Carboximidate
ester of an imidic acid
Carboximidates (or more general imidates) are organic compounds, which can be thought of as esters formed between an imidic acid (R−C(=NR′)OH) and an alcohol, with the general formula R−C(=NR′)OR″.
They are also known as imino ethers, since they resemble imines (>C=N−) with an oxygen atom connected to the carbon atom of the C=N double bond.
Synthesis
Imidates may be generated by a number of synthetic routes, but are in general formed by the Pinner reaction. This proceeds via the acid catalyzed attack of nitriles by alcohols.
Imidates produced in this manner are formed as their hydrochloride salts, which are sometimes referred to as Pinner salts. Carboximidates are also formed as intermediates in the Mumm rearrangement and the Overman rearrangement.
Imidate/amidate anions
An amidate/imidate anion is formed upon deprotonation of an amide or imidic acid. Since amides and imidic acids are tautomers, they form the same anion upon deprotonation. The two names are thus synonyms describing the same anion, although arguably, imidate refers to the resonance contributor on the left, while amidate refers to the resonance contributor on the right. However, they are distinguished when they act as ligands for transition metals, with O-bound species referred to as imidates and N-bound species referred to as amidates.
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