN | Benzenecarbonitrile |
| -- | H3C-CH(CN)-CH2-COOH | 3-Cyanobutanoic acid |