Talk:Anomeric effect

message: Hello, I am currently taking a class where one goal is to improve chemistry wikipedia pages for the general public. I will be editing this page over the course of the next month. I have read through the talk page and saw how passionate people are with this topic. My goal is to improve the page so more people will be able to understand anomeric effect and to provide more examples besides just the 6-member ring chair conformations. I am willing to take any other suggestions as to how to improve the page. Thank you! (Physorgchem13 (talk) 23:25, 21 October 2013 (UTC)
replies: text: A citation supporting the paragraph would suffice to bring it from "opinion" to "published opinion", and therefore make it notable enough to be included. DMacks 20:22, 30 May 2007 (UTC)

text: No, the statement in this article was wrong and I have corrected it. --Itub 13:25, 6 June 2007 (UTC)
thread_title: Untitled

message: User:Vgsbox has been adding his original research and opinion to this article again, which goes against Wikipedia policies. It is also obvious that he has a conflict of interest, because he is citing his own work and giving it undue weight. I'm reverting the latest edit for these reasons.
I'm not saying that the article is perfect, as it could certainly needs expansion. I'm not even saying that the "conventional" explanation for the anomeric effect is The Truth. However, we have to give more weight to the mainstream explanation according to Wikipedia policies. Also, according to the No Original Research policy, preference should be given to secondary and tertiary sources, which means that in this case it is preferable to cite reviews and monographs rather than original research articles. Original articles that have not been cited much in the secondary scientific literature, with theories that have not had enough discussion in the scientific community shouldn't be given as much weight as the reviews and monographs. If Box turns out to be correct, surely future reviews, monographs, and even textbooks will reflect that, and we should certainly update the Wikipedia article accordingly. But that has not happened yet, and Wikipedia is not a crystal ball, so I'm afraid we'll have to wait until that happens. --Itub 12:16, 13 June 2007 (UTC)
thread_title:  Original research and conflict of interest 

message: Six chair conformations for a 6-membered ring? You take one, do a chair-flip to get another, that's all I've ever heard of. Is the article conflating ring conformations with conformations of the side-chains on that ring? Let's please be very clear with terminology here even as there are certainly issues involving side-chain conformations that are based on the same/similar principles as ring-confs themselves. DMacks 14:13, 14 June 2007 (UTC)
replies: text: I think he is talking about rotation around the exocyclic C-O bond. You have 2 chair conformations and three rotamers around that bond, resulting in a total of 6. However, the argument he added is misleading for reasons that I'll add later when I have time... --Itub 14:30, 14 June 2007 (UTC)

text: Ok, I'm back. I will call the oxygens "endocyclic" and "exocyclic", which I think is more clear than O1 and O2. The issue is that the exocyclic C-O bond is free to rotate and can adopt three conformations. In two of those, the endocyclic C-O antibonding orbital can interact with a lone pair of the exocyclic oxygen, which is stabilizing according to the hyperconjugation model. But that has nothing to do with which of the two chair conformations is favored. Now, if you look at the endocyclic C-O bond, it has only two (rather than three) conformations available because of the constraint of being in a ring. Of these two conformations, only for the axial one can the exocyclic C-O antibonding orbital interact with a lone pair from the endocyclic oxygen. This is similar to the case of dimethoxymethane in that there are two generalized anomeric effect involved, one per each rotatable bond to an oxygen. But in the case of a sugar or similar molecule, when talking about the non-generalized anomeric effect (dealing only with axial vs equatorial), only one of these two matters. (This prose can be hard to parse, making a drawing or a model certainly helps...) --Itub 15:33, 14 June 2007 (UTC)

text: Yes, I certainly agree that there are two good chair conformations essentially independent of three exocyclic-bond rotations, and that only the former is relevant to the discussion. There are always lots of effects and many global conformations available obviously. But for the article here and as a teaching example (i.e., not research paper), I think it's best to discuss a single part well rather than only considering the whole picture. DMacks 16:37, 14 June 2007 (UTC)

text: No, what's relevant are the Wikipedia policies that you keep ignoring: WP:NOR and WP:NPA. --Itub 14:54, 20 June 2007 (UTC)
thread_title:  Chair conformations 

message: Obviously there are many issues with THPOH, at least in part because there are two anomeric-effect bonds to consider. The ring doesn't seem to simplify anything beyond dimethoxymethane, though it is probably a more common application for many readers. Maybe we should use a 2-haloTHP instead of 2-hydroxy: only one rotatable bond, so we can focus on the anomeric effect itself (dipole/dipole, hyperconjugation, other effects) without also having to consider complications from sidechain conformations, less important H-bonding to solvents, etc.? DMacks 16:46, 20 June 2007 (UTC)
thread_title:  Yet another idea 

message: I wonder if is this could be easier to understand if it were introduced kind of like in http://www.scripps.edu/chem/baran/images/grpmtgpdf/Krawczuk_Nov_05.pdf This may provide some insight on how to make this topic easier to understand. Sion55 (talk) 14:41, 25 July 2011 (UTC)
thread_title: Ease of reading

