Talk:Carbon–carbon bond

Requested move

The following discussion is an archived discussion of a requested move. Please do not modify it. Subsequent comments should be made in a new section on the talk page. No further edits should be made to this section.

The result of the move request was: on hold per the arbcomm moratorium on hyphen–dash-related moves. I note the overwhelming consensus here is that the move should happen and is in line with the relevant style guides. ErikHaugen (talk | contribs) 18:51, 17 May 2011 (UTC) moved per consensus here and the relevant section of the MOS. ErikHaugen (talk | contribs) 16:42, 25 July 2011 (UTC)

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Carbon-carbon bond → Carbon–carbon bond – ACS Style Guide (3rd ed (2006), p. 267) states "indicate bonds by en dashes", giving "the C–C–C angle" as an example. –CWenger (^ • @) 17:24, 30 April 2011 (UTC)

• Carbon-hydrogen bond → Carbon–hydrogen bond
• Carbon-nitrogen bond → Carbon–nitrogen bond
• Carbon-oxygen bond → Carbon–oxygen bond
• Metal-ligand multiple bond → Metal–ligand multiple bond

• Support – per MOS:ENDASH and the ACS style guide example "carbon–oxygen bond". Dicklyon (talk) 17:37, 30 April 2011 (UTC)
• Strongly oppose; C–C-C is a symbol; if, as in isobutane, the carbon were linked to four carbons, it would be a two-dimensional symbol. A mere glance at the literature will show that carbon-carbon with a hyphen is normal usage; for those who believe that our much-contested Manual of Style should decide these things, WP:HYPHEN 3 says that compound modifiers should have hyphens. The idea that we should follow the advice of isolated style guides against usage is harmful to the encyclopedia. Septentrionalis PMAnderson 17:42, 30 April 2011 (UTC)

Your "symbol" argument was pre-refuted by the quoted "carbon–oxygen bond" example above, from the American Chemical Society's style guide; it agrees with our consensus style in MOS:ENDASH. The fact that many reliable sources do not observe such a typographical style is not a reason to abandon our principle of adopting best-practices style. Dicklyon (talk) 17:47, 30 April 2011 (UTC)

Yes, of course, I should have realized: "Everything Dicklyon says is right." The distinction between a word, a symbol, and a diagram is refuted [sic] by a sentence which mentions none of them; the vehemently and persistently disputed WP:ENDASH is consensus because a handful of revert warriors like it; and best-practice is whatever Dicklyon prefers. Septentrionalis PMAnderson 17:56, 30 April 2011 (UTC)

While I do have some biased sympathy for the idea that "Everything Dicklyon says is right," it would be better to focus on the issue than on the editor, per WP:NPA. Let me know if the linked snippet to the example didn't work for you, or if you just didn't bother looking. Dicklyon (talk) 18:50, 30 April 2011 (UTC)

WP:HYPHEN also makes a clear exception: "In some cases, like diode–transistor logic, the independent status of the linked elements requires an en dash instead of a hyphen. See En dashes below." Also the ACS Style Guide is very definitive in chemistry, not an "isolated style guide". –CWenger (^ • @) 17:50, 30 April 2011 (UTC)

This last sentence is an actual argument; demonstrate that chemists actually and generally do follow it in this regard, and I will support the move. Septentrionalis PMAnderson 17:57, 30 April 2011 (UTC)

It was not OK when I said it, but now it is? OK, good enough. Dicklyon (talk) 18:48, 30 April 2011 (UTC)

Both mentions were incomplete; CWenger appears to realize this. Septentrionalis PMAnderson 22:01, 30 April 2011 (UTC)

I am not sure what I realize... –CWenger (^ • @) 22:18, 30 April 2011 (UTC)

The ACS Style Guide is the official standard to be used by anyone writing an article in an ACS-published journal...a built-in pool of actual uses not just an independent statement of a standard to use at will. Just for fun, I searched for "carbon carbon bond" in titles of all ACS articles this year: 6 use en-dash, 1 uses hyphen. DMacks (talk) 18:35, 30 April 2011 (UTC)

Then it is ignored a significant percentage of the time, even in ACS journals. What does everybody else do? Septentrionalis PMAnderson 22:01, 30 April 2011 (UTC)

"Everybody else" does whatever they do. Are you saying we should follow them instead of following the best practices as written down in our manual of style, and that of the American Chemical Society? As I stipulated above, a majority of sources don't pay much attention to nice typography, and just use hyphens where en dashes would be more appropriate. So you want us to do the same? Dicklyon (talk) 22:56, 30 April 2011 (UTC)

Shorter Dicklyon: "Most people don't do what I want; but what I want is best practice; so everybody should do what I want."

