Talk:Organofluorine chemistry

Orphaned references in Organofluorine chemistry

I check pages listed in Category:Pages with incorrect ref formatting to try to fix reference errors. One of the things I do is look for content for orphaned references in wikilinked articles. I have found content for some of Organofluorine chemistry's orphans, the problem is that I found more than one version. I can't determine which (if any) is correct for this article, so I am asking for a sentient editor to look it over and copy the correct ref content into this article.

Reference named "Lemal2004":

• From Perfluorooctanoic acid: Lemal DM.: "Perspective on fluorocarbon chemistry" J Org Chem. 2004 Jan 9;69(1):1-11.
• From Hexafluoroacetone: Lemal DM. "Perspective on Fluorocarbon Chemistry" J Org Chem. 2004, volume 69, p 1-11. doi:10.1021/jo0302556

I apologize if any of the above are effectively identical; I am just a simple computer program, so I can't determine whether minor differences are significant or not. AnomieBOT⚡ 22:42, 8 November 2008 (UTC)

This article should explain chemistry

Smokefoot, are you serious about this article explaining fluorine chemistry like the articles organic chemistry, physical chemistry, and analytical chemistry, or are you seeking to create a new fluorocarbon page? I just want to check on that while you work on it. Thanks. -Shootbamboo (talk) 23:43, 8 November 2008 (UTC)

This article will eventually expand to cover organofluorine chemistry. The field is huge and the undertaking correspondingly large, the articles that you referred to required years of effort. This burden is one of the primary reasons that I opposed re-engineering fluorocarbon. --Smokefoot (talk) 23:57, 8 November 2008 (UTC)

Well I wish you would have shared that because I ask: would you welcome my assistance? In good faith I am offering my assistance to you, as I know the contribution required to have a nice page on fluorine chemistry will take substantial work. Thanks. -Shootbamboo (talk) 00:07, 9 November 2008 (UTC)

Sorry for not being more communicative about my plans - I was trying to do that through the talk page on fluorocarbon where I discussed implementing Itub's plan. Of course all of these projects are collaborative. Much of the information that I intended to provide is fairly generic on the chemistry, whereas your interests seem to be exclusively on the environmental and toxicology aspects. Equally pressing, and an area where you may have useful knowledge, is the newly fledged carbon-fluorine bond. That would be great if you hacked away at that. And I will look to lend a hand, and maybe we can trade off.--Smokefoot (talk) 00:40, 9 November 2008 (UTC)

Sounds great. True, I definitely keep an eye out for environmental and toxicological issues, but I do not want to known as a single-minded editor. I hope you see that in my efforts to describe the properties of fluorocarbons. I am looking forward to learning more about organofluorine chemistry. -Shootbamboo (talk) 00:50, 9 November 2008 (UTC)

Merge tag (Organofluorine)

It makes no sense to have separate articles about organofluorine compounds about organofluorine chemistry. One cannot say much about organofluorine chemistry without talking about organofluorine compounds; the two topics are strongly intertwined. The only reason the organofluorine article exists is because it is a POV fork, something which goes against policy. As precedent, I know only of a couple of cases in Wikipedia where the "chemistry" and the "compounds" have separate articles: organic chemistry/organic compound and inorganic chemistry/inorganic compound. Even those two are a bit debatable, but arguably they are cases of summary style, and those two fields are orders of magnitude larger than organofluorine chemistry (no disrespect to organofluorine chemists intended). In contrast, we have at least a dozen articles about organo______ chemistry where, reasonably enough, there is no arbitrary split between the "chemistry" and the "compounds". --Itub (talk) 10:46, 10 November 2008 (UTC)

Itub. A POV fork? Thats a gigantic accusation. I know my edits have been bold, and I have probably angered you more than once, but you know why I started the organofluorine page. Because pharmaceuticals and fluoroacetic acid are not fluorocarbons, and I think a short page on C-F bond containing molecules is in order. I repeated that multiple times on the fluorocarbon talk page. I advise readers of this post to withhold judgment on this issue temporarily until a hopeful agreement can be reached between these two "warring" editors. Thanks. -Shootbamboo (talk) 03:13, 11 November 2008 (UTC)

Yes, there was some sort of consensus to create a broader article about organofluorine chemistry/compounds, but not two. --Itub (talk) 06:21, 11 November 2008 (UTC)

