[bobbydigital]

Hi, all. I'm classifying a database of organic substances by the functional groups within each substance -- this is done programmatically using SMARTS strings that I design. I'm currently trying to write a "definitive" list of functional groups containing one or more nitrogen atoms.

From various o-chem books and online resources I've put together a list of ~20 different functional groups that contain nitrogen. However, I have not found a _comprehensive_ list of functional groups and their names.

I assume that IUPAC might have something like this, and I've searched the IUPAC gold book. However, this requires that you already know the name of the functional group!

Does anyone know of a comprehensive way to get a list of all nitrogen-containing functional groups?

[Nobby]

Probably with Chemical abstracts, if you write down the formulas:

-NO, -NO₂, -NO₃, =NOH, -NH₂ =NH, -NHOH, -NH-NH₂, -N=N-, -CN, -N=C, etc.

[AMEDIO]

http://en.wikipedia.org/wiki/Functional_group

this will help
 

[bobbydigital]

I did find the wikipedia page, which gave the basic functional groups. However, there are many not listed on that page.

Also, I haven't been able to find a way to use Chemical Abstracts to accomplish this task.

I've been digging through Jerry March's _Advanced_Organic_Chemistry_ book, but the functional groups (to my knowledge) are not listed in a table. However, they do appear in Appendix B, perhaps comprehensively, however only the names (and not the formula) for each functional group is given. Here is my current list of Nitrogen-containing functional groups:

amide
amine
azide
azine
azo
carbamate
cyanate
diazo
diazonium
enamine
hydrazine
hydrazone
hydroxamic acid
hydroxylamine
imide
imine
nitrate
nitrile
nitrite
nitro
nitrosamine
nitroso
nitroso
oxime
sulfinamide
sulfinylimine
sulfonamide
sulfonylimine

[Honclbrif]

http://en.wikipedia.org/wiki/Amidine
http://en.wikipedia.org/wiki/Ketenimine

[Honclbrif]

"trying to write a "definitive" list of functional groups containing one or more nitrogen atoms."

Kind of a tall order. Here are some that come to mind, excluding the nitrogen heterocycles.

http://en.wikipedia.org/wiki/Isocyanate
http://en.wikipedia.org/wiki/Isothiocyanate
http://en.wikipedia.org/wiki/Aziridine
http://en.wikipedia.org/wiki/Nitrene
http://en.wikipedia.org/wiki/Triazene
Imidoate RC(=NR')OR''

[bobbydigital]

Thanks, Honclbrif, I'll add those to my list!
I'm also excluding heterocycles for the moment.

[DrCMS]

What about http://en.wikipedia.org/wiki/Silazane ?

[nox]

I think it'd be more sensible if you excluded the following:

http://en.wikipedia.org/wiki/N-oxide
http://en.wikipedia.org/wiki/Azoxy
http://en.wikipedia.org/wiki/Carbodiimide
http://en.wikipedia.org/wiki/Cyanamide
http://en.wikipedia.org/wiki/Dithiocarbamate
http://en.wikipedia.org/wiki/Guanidine
http://en.wikipedia.org/wiki/Isonitrile
http://en.wikipedia.org/wiki/Nitroamine
http://en.wikipedia.org/wiki/Nitrone
http://en.wikipedia.org/wiki/Nitronate
http://en.wikipedia.org/wiki/Phosphoramidite
http://en.wikipedia.org/wiki/Phosphoramidate
and a whole slew of other compounds with a P-N bond
http://en.wikipedia.org/wiki/Semicarbazide
http://en.wikipedia.org/wiki/Semicarbazone
http://en.wikipedia.org/wiki/Sulfoximine
http://en.wikipedia.org/wiki/Thioamide


http://en.wikipedia.org/wiki/Cyanate
http://en.wikipedia.org/wiki/Thiocyanate

http://goldbook.iupac.org/V06609.html

[bobbydigital]

Nox, thanks for the input!
But why do you think those groups should be excluded?
For example, Isonitrile and Nitroamine seem perfectly reasonable to me.

[nox]

OOOPS

I totally forgot to delete the first sentence, I was going to make a separate list of things that should be excluded but I forgot to follow up on that

Basically, I was saying you probably want to exclude any functional groups containing P-N or S-N bonds, unless it's the really common ones like sulfonamides and such. Otherwise the list gets a bit ridiculous.