message: Overall, I think you did a great job making the introduction more accessible to non-experts compared to the original article. However, there are a few areas in the introduction that are slightly confusing. First, because you removed the pictures depicting glucopyranose, I would also remove the sentence that talks about glucopyranose. Another option is to re-include the picture and keep the description in because it was a nice example from the original article. If you do this, I think it would be more effective after you talk about the general case (C-Y-C-X). That way you can start more general and move to a more specific example. The example you use in your general case is slightly confusing. You define Y as a heteroatom, but then in your drawing on the left Y is a carbon, which is not a heteroatom. Perhaps state that the drawing on the left does not exhibit the anomeric effect, while the drawing on the right with a heteroatom, Y, exhibits the anomeric effect. Also, it would be helpful if you explained why the effect is most common when Y= oxygen. Lastly, for the introduction I think you wrote “steroids” instead of “sterics” (In the cyclohexanol molecule on the left, the substituent prefers the equatorial position due to steroids.) 
As you move into physical explanation and controversy there are some terms that could be defined to make the article more accessible to non-experts. A short sentence defining hyperconjugation would be helpful in addition to your link. Also, I suspect most non-experts will not know what antiperiplanar is or what a sigma* orbital is. A little more explanation would help clarify. The wording in your last paragraph for the hyperconjugation section is confusing. You can take out the two also’s and a few commas. It would be helpful if you explained what the inconsistency is between theory and experiments for acetal chemistry, instead of just stating that there is an inconsistency. A figure here might help clarify. For the section on dipole minimization, the example for the E/Z conformation of esters needs a reference. Lastly, the subsections are: Hyperconjugation, Dipole Minimization, then Hyperconjugation again. You can probably combine the two hyperconjugation sections. 
I thought the influences on anomeric effect was well done. The one thing I would suggest is linking to “reverse anomeric effect” in your own article instead of saying “see below”. I think there is a way you can link to sections within your own article. Also, a picture for the reverse anomeric effect would be very helpful for non-experts. 
Finally, I think the section on synthetic applications can be expanded. A picture depicting the Koenigs-Knorr Glycosidation and an explanation as to how the anomeric effect is applied in this case would help expand this section.
In general, I thought all of your examples were appropriate and not duplicative of any other content already on Wikipedia for the anomeric effect.  Your figures are very well done, easy to read, and informative. Additional explanation in the text for a few of the figures (like the C-Y-C-X example) would be helpful for non-experts.  You have a nice combination of journal sources and secondary sources, however, a source is missing for the example of the E/Z conformation of esters. 
--Iriidium (talk) 15:38, 2 November 2013 (UTC)
thread_title:  Peer review and responses during the educational assignment in Fall 2013 

message: There have already been an extensive number of comments on this page so I'll refrain from adding too much more. The peer reviewers advice is good and should be listened to. The figures are a mix of old and new, and that is OK, but the formatting is not consistent. It would be better if it was. You can either re-format your figures, or make modified versions of the old ones. UMChemProfessor (talk) 20:25, 5 November 2013 (UTC)
thread_title: Additional Comments

message: Thank you for all of your suggestions. We would like to comment on how we took your suggestions.
Citations:
If we deleted citations from the original page it means we deleted the information. If you read the talk page from the original page you would find that an individual cites his/her own research, which is against wiki’s policy. We found broader information from secondary sources to take its place. References were also added in to the E/Z conformation and the overcoming the anomeric effect sections. The external link which was from the original article, was fixed so it cites the sentence and not linked to the word. 
Figures:
We have adjusted our figures for all of them to be in the same format. Further more we took the suggestions of making our figures clearer by labeling within the figure. For example, the E/Z conformation figure and sigma star orbital figure were adjusted with labels. We also added a few more figures (reverse anomeric effect and natural products) and returned the intro figure to help facilitate our explanations.
Content:
In response to using the Baron group document we did use the document to start researching our topic and ended up finding more detailed information in other sources. We have edited the introduction to introduce our topic with clearer descriptions. For the C-Y-C-X explanation, we adjusted the figure and provided a more general description to aid the general publics understanding of it.  Furthermore, we have added definitions of concepts through out the article and adjusted any grammatical errors that were pointed out. The organization of the physical explanation section was redone to combine the hyperconjugation sections. The synthetic application section was expanded and more examples were provided, to address the concerns that the section was too short. More links were also added within the influences on anomeric effect section. As far as editing the trans, trans and gauche, gauche areas, details were added to the paragraph for further explanation. Any abbreviations were eliminated and full words were used to eliminate any confusion in the article. A figure was added to the reverse anomeric effect section to help clarify any confusion. In general, all of the information that was added to the article came from the references cited. The explanations were summaries of others work and not our own new explanations for the phenomena.  — Preceding unsigned comment added by Physorgchem13 (talk • contribs) 17:19, 9 November 2013 (UTC)
thread_title:  Response to Reviewers