Chemical nomenclature

Off-topic conversations and chit-chat.

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Oh I am so frustrated with chemical nomenclature. I'm so frustrated that I'm almost enjoying the process of being frustrated. Natural product chemistry is where it comes into its own, truly antisocial, illogical, unhelpful, self-contradictory and weird self:
(1) Why can't people do a Google search before naming their favourite discovery? If the authors of a 2012 J. Agric. Food Chem. paper had googled for the name they chose for a novel product from Manuka honey, "Leptosin", they would have realised the name had already been in use for decades, for an aurone pigment of snapdragon. There are other examples too; it is unhelpful to have the same trivial name used for multiple products, particularly when they appear in related fields (both Leptosins are plant phenolics).
(2) So perhaps authors shouldn't be allowed to make up their own trivial names? Let's trust IUPAC, the people who decided it was a good idea to reverse the order of numbering on the quinic acid ring of chlorogenic acid, thereby converting 3-caffeoylquinic acid to 5-caffeoylquinic acid. Chlorogenic already had history (having nothing to do with chlorophyll or chlorine). But now it's doomed to a literature where one cannot tell what chemical is being discussed, without knowing whether the authors are aware of the change (Sigma still use the pre-1976 nomenclature). People have written whole papers on the nomenclature of chlorogenic acid.
(3) OK, so if we don't want IUPAC making changes that are probably founded on good logic, but doomed to creating unending chaos, we should stick to the numbering that tradition has handed down. Yes, we've done this with flavonoids, where carbon 1 is an oxygen, and two carbons have no number whatsoever. This doesn't matter, as they're both in positions that can never be substituted, but there are two other carbons that can't be substituted and yet are numbered. Who knows. Go figure (but preferably consistently).
(4) Of course life's safe if we stick to logical computerised naming systems. I'm off to continue working on SVILRWHEUBXRMG-JJRVVBIQSA-N. Oh yes, I love InChI keys too.
I'm with you on this. Just like with the EPA and regulating agencies I have to deal with.

Drinking water regulations name the analytes: Trichloroethylene, Tetrachloroethylene, o-Chlorotoluene, p-Chlorotoluene.

Waste water regulations name the analytes: Trichloroethene, Tetrachloroethene, 2-Chlorotoluene and 4-Chlorotoluene.

Also I run into the naming conventions where one report wants Dibromochloromethane and another wants Chlorodibromomethane. From my memory the Di is ignored and the halogens are listed in alphabetical order, instead of including the Di as part of the halogen name before applying alphabetical ordering. (which means Dibromochloromethane is the correct name)

And those are just the easy ones to try to keep straight :)
The past is there to guide us into the future, not to dwell in.
I remember something in the 1970s in our lab: tech was in a hissy fit because method called for methylene chloride, and all we had was dichloromethane
And let us not forget the MSDS for dihydrogen monoxide:
http://dhmo.org/msdsdhmo.html
:lol:
-- Tom Jupille
LC Resources / Separation Science Associates
tjupille@lcresources.com
+ 1 (925) 297-5374
tom jupille wrote:
And let us not forget the MSDS for dihydrogen monoxide:
http://dhmo.org/msdsdhmo.html
:lol:


I have always gotten a laugh out of that one :)

If only people would stop believing in the HHO fad though. I don't know how many people have come to me asking to show them how to make HHO so they can run their vehicle on water.

Ran into another naming problem this week with someone not knowing what to report for a PT result.

Methyl-tertButyl Ether
tert-ButylMethyl Ether
MTBE
TBME

Difficult to include all the synonyms on the report from the instrument for the non-chemist technicians.
The past is there to guide us into the future, not to dwell in.
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