# Naming of an organic compound containing nitrogen and fluoride

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.

• Something along the lines of difluoro(methyl)amine. You also might find dx.doi.org/10.1021/acs.jpca.5b05157 interesting. Jan 9 at 19:20
• 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. Jan 9 at 19:34
• @Loong The again, is OP even asking about PIN, and what about "feasibility"? The question isn't clear. Jan 9 at 20:07
• @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. Jan 9 at 20:17
• 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. Jan 10 at 6:16

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-67.1.2.6).

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

P-62.4 N-SUBSTITUTION OF AMINES AND IMINES BY HETEROATOMS

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.

• 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. Jan 9 at 20:06