Nomenclature of substituted amines is done with the N-locants, with the N being used to indicate that a group is connected to the methyl group. I was wondering, therefore, on how to properly name a substituted diamine.

I found this source from the University of Calgary, here, which recommended to use N, N', N'', etc locants for compounds with multiple substituted amines. However, their examples are all with symmetrical diamines, and it is apparent that using the N, N' locants only works because of the molecule's symmetry. Thus, my question is: how can we name substituted diamines properly, such as the one below?

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Would it be N,N,N'-trimethyl,3,5-diaminopent-1-ene or N,N',N'-trimethyl,3,5-diaminopent-1-ene, or something else?


According to the current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), superscript arabic numbers are used to differentiate the nitrogen atoms.

P-16.9.2 Superscript arabic numbers, which are the locants of the parent structure, are used to differentiate the nitrogen atoms of di- and polyamines, di- and polyimines, di- and polyamides, except for geminal amines, imines, and amides.

In particular, note that the superscript arabic numbers correspond to the locants of the parent structure. Since the parent structure of the compound that is given in the question is pent-4-ene-1,3-diamine, the locants are 1 and 3. Therefore, the complete name for the substituted compound is N1,N3,N3-trimethylpent-4-ene-1,3-diamine.

  • $\begingroup$ If a molecule WAS geminal, how would it be named and/or numbered? $\endgroup$
    – Kurt Hikes
    Jan 15 at 22:41

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