User talk:Physorgchem13/sandbox

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)

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General Remarks/Overall Presentation: I believe that you greatly improved the content of this article. The sections and subsections were organized in a coherent manner and, for the most part, were written using clear language. Both the figures and the examples enhance the article. The references came from a variety of sources. Most of my recommendations are relatively trivial and are listed in the following sections.

Content: In the Talk section of the original article, someone recommended using http://www.scripps.edu/baran/images/grpmtgpdf/Krawczuk_Nov_05.pdf to introduce the topic. This is one of the resources I used when preparing for this peer review and I found it to be an excellent primer. Your introduction might benefit from adopting some aspects of it, such as the first two figures in which they directly compare alkyl substituted cyclohexanes and alkyl substituted tetrahydropyrans.

The section on Synthetic Applications was a mere three sentences long. If I were you, I would either expand it or eliminate it. Otherwise, the sections were of an appropriate length.

I am sure there are some places in the “Influences on Anomeric Effect” where you could link to other topics on Wikipedia. There are currently no links.

I have two specific editing recommendations: First, in the heteroatom hyperconjugation section, you switch your syntax around when referring to the different types of conformations. At first, you refer to the “"trans", "trans"” conformation and the “"gauche", "gauche"” conformation. However, later in the section, you refer to it as the “trans,trans” conformation. I personally prefer the italicized version, but whichever one you choose, you need to be consistent. Also, I also might advise against using the Cy, THF, etc. abbreviations. If someone was only interested in reading the section on Solvent Effects, for example, they would not understand those abbreviations because they were introduced in the Substituent Effect section. It does not take too much effort to write out the words in full and doing so could save a great deal of confusion for a potential reader.

Figures: In the introduction, it might be worthwhile to have a figure explicitly labeling the anomeric carbon; currently, you say that it is C-1 but the general audience may not necessarily know what that means. In addition, I understood the concept you were trying to convey with your description of C-Y-C-X, however, I think it could be made even better by labeling on the figure which atoms are Y and which are X. This could be as simple as using an arrow to point to them. The current figure in the introduction seems a little fuzzy. Did you upload it as a .png file or a .jpg? I personally found that the file type made a difference in the clarity. The rest of the figures were crystal clear.

References: The original Wikipedia page on the Anomeric Effect had eight references. Your sandbox has 15. I did not go through and check if you had in fact added eight references and just eliminated some of the original references. If you haven’t added eight, you will want to do so. You had a good mixture of different kinds of sources: there were journal articles, an encyclopedia article, and books.

P org 2013 (talk) 19:11, 2 November 2013 (UTC)

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Content: There were some strong sections added and also a few that need a little work. The introduction was actually rather confusing. Considering the majority of the audience looking at this page will be upper lever chemists, they could figure it out, but I think it would be better and easier to just clarify a few things. I do find the last paragraph in the introduction to be rather confusing. I believe there are a few typos that made it confusing (steroids vs sterics, hydroxytetrahydrofuranose (I’m no sugar chemist, but I think the name is incorrect), and cyclohexanol (it’s not an alcohol)). I think if you are leaving the part about glucopyranose on the page you need pictures. The figure that was on the original page is clear so there really is no reason to remove it. It’s also much easier to look at the picture instead of trying to visualize it based on the provided description. In the heteroatom hyperconjugation section, I got rather confused again. I would just call the two structure in the figure trans and gauche though they are listed as trans, trans and gauche, gauche. This may be due to my own ignorance, but I didn’t think you could label a single bond more than one of these. If this confusion is due to my ignorance, it would be helpful to more clearly discuss these for the general chemist. Another part that I came to that I find unclear was the Solvent Effect section particularly the part about axial positions and electrostatic interactions. I tried to access the provided reference, though I am unable to as I am currently not on campus. It occurred to me that another concept could explain the items discussed in this section. To me, it seems like the equatorial position would have more interactions with the polar solvent and thus be more stabilizing due to dipole-dipole interactions. The final section that may need some work is the Reverse Anomeric Effect. The second sentence was rather confusing; it would be best to include a picture here or just utilize better naming. The sections are of good length except for the last part about synthetic applications. Only one is listed, though it says there are many applications in sugar chemistry. Maybe list a few others or don’t say there are many? It also would be nice to link to solvent effects in that section since it was only a brief explanation. Generally, the examples given are fine. I’m assuming other than the content that was originally on the page that most information was produced for the project since anomeric effect is a pretty unique topic.

Small grammatical issues that would really shine up this page:(1) Influences on the Anomeric Effect- sentence 1, effected to “affected”.(2) Solvent Effect- sentence 1, One often brought up problem to “One common problem”. (3) Solvent Effect- sentence 7, there is more electrostatic repulsions to ...”there are more”…

Figures: Overall, the figures are nice. They are accurate and clear enough to read (the first is a lot less clear than the others for some reason) and help clarify the text. I think it would be helpful to label them (ie: E vs Z, gauche conformation, the names of the molecules in the intro). The labeling would make it easier for people.

References: There appears to be enough references with a mix of journals and books. Surprisingly, some references were deleted from the original page and I can’t really see what content that was deleted. It appears most of the original content was retained with only some rewording.

Overall Presentation: Overall, I think the page is rather informative. The last paragraph in Introduction needs some work. There certainly needs to be more referencing (especially dipole minimization and overcoming the anomeric effect as there are currently no references for either section). The pictures are well drawn and easy to read. It would be helpful to label them. In general, the page would be helpful for anyone looking to learn a little more about the anomeric effect.

--5402013SD (talk) 15:26, 3 November 2013 (UTC)

Suggestions from ChemLibrarian (talk) 02:26, 5 November 2013 (UTC)

1. As other reviewers suggested, if you have deleted references cited in the original article but kept the original sentences, please add those references back.

2. At the end of the first paragraph under the Physical Explanation and Controversy section, you linked to a blog page to the word "settle". I would suggest making this webpage a reference for the whole sentence instead of a link to one word "settle". If you concern is not to cite a non-scholarly source, I think it's OK. The blog you are citing is a professional blog and you have enough other scholarly sources throughout the article.

3.I see your images have a mixed file types (.png, .tiff, and .jpeg). Actually, Wikipedia recommends "The basic choices are SVG for simple diagrams (especially those that need to be scaled), JPEG for photographic images, and PNG for everything else" as discussed on this page Wikipedia:Preparing images for upload. So, if you drew these diagrams in ChemDraw, it's better to save them as .png . If you are using other tools allowing saving as .svg, that would be the best.

Additional Comments

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)

Response to Reviewers

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)