Talk:Imidazolidinyl urea
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Naming[edit]
- (entitled after beginning of discussion)
I believe the name should be based on urea as original edited but then reverted again
Urea: http://www.acdlabs.com/iupac/nomenclature/79/r79_661.htm and http://www.acdlabs.com/iupac/nomenclature/93/r93_716.htm
So, the name should be: N',N-Methylenebis{1-[3-(hydroxymethyl)-2,5-dioxo-4-imidazolidinyl]urea} with the N',N''' italicized--ChemSpiderMan (talk) 20:35, 24 January 2008 (UTC)
- Thanks for your comment. I understand your intension. As mentioned by the IUPAC rule C-971 (file: r79_661.htm) "Derivatives of urea formed by replacement of hydrogen" may be named "as substitution products of urea". As a matter of fact, both your and my preferred name are constructed in this way, they all end with urea. The difference is, your one is build by multiplicative naming of identical units arranged around a symmetric center, mine by simple substitutive nomenclature. For your case, rule R-1.2.8 (Multiplicative operation) applies. But this rule applied to the molecule we're talking about leads to a different name. Thus, a naming similar to the one you are preferring is quiet possible, but it's not the one mentioned.
- The reason is, the identical units in our molecule have more substituents than the one that is the principal group (i.e. urea). But the multiplicative rule is only to be applied to identical units "whose only substituents are the principal characteristic groups". So the name should be constructed first only using the imidazolidin-4-yl-urea, and than adding the further substituents as prefixes of the entire name with corresponding primed locants. For example: <further substituents>-N,N''-Methylenediimidazolidin-4-yl-urea. But in this example, I'm not sure about numbering/priming because of the many nitrogenium atoms.
- Lastly, no matter which IUPAC rule you apply, R-1.2.8 or the simple substitutive nomenclature, the mentioned name isn't correct IUPAC.
- In terms of priming, I have opt for one other than yours because it is more close to IUPAC to choose locants/primes as low/few as possible, if there is a chose. This may be easier to deal with for people which only have small clue about IUPAC and try to understand. But, since the name actually isn't IUPAC, other numbering/priming may also be correct (and is in use, search [1] for "Imidurea").
- Since the name you mentioned (or similar ones) is widely used, I added it to the box with other names. I also added one with numerical locants, again to help novices.
- Concluding I want to add, that I found the name I put in as the/a IUPAC name at PubChem Substance, and in the past I learned that PubChem is the most reliable source of IUPAC names among the ones I and many others so often use to find out about chemical properties of substances. But of course, I always prove the names also by myself before I rely on them and post them here or somewhere else. In this case, I found the name to be (a) correct one.
- Hope, I could explain my point of view. —Markus Prokott (talk) 23:11, 24 January 2008 (UTC)
- p.s.: I'd like to recommend you, to more often use the "Show preview" button instead of the "Save page" button, when you edit a page until you are rather sure, the result is optimal. Otherwise an article's history will be hard to overview.
- Thanks for the tip about Show Preview. It would have been useful for this article...agreed. The primes really messed me up! I will continue the conversation by email as I need to send you an image.
The names on PubChem are generated by software and while good are also imperfect. What's your approval rate on the software generated names? --ChemSpiderMan (talk) 00:11, 25 January 2008 (UTC)
- I've asked the on-line naming service by ACD/Labs and IUPAC itself. The result was the name: N',N'''-methylenebis{N-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}. However, in the help of the (non-free version of) the service ACD/Labs admits that there may still be some problems with the correct implementation of IUPAC rules, one may be particularly the multiplicative operation. While both the PubChem names and the multiplicative names are produced by software, how can we decide which one is correct? All documents I've read online are diviating from the result the on-line naming service has provided. Is there any Wikipedia rule which help us in this situation decide which name to choose? What about listing both names as (possible and valid) IUPAC names? Nevertheless, IUPAC tells us, that they don't (yet) provide rules to construct unique names, but unambiguous ones.
- Greets —Markus Prokott (talk) 22:17, 25 January 2008 (UTC)
- Update: This second I got your mail. What funny co-incidence, you just use the commercial version of the naming service I mentioned above. But look at that right window of the result display, as you can see, all the listed IUPAC rules doesn't deal with the basic kind of building system that is used to build up the entire name; i.e. simple substitutive nomenclature or multiplicative operation. The question is which one we have to opt for? Or are both of them allowed? All listed rules only deal with the construction of the isolated part of the whole name, except for the very first, which declares urea as the correct parent hydride in the naming procedure – but the parent hydride is not in doubt.
- —Markus Prokott (talk) 22:52, 25 January 2008 (UTC)
- Additional update: I read the rest of your mail. As I conclude, you are deeply involved in IUPAC rules and application of them. Thus I think, I needn't to hesitate to asked you harder questions in terms of IUPAC. So, can you tell me how R-1.2.8 (Multiplicative operation) and Rule C-72 (Assemblies Involving Bi- or Multi-valent Radicals), respectively, support the multiplicative form of name we are talking about? I cannot see how the sentence "whose only substituents are the principal characteristic groups" allows this name. Another conflict for me are rule Rule C-73 (Derivatives of Assemblies of Identical Units) and subrule R-1.2.8.3 (Derivatives of assemblies of identical units), respectively.
- –Markus Prokott (talk) 23:14, 25 January 2008 (UTC)
- Markus..I have asked the head of the nomenclature team for ACD/Name to check the name and provide his feedback. He is a "dyed in the wool" Nomenclature specialist and is engaged in nomenclature literally everyday of his work. He is a much better expert than myself and has sat on IUPAC committees for many years. This is something he cares about and I will post his response when I get it. --ChemSpiderMan (talk) 23:30, 25 January 2008 (UTC)
Wonderful! :-) —Markus Prokott (talk) 17:20, 26 January 2008 (UTC)
- Markus: Here is the suggested "Manually created" IUPAC Name:
1,1'-methylenebis{3-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} WHat do you think?--ChemSpiderMan (talk) 17:58, 29 January 2008 (UTC)
- I think I must agree, if two experienced nomenclaturists vote for the multiplicative kind of naming. Although I was really looking forward for an explanation of why your collegue constructed the name in this way. Nevertheless, it's (except for the parenthesizing) just the second multiplicative form which I gave for the other names. So, I'm proud to see that at least my steps of constructing/proving the name, that where beyond the decision between multiplicative and simple naming, have been correct.
- Thanks —Markus Prokott (talk) 17:08, 30 January 2008 (UTC)
Done I added the name
1,1'-methylenebis{3-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}
today (but only as “erroneous old structure”) and moved the other name to the other names' section. See [2]. —Markus Prokott (talk) 10:26, 23 February 2008 (UTC)
Why is the compendial status necessary[edit]
--124.78.210.114 (talk) 09:33, 11 February 2010 (UTC)
--124.78.210.114 (talk) 09:34, 11 February 2010 (UTC)