Re: Nomenclature: carbamyl, carbamoyl

On 2006-05-04, sanlosinst@xxxxxxxxxxx <sanlosinst@xxxxxxxxxxx> wrote:
Jimchip wrote:
On 2006-05-03, sanlosinst@xxxxxxxxxxx <sanlosinst@xxxxxxxxxxx> wrote:
Hi. I'm a little unsure about the nomenclature of certain organic
functional groups. I've seen molecules with this functional group:

-O-C(=O)-NH2

The way I start with these is based on the parent
compound: H-O-C(=O)-NH2 carbamic acid

R-O-C(=O)-NH2 ester of carbamic acid...alkyl carbamate.

The R0- has a carbamyl group attached (e.g. CH3-C(=O)- acetyl)

-C(=O)-NH2


Is this a carbamyl group or a carbamoyl group? I would take a guess
that this is carbamoyl, and that the same without the first -O- is
carbamyl, ie.

-C(=O)-NH2

I would call Cl-O-C(=O)-NH2 carbamyl chloride.

www.chemfinder.com calls this 'carbamic chloride' (no other synonyms):

Cl-C(=O)-NH2

I like CambridgeSoft but that makes so sense to me...common names from the
urethane polymer people?

www.chemfinder.com calls this 'carbamic chloride, diethyl' and 'diethyl
carbamyl chloride':

Cl-C(=O)-NEt2

I definitely prefer 'diethyl carbamyl chloride'.


Carbamoyl would be a name derived from carbamoic acid (e.g. benzoic acid,
benzoyl) and would mean the same thing. But there is no carbamoic acid.

Carbamoyl does get used when it's one acid root of an anhydride, so your
idea about the first O would work. It's more of a biochemical addition, IMO.

www.chemfinder.com also has a listing for a compound with the synonyms
'carbamoyl-2,4,6-trichlorobenzoic acid' and
'carbamyl-2,4,6-trichlorobenzoic acid'. This has

R-C(=O)-NH2

with the leftmost bond (as written above) being a C-C bond with no
intervening O.

Once again, that makes no sense to me. I could probably say the same thing
about the English language in many cases :)


So it seems that 'carbamic', 'carbamyl' and 'carbamoyl' are all used
interchangeably for

-C(=O)-NH2

Does anyone know if IUPAC or anyone else has official listings of what
these terms mean? I had a quick look on the IUPAC website but I
couldn't find anything.

I think with things like this one has to realize that a rational approach to
naming compounds (many times using a group name) will get you to the
compound in question and one finally finds out how to formally name it along
the way.

Thanks for any help,

Samuel

--
I would have never thought, initially, that 2-phenylethylamines would be
listed by CAS as "styrylamines"
.