I am trying to create a proflavine derivative containing a 1,2,4-oxadiazole-5-one functional group, the first step produces an interesting functional group that I have no idea how to name:


I am trying to find literature on the above functional group so I can analyze proton NMR to see if I have actual created the above molecule.

  • $\begingroup$ Does the $\ce{-NH-}$ group in $\ce{[Pro]-NH-CH=N-OH}$ correspond to one of the $\ce{-NH2}$ groups of proflavine? $\endgroup$ – user7951 Sep 15 '20 at 8:49
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    $\begingroup$ The HC=N-OH part is usually called an aldoxime, so I might say a "formamide aldoxime" if I were describing it to someone. $\endgroup$ – Andrew Sep 15 '20 at 12:48
  • $\begingroup$ IUPAC aside, such compounds are usually called amidoximes. $\endgroup$ – Mithoron Sep 15 '20 at 22:57

According to Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), the preferred IUPAC name of the compound $\ce{H2N-CH=NH}$ is methanimidamide. The name formimidamide may be used in general nomenclature. The name formamidine is no longer recommended.

The letter locants ‘N’ and ‘N'’ are used to differentiate among the different nitrogen atoms. Thus, the compound $\ce{R-NH-CH=N-OH}$ would be named as N'-hydroxy-N-…methanimidamide.


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