Talk:Cyclohexane conformation

message: This page needs some editing in relation to conformational changes. What is there is very crude, and there is no reference to the calculation used to get the energy values of the various conformations. It's nice to see the use of the IUPAC definition of the half chair (four coplanar atoms). 
Hansonrstolaf (talk) 00:14, 7 March 2011 (UTC)
thread_title:  Conformational Discussion 

message: no: Ring inversion does not occur in cyclohexanes only. Although the way the ring flip is written now it's not obvious. --Cubbi 02:37, 4 June 2007 (UTC)
thread_title:  Merge of [[ring flip]] 

message: I can't seem to find any discussion of A-values on wiki! This seems like the obvious place for it, sicne they're always calcuated for cyclohexane, but possibly merits its own page - any thoughts?? Seansheep (talk) 09:22, 14 March 2008 (UTC)
thread_title: A-values

message: I was quite shocked to see the conformations listed here.  There was "envelope" listed as a major conformation, but with no explanation of what it was.  I think it's someone's misinterpretation of this, the most common conformation for cyclopentanes, so I simply removed it.  I suppose that a half-chair cyclohexane looks quite similar to that.  Also, there was mixed use of "twist-boat" (which is what I have always heard and used) and "twist" (which I was unfamiliar with).  I am recommending that we follow the recommendations of the Nelson paper I've cited in the lede section, and use twist-boat throughout, so I made the appropriate changes.  Is this reasonable?  Did I miss something?  Walkerma (talk) 18:48, 8 August 2011 (UTC)
replies: text: nice paper! It's certainly a good idea to use it. I keep telling myself to some day put together a Cremer-Pople conformation space plot for this page, where all those conformations map to points on a sphere and make for awesome big-picture presentation. --Cubbi (talk) 19:35, 8 August 2011 (UTC)
replies: text: Yes, I was thinking that the page needs some nice graphics, but I'm lousy at such things! Walkerma (talk) 20:45, 8 August 2011 (UTC)
thread_title:  Naming of conformations, Nelson paper 

message: Compare the definition of cis and trans in paragraph 1 of this article's "Disubstituted cyclohexanes" section, as of today's date:
*"Substituents found on cyclohexane adopt cis and trans formations... Cis formation means that both substituents are found on the upper side of the 2 substituent placements on the carbon, while trans would mean that they were on opposing sides."
to the definition contained in a reliable source:
*cis, trans: Descriptors which show the relationship between two ligands [atoms, group] attached to separate atoms that are... contained in a ring. The two ligands [atoms, group] are said to be located cis to each other if they lie on the same side of a [reference] plane. If they are on opposite sides, their relative position is described as trans. The appropriate reference plane… [f]or a ring (the ring being in a conformation, real or assumed, without re-entrant angles at the two substituted atoms) it is the mean plane of the ring(s). … If there are more than two entities attached to the ring the use of cis and trans requires the definition of a reference substituent…"
See http://www.chem.qmul.ac.uk/iupac/stereo/BC.html#26. Le Prof  Leprof 7272 (talk) 20:05, 30 May 2014 (UTC)
thread_title: Compare decent source to section content

message: It would be most helpful to show both boat and chair conformations at the beginning.
There is a beautiful picture of the chair conformation, but we need a similar one of the boat conformation.  Can anyone supply it? CharlesHBennett (talk) 13:13, 22 November 2016 (UTC)
replies: text: Yes, even with long-ago academic qualifications in organic chemistry and in biology, I can't picture each of the conformations described. Even just a clearer key to accompany :File:Cyclohexane universe.png, naming each numbered conformation would be an improvement. — OwenBlacker (talk) 16:38, 15 May 2017 (UTC)
thread_title:  Intro -- show the boat and chair conformation in an easy-to-compare way 

message: Only some of the 5 numbers 1,2,3,4,5 are mentioned in Wikipedia text. Please mention all five. And explain E=Energy unless already explained.
91.155.24.127 (talk) 09:48, 21 September 2017 (UTC)
thread_title:  "Interconversions between conformations" Image 

message: I removed all dispute tags, and I generally dumbed down the article to keep it (fairly) factual and uncomplicated.  If others think that my revision was too drastic, then revert my work.--Smokefoot (talk) 01:33, 20 November 2019 (UTC)
replies: text: The article mentioned the plausible "The polarity of substituent can influences their axial vs equatorial preferences. cis-Cyclohexane-1,3-diol prefers diaxial conformation, which allows formation of intramolecular hydrogen bond." But doi:10.1016/S0277-5387(02)00934-8 indicates that cis-Cyclohexane-1,3-diol crystallizes as the diequatorial conformer.  So at minimum, the situation is complex.--Smokefoot (talk) 13:17, 20 November 2019 (UTC)
replies: text: doi:10.1039/P29930001061 discusses the 1,3-diol in various solvents: "Values for ΔG° range from 0.1 kcal mol–1 in CCl4 to 2.7 kcal mol–1 in aqueous solution in favour of the conformation in which both hydroxy groups are equatorial." So intramolecular H-bonding (and solvent effects on it) do seem to have an effect on relative conformational stability. But not enough to overcome the ordinary equatorial preference. I tweaked your DOI format to make it a hyperlink. DMacks (talk) 06:42, 21 November 2019 (UTC)
replies: text:  Thank you! I was wondering about the Keq and I guess inevitable that H-bonding solvents are a big factor. There are many other things about the article that would be worth expanding or explaining.  It would be nicely illustrative to show low T and RT H NMR spectra for C6H12. --Smokefoot (talk) 15:30, 21 November 2019 (UTC)

text: And doi:10.1021/jo051049w addresses trans-1,2-dihalocyclohexane stability in solution and gas-phase for the different halogens, and different solvents for difluoro in particular. DMacks (talk) 05:59, 22 November 2019 (UTC)
thread_title: Major revision

message: — Assignment last updated by Kcat3 (talk) 00:25, 17 November 2022 (UTC)
thread_title: Wiki Education assignment: Honors Organic Chemistry I