No. This encyclopedia is written in English, not French; we have no Academy to decide what English is, merely the consensus of anglophones. Even the Académie française is forty writers with actual credentials, not one self-appointed Wikipedian. Septentrionalis PMAnderson 23:16, 30 April 2011 (UTC)

Do feel free to answer: What does everybody else do? That approach, unlike the demand above to ignore the evidence, will convince me if the necessary facts can be shown. Septentrionalis PMAnderson 23:23, 30 April 2011 (UTC)

What percentage of scholarly papers using en dash in "carbon–carbon bond" would it take to make you realize that it's acceptable in normal usage? It looks like it might be an actual majority in books (based on the first two pages of Google books hits, not counting the works that were done on a typewriter or the one that's a wiki mirror but uses no dashes at all). And then there are the amusing ones like this book, where they don't seem to know how to make en dashes or hyphens, so they use em dash for everything! Dicklyon (talk) 23:36, 30 April 2011 (UTC)

What was the basis of your opposition again? You haven't looked at the usage, but you just can't stand the MOS? Dicklyon (talk) 23:57, 30 April 2011 (UTC)

No, I have looked at the usage, and dashes are rare; not as rare as in other cases, but rare. What I object to is the all too prevalent practice of supporting something which neither MOS nor usage support and claiming MOS requires whatever fantasy Dicklyon would like. Septentrionalis PMAnderson 03:16, 1 May 2011 (UTC)

Doesn't MOS:ENDASH #2 and/or #3 support this move? –CWenger (^ • @) 03:21, 1 May 2011 (UTC)

Both of them are vague, which is the besetting problem with the whole section; that both of them are disputed is too obvious to need mention. 2 almost certainly does not; this is not a carbon versus carbon bond, is it? 3 is more arguable, but differs in this: in Michelson–Morley, the dash offers a differentiation of meaning. Here it does not; using the dash communicates nothing but the typographical vanity of the author. Septentrionalis PMAnderson 03:35, 1 May 2011 (UTC)

I don't know where you're looking if you think they're rare; your "mere glance at the literature" link above has 4 books with dashes among the 8 books found on the first page (I'm not counting the one that goes to a wrong irrelevant book with no carbon-carbon in it, nor the one that is a wikimirror). Do keep in mind that Google's OCR will render them as hyphens, so you have to look at the book or paper in question to see the typography. And the guidelines are plenty clear for most people; the "carbon–oxygen bond" even appears explicitly as an example of the guideline "two-word concepts where both words are of equal weight" in the ACS guidelines, which is a lot like our "To stand for and between independent elements." And I agree that guideline 2 would be better if it also included the "between" relation explicitly along with "versus" and "to", but now you'll just have to settle for "carbon-to-carbon" to fit that usage example. Dicklyon (talk) 03:49, 1 May 2011 (UTC)

I think MOS:ENDASH #2 is more applicable, as I would say "to" is the most suitable replacement for the punctuation between "carbon" and "carbon". I can't say it has any clarifying effect that I know of, but as a minor point, people often use equal signs to denote double bonds (=), so it makes sense for the single bond symbol to be the same length, which is the en dash (–), not the hyphen (-). –CWenger (^ • @) 03:54, 1 May 2011 (UTC)

(left) Cwenger makes two points:

• One illustrates what I mean by calling WP:DASH vague: it says that a dash can be used to represent to, but illustrates that by 4–3 game; a game with a score of 4 points to 3 is a different sense than a bond of carbon to carbon.
• On the other I agree that the symbol should be C–C–C and C–C=C, as it is; but does anybody write carbon=carbon bond for a double bond and expect to be understood? especially by the lay audience for which we should be writing? Septentrionalis PMAnderson 20:14, 1 May 2011 (UTC)