I don't think "some sort of consensus" is what Wikipedia operates on. -Shootbamboo (talk) 22:59, 11 November 2008 (UTC)

Was there "any sort" of consensus to create two articles on essentially the same topic? --Itub (talk) 06:31, 12 November 2008 (UTC)

I started the organofluorines page on my own, you're right, but obviously I disagreed that they are essentially the same topic, because of the many contrasts between 5-fluorouracil (an organofluorine) and tetrafluoromethane (a fluorocarbon), for example. -Shootbamboo (talk) 00:53, 14 November 2008 (UTC)

• I agree with merging the two into Organofluorine chemistry. The two essentially boil down to the same thing. If in the end some sections in this article become so big that they could warrant an own article then they can easily be split of, but for now I am afraid the two articles are going to tell a lot of duplicate information. --Dirk Beetstra ^{T C} 11:09, 11 November 2008 (UTC)

Dirk, considering my recent edit to Talk:Fluorocarbon and my edits to the definition of Fluorocarbon, are you softening or willing to soften your stance that the organofluorine page is unnecessary? Thanks. -Shootbamboo (talk) 01:26, 12 November 2008 (UTC)

I take the suggestion below and I support the effort to merge in principle. In practice, it seems most wise to merge to the more general term, organofluorine. Thanks. -Shootbamboo (talk) 01:17, 13 November 2008 (UTC)

Organofluorine is not an acceptable name because it is an adjective (see article naming conventions and especially WP:ADJECTIVE). Given the flexibility of informal English grammar, some people may use organofluorine as a noun to mean organofluorine compound, as evidenced by the plural "organofluorines", but besides looking too informal and being less common (50 Google books hits for "organofluorines" vs 601 for "organofluorine compounds"), the use of organofluorine as a noun would not be more general in any way. Finally, organofluorine chemistry could be taken to be the most general term. One can say "Organofluorine chemistry is the study of organofluorine compounds. Organofluorine compounds are ... [insert rest of article here]" --Itub (talk) 06:48, 13 November 2008 (UTC)

Since this naming decision also applies to many other articles, I started a thread at http://en.wikipedia.org/wiki/Wikipedia_talk:WikiProject_Chemistry#Naming_consistency_for_organo__________chemistry.2Fcompounds . --Itub (talk) 17:44, 13 November 2008 (UTC)

The term organofluorine compounds is more inclusive than the term organofluorine chemistry (IMHO). For example, some organofluorines might not be welcome in an organofluorine chemistry page, as perfluorodecanoic acid has "no significant commercial uses, according to a fluorochemicals consultant."[1] I see the danger of future unproductive discussions/debates, if not for current editors, than future ones, over the definition of organofluorine chemistry. By contrast, we can all agree on the definition of an organofluorine compound (C-F bond containing molecule). All angles of organofluorine chemistry would be welcomed in an organoflorine compounds page. In the spirit of merging, we should pick the most inclusive term. Thanks. -Shootbamboo (talk) 00:53, 14 November 2008 (UTC)

I do not oppose merging in principle. Right now, I oppose it in practice, because I am completely reworking the organofluorine page. We will see what it looks like after I am done. Thanks. -Shootbamboo (talk) 00:28, 23 November 2008 (UTC)

That being said, I am going to remove the merge template propsals. -Shootbamboo (talk) 03:28, 23 November 2008 (UTC)

Merge tag (Fluorocarbon)

I disagree with this proposal as there is now a consensus on the page for the IUPAC definition. The "misplaced" content currently named as fluorocarbon derivatives should be moved to a page named polyfluorochemicals or polyfluorinated compounds, as has been proposed on Talk:Fluorocarbon (IMHO). There should be a place for poly-fluorinated chemicals that behave like fluorocarbons, due to the carbon-fluorine bond, but are not true fluorocarbons (outside of the organofluorine chemistry page). Right now, the organofluorine page says there are Fluorocarbons, Pharm&Ag, and the mono-fluorinated natural chemicals. Obviously, we are missing a class of poly-fluorinated compounds. These compounds represent a class of chemicals that are of interest to many, including myself. (See references to them as perfluorocarbon derivatives in the perfluorocarbon page). Therefore, I think a better place exists than the organofluorine chemistry article. Thanks. -Shootbamboo (talk) 02:57, 12 November 2008 (UTC)

