How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
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3$\begingroup$ @Maurice Why exactly do you think there would be no O-benzoil derivative of hydroxylamine? $\endgroup$– MithoronCommented Jan 6 at 15:23
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$\begingroup$ Let's say it does exist, but is so unlikely that we are compelled to suspect a mistake. $\endgroup$– Ivan NeretinCommented Jan 6 at 15:32
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$\begingroup$ im new to organic chemistry. @IvanNeretin why is it so unlikely? $\endgroup$– kzmomCommented Jan 6 at 16:12
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4$\begingroup$ Sort of cheating, but the CAS number for your compound is 54495‐98‐6 (added as image metadata) so you can learn more about the molecule. ChemSpider might be a good start. $\endgroup$– andselisk ♦Commented Jan 6 at 21:57
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2$\begingroup$ @IvanNeretin Not only is it a known compound, it is commercially available - as O-benzoylhydroxylamine biosynth.com/p/ECA49598/… $\endgroup$– WaylanderCommented Jan 7 at 8:34
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1 Answer
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According to the last printed version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), the retained name hydroxylamine was used for the construction of the preferred name.
P-68.3.1.1.1 Hydroxylamines
The retained name ‘hydroxylamine’ is a preselected name and designates the structure $\ce{H2N-OH}$. It is a functional parent compound allowing full substitution even, as an exception, on the oxygen atom. (…)
P-68.3.1.1.1.2 Substitution on the oxygen atom of hydroxylamine
Substitution of hydroxylamine on the oxygen atom by hydrocarbyl or acyl groups is expressed as O-substitution. (…)
$\ce{H2N-O-CO-C6H5}$
O-benzoylhydroxylamine (PIN)
However, this was changed on 3 March 2021. The PIN is now given as aminooxy(phenyl)methanone.
(I am not sure if this still contains a mistake and should actually read (aminooxy)(phenyl)methanone.)
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$\begingroup$ but isnt this some sort of ester? i dont understand $\endgroup$– kzmomCommented Jan 6 at 16:13
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$\begingroup$ Here it should be some sort of benzoate right? something like aminomethyl benzoate? $\endgroup$– kzmomCommented Jan 6 at 16:20
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$\begingroup$ @kzmom Hmm, but hydroxylamine is not an alcohol, so it cannot be an ester, AFAIK. $\endgroup$– PoutnikCommented Jan 6 at 16:27
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$\begingroup$ @kzmom One could in principle call it azanyl benzoate, but it's rather an amide analogue made with hydroxylamine instead of ammonia. Something like one tried to make peroxyacid amide. $\endgroup$– MithoronCommented Jan 6 at 16:33
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1$\begingroup$ @kzmom Peroxo implies two oxygen atoms - I already mentioned this analogy, but it's useless in nomenclature. Only group of compounds this belongs is O-acylhydroxylamines. $\endgroup$– MithoronCommented Jan 7 at 16:30