Isothiocyanate
salt or ester of isothiocyanic acid
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula R−N=C=S. Isothiocyanates are the more common isomers of thiocyanates, which have the formula R−S−C≡N.
Occurrence
Many isothiocyanates from plants are produced by enzymatic conversion of metabolites called glucosinolates. A prominent natural isothiocyanate is allyl isothiocyanate, also known as mustard oils.
Cruciferous vegetables, such as bok choy, broccoli, cabbage, cauliflower, kale, and others, are rich sources of glucosinolate precursors of isothiocyanates.
Structure
The N=C and C=S distances are 117 and 158 pm. By contrast, in methyl thiocyanate, N≡C and C−S distances are 116 and 176 pm.
Typical bond angles for C−N=C in aryl isothiocyanates are near 165°. Again, the thiocyanate isomers are quite different with C−S−C angle near 100°. In both isomers the SCN angle approaches 180°.
Synthesis
Isothiocyanates can be prepared by treating organic dithiocarbamate salts with lead nitrate or tosyl chloride:
They generally cannot be prepared from alkylation of thiocyanate salts, as the ion's S terminus is much more nucleophilic. However, stabilized carbocations can reionize and rearrange to the thermodynamically preferred isothiocyanate.
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