Can amide ($\ce{RCONH2}$) form Schiff base? When I searched for it, most papers deal with aliphatic amines. Some paper conducted synthesis with amide-containing compound, but iminization occured at β-nitrogen, (e.g. $\ce{RCON^1HN^2H2}$, iminization occured at $\ce{N^2}$) not α-nitrogen. Can α-nitrogen in amide also form Schiff base?

  • $\begingroup$ The lone pair on amide $\ce{N}$ is not fully available to make an imine with carbonyl group (it is conjugated with nearby carbonyl; e.g., recall peptide bonds in protein). $\endgroup$ Sep 24 at 7:19
  • $\begingroup$ The reaction you might expect to give a Schiff base i.e. condensation of an amide RCONH2 and an aldehyde R'CHO gives a dimeric species where 2 amides add to the aldehyde to give (RCONH)2CHR' pubs.acs.org/doi/10.1021/ja01335a085 $\endgroup$
    – Waylander
    Sep 24 at 13:27

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