No, nobody does that. Such symbols are quite outside the scope of normal English punctuation and typography; not clear why CWenger gave you that to muddy the waters with. As for WP:DASH being vague, one could easily add more examples of normal en-dash usage if you'd allow it. So are ready now to withdraw your "oppose" and let this move along? Dicklyon (talk) 20:45, 1 May 2011 (UTC)

Yeah, I regret presenting that rationale now. Although I have no idea why C~C would use different punctuation than carbon~carbon. –CWenger (^ • @) 20:55, 1 May 2011 (UTC)

Because it's a valid reason for the symbol to use an en dash, which it is. If he can come up with a reason for the phrase to be punctuated exactly like the symbol, that would be an actual reason for the move, a pleasant change from unverifiable claims about what all professional typographers do (unless this is a real typographer fallacy). They differ for the same reason one uses C and the other carbon; one is a miniature diagram, the other a word. Septentrionalis PMAnderson 20:59, 1 May 2011 (UTC)

• Support—professional typography, used elsewhere, carries meaning for readers (even those who don't explicitlly follow typographical niceties), consistent with WP's well-established practices; especially suitable for computer monitors. Tony (talk) 02:12, 1 May 2011 (UTC)
• Support. Suggested move follows both MOS:DASH and appears to follow the definitive style guide for this topic. Can't really see why this is being argued over to be honest... Jenks24 (talk) 03:13, 1 May 2011 (UTC)
• Move to close. Given the widespread support, and that the only objection is from an anti-MOS crusader who hates en dashes, who seems unwilling or unable to count uses in his own linked evidence, and has no other rationale for objecting, besides his personal dislike for me, apparently, I move we close this, do the move, and move on. Dicklyon (talk) 21:04, 1 May 2011 (UTC)
  • Please ignore this personal attack; that it describes as it does an objection founded on no evidence of majority usage or of advantage to the encyclopedia is characteristic of the tone of this discussion. Septentrionalis PMAnderson 21:09, 1 May 2011 (UTC)
• Support. Obvious. — kwami (talk) 21:10, 1 May 2011 (UTC)
• Support. looking at the first 2 pages of google books (in the link used by PMAnderson), I found about 40% usage for dash and 60% for hyphen. And, unlike other topics, there is one authoritative style guide for the whole field. Let's not import disputes from other Move Requests where the circumstances are different. --Enric Naval (talk) 10:48, 3 May 2011 (UTC)
  • That is certainly sufficient frequency for us to permit the dash; I still see no particular advantage to the move. (The dashes must be relatively low on that list.) I therefore strike strongly. Septentrionalis PMAnderson 16:45, 3 May 2011 (UTC)
• Support per Dicklyon. Ozob (talk) 10:52, 5 May 2011 (UTC)
• Support Rjwilmsi 18:39, 5 May 2011 (UTC)

The above discussion is preserved as an archive of a requested move. Please do not modify it. Subsequent comments should be made in a new section on this talk page. No further edits should be made to this section.

Maybe a {{bond}} template and then a user preference for hyphen vs. n- vs. m- dash?!

I just skimmed the long and rancorous discussion regarding typography. Given that this is a wiki, perhaps someone could make a "{{bond}}" template. Then have a user preference for "For chemical bond-related language, I prefer: 1) "plebeian hyphens" 2) en-dashs 3) em-dashs" Jimw338 (talk) 06:43, 21 February 2019 (UTC)

I just noticed that the discussion started about redirects.. How *does* this work, given that the pages are accessed (at least by some software I assume) by ASCII? Jimw338 (talk) 06:45, 21 February 2019 (UTC)

New evidence for a carbon-carbon single electron bond

I'll leave this source here and wait if any other people want to insert it into the article or elaborate their opinion on this because I noticed that its is significant enough to be considered being included in textbooks. (poor future students).

Shimajiri, Takuya; Kawaguchi, Soki; Suzuki, Takanori; Ishigaki, Yusuke (2024). "Direct evidence for a carbon–carbon one-electron σ-bond". Nature. doi:10.1038/s41586-024-07965-1. PMID 39322667. ChopinChemist^Talk? 13:35, 1 October 2024 (UTC)