I'm don't have a background in chemistry but I've been doing a project on computer aided molecular design and one of the resulting molecules was:

I'm having trouble naming this molecule let alone research if it is viable. I would appreciate any help in either naming or disqualifying it as infeasible.

  • $\begingroup$ Something along the lines of difluoro(methyl)amine. You also might find dx.doi.org/10.1021/acs.jpca.5b05157 interesting. $\endgroup$
    – andselisk
    Jan 9 at 19:20
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    $\begingroup$ Maybe not so simple considering that the PIN for $\ce{CH3-NH2}$ is methanamine but the PIN for $\ce{CH3-NH-F}$ surprisingly is N-methylhypofluorous amide and not N-fluoromethanamine. $\endgroup$
    – Loong
    Jan 9 at 19:34
  • $\begingroup$ @Loong The again, is OP even asking about PIN, and what about "feasibility"? The question isn't clear. $\endgroup$
    – Mithoron
    Jan 9 at 20:07
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    $\begingroup$ @Mithoron Usually, we cannot be sure if an OP even knows what a PIN is, so we cannot expect that a nomenclature question will explicitly ask for the PIN. Generally, we recommend answering such questions with the PIN (see meta), but feel free to include other names in your answer. $\endgroup$
    – Loong
    Jan 9 at 20:17
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    $\begingroup$ The compound is definitely viable and has been subject to a study. The compound was made by reacting dinitrogen tetrafluoride with methyl iodide. (m.p. -114.8 °C, b.p. -16°C and density of 1.099 at -20°C). @Loong The compound was previously named Methyldifluoroamine before changing the name by considering it an amide derivative as per new IUPAC rules. $\endgroup$ Jan 10 at 6:16

1 Answer 1


The IUPAC recommendations on this matter have been changed. Compounds such as $\ce{R{-}NH{-}Cl}$, $\ce{R{-}NH{-}NO}$, and $\ce{R{-}NH{-}NO2}$ are now named as derivatives of amides (see P-

The current version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) reads as follows:


Traditionally, substitution on the nitrogen atom of amines and imines was allowed for all characteristic groups cited as prefixes (see Table 5.1). This approach is maintained in these recommendations, unless a higher class is formed that must be named in accordance with the seniority of classes (see P-41).
This new rule is applied to prefixes such as Cl and other halogen atoms, $\ce{{-}BrO}$ and other acyl similar groups, $\ce{{-}NO}$, $\ce{{-}NO2}$, $\ce{{-}OR}$, $\ce{{-}SO2{-}R}$, $\ce{{-}SO{-}R}$, and even $\ce{{-}OH}$ groups and chalcogen analogues.

Thus, the preferred name for the compound that is given in the question is N-fluoro-N-methylhypofluorous amide and not N,N-difluoromethanamine.

A similar example given in the Blue Book is $\ce{CH3{-}N{-}(NO2)2}$, which is named N-methyl-N-nitronitramide and not N,N-dinitromethanamine.

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    $\begingroup$ It could be that this is still not the correct answer, since there was a correction to the Blue Book concerning the N locants in 2021. $\endgroup$
    – Loong
    Jan 9 at 20:06

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