I just added a {{contradict}} to the article. Large parts are not in its place in that article, but better in organofluorine chemistry at the moment, as is the synthesis section in that article. There may be a bit left over about compounds that only contain C and F, which could be enough for an own article (although also there large parts will be covered in other articles, e.g. fluorous biphasic chemistry etc.). Some cleanup is needed here. Also here I would suggest, merge, let this article grow, and see if there are parts which can split off as own articles (and for that Fluorocarbon may be one good candidate). --Dirk Beetstra ^{T C} 15:53, 12 November 2008 (UTC)

If we can agree on the term organofluorine compounds I withdraw my comment directly above, where I voice my concerns on the diversity of the physical, chemical, and biological properties of organofluorines. Thanks. -Shootbamboo (talk) 00:53, 14 November 2008 (UTC)

I withdraw my comments above. I have been reworking the fluorocarbon page. I think it has unnecessary content at the bottom, but I think it is a very useful article. The organofluorine chemistry page, however, is poorly written (see below). Merging, IMHO, is unwise at best. For comparison, contrast the poor quality of the organofluorine chemistry article with what I find as the high-quality Carbon–fluorine bond page. (Also newly minted.) As such, I am going to remove the merge proposal on the fluorocarbon page. -Shootbamboo (talk) 20:59, 22 November 2008 (UTC)

Quality of Article

Because this article is a spin on the old fluorocarbon article, produced quickly, there are quite a few sections written very poorly. Like this section: Hydrofluorocarbons Hydrofluorocarbons, compounds that contain only one or a few fluorine atoms, are the more common type of organofluorine compounds. Flurocarbons with few C-F bonds behave similarly to the parent hydrocarbons, but their reactivity can be altered significantly. For example, both uracil and 5-fluorouracil are colourless, high-melting crystalline solids, but the latter is a potent anti-cancer drug. The use of the C-F bond in pharmaceuticals is predicated on this altered reactivity.[1] Several drugs and agrichemicals contain only one fluorine center or one trifluoromethyl group. As you can see, there is a lot written that has nothing to do with hydrofluorocarbons. I wanted to make this obvious so my edits don't seem distasteful during a time of discussion/transition. Thanks. -Shootbamboo (talk) 19:19, 15 November 2008 (UTC)

Shootbamboo: I have been swamped in my real world so have been laying off of this thing for a while. I expanded the description of the chemistry aiming to help with the scope. Judging from the discussion on the WP-chem discussion page, the consensus seems to favor "organofluorine chemistry" as the main title. The problem with "organofluorines" is that it is jargon, a modified adjective. You are a remarkably active editor, but it does not appear that consensus has been achieve on the merge direction. My recollection is that we are pursuing Itub's proposal for three broad articles in this area: organofluorine chem (or similar name), fluorocarbon (merged with perfluorocarbons) and C-F bond (which appears to be in stable condition). In any case, I will probably be of only intermitant contact. Please continue to strive to be consultative widely and be patient.--Smokefoot (talk) 05:52, 23 November 2008 (UTC)

i am optimistic that we can be productive editors together. -Shootbamboo (talk) 06:34, 23 November 2008 (UTC)

Please try to be polite here, and avoid name-calling - this is invariably counterproductive. Let's limit the criticism to the content, keep the good work going and build camaraderie. Walkerma (talk) 03:04, 24 November 2008 (UTC)

Selective fluorination

My impression is that selective fluorination (in the sense of medicinal chemistry) is the biggest challenge/most topical/most important aspect in organofluorine chemistry. Can some chem folks put a rough % relevance to that aspect so we can have rough gauge as to how much this article should discuss selective fluorination? Thanks. -Shootbamboo (talk) 02:27, 28 December 2008 (UTC)

Organofluorine compounds in materials chemistry

Nice review I found by accident: Berger, Ricarda; Resnati, Giuseppe; Metrangolo, Pierangelo; Weber, Edwin; Hulliger, Jürg (2011). "Organic fluorine compounds: a great opportunity for enhanced materials properties". Chem. Soc. Rev. 40: 3496–3508. doi:10.1039/C0CS00221F..

Might have some good content for Organofluorine chemistry#Materials science. No time to add it myself now. Maybe in a few months. Or someone else interested. --Ben (talk) 16:53, 24 April 2012 (UTC)