Talk:Hydroamination

RLM0518 Peer Review

The introduction to the article is written in accessible language, and I believe is understandable to non-experts. However, the original introduction was only slightly expanded upon. While you don’t want to give much technical detail in the introduction, I might add a little more on exactly why this reaction is important and how advances in this synthetic process will be important for organic chemistry. Maybe give an example of a product that is produced industrially using hydroamination. The article is generally well-linked to the relevant more detailed articles on Wikipedia. I would suggest adding links to a few more sites such as “organic synthesis,” “amines,” “intramolecularly” (links to “intramolecular reactions”), “catalysts” and “heterocycles” (“heterocyclic compound”). I would also make sure to link the terms more related to physical chemistry such as “activation barrier” (“activation energy”), “entropy,” and “thermodynamically neutral” (maybe “reaction enthalpy”?). In general, my suggestion is just to make sure than a reader who wanted more information about a specific chemistry term could easily access it.

I believe the article needs some reformatting, not necessarily in terms of content but in terms of structure. There are a lot of details in the introduction sections which should really be in separate subheadings. What I suggest is to follow the introductory information (right now ending with, “…separate amine and unsaturated compound.”) with the Table of Contents. In this introductory section I would add a small figure – probably inline – that shows a very general overall reaction for hydroamination (maybe something similar to the top reaction in the first image on the current page). Then after the Table of Contents I might add a section that describes the reaction in general and perhaps includes something on its scope. In this section you might include the first two figures you added to the page (the order and content of the sections is up to you; this is just a suggestion). Those figures are clear and very informative, and I believe they would add nicely to the general explanation of the scope of the reaction. (If you wanted, you could also include a specific example of a hydroamination reaction demonstrating the “cool” chemistry it can accomplish – lots of examples in some of your reviews.) I would include all of the information on catalysis into the section on the Catalytic cycle (right now there is some information in the last paragraph of the introduction). Finally, I might suggest moving the section on thermodynamic versus kinetic products a little higher up in the article – it is more general than the base and group (IV) catalysis sections above it.

The general information included in the sections is appropriate both in length and content. The examples presented are appropriate and add to the text. My only suggested addition is adding a figure showing one example of a reaction mechanism catalyzed by a late transition metal.

The added figures themselves are of high quality and easy to read. I especially like the first one demonstrating the scope of intermolecular hydroamination reactions. However, I would suggest modifying the captions in most of the figures so that they are more able to stand alone from the text. For example, in the first figure I might say, “Examples demonstrating the scope of the hydroamination reaction.” I might clarify the catalytic cycle mechanism caption just by adding something like, “Proposed catalytic cycle for an intramolecular hydroamination reaction (T.J. Marks).” Just make sure to link the reference of this. In general, I suggest just making sure that the caption gives a clear description of exactly what is in the picture/scheme. For the section on thermodynamic and kinetic products I suggest adding a figure that shows the example reactions you are describing (the rhodium and palladium catalyzed reactions). Seeing the reactions would help the reader to more easily understand what you are describing. Finally, I believe either wrapping the text or making some of the figures thumbnails and putting them inline could improve the general presentation of the article. The reader can click on the picture to enlarge it. This would cut down on some of the breaks and white space in the article.

Yes, the references are complete – it seems that 11 were added (there were 9 references in the original article and 20 are included in the sandbox). Most are peer-reviewed journal articles or reviews, but there are also a number of textbooks/print resources. I believe there is a good range of types of references.

Overall, I believe the group did well in expanding the information available on hydroamination. They also did well in highlighting the unique and interesting chemistry that is possible with hydroamination. The figures they added help the reader to understand the scope of the reaction and one of the catalytic mechanisms by which it can occur. The major changes required include general reorganization of the article, some caption clarification, and some additional linking to existing Wikipedia articles. A few example figures would also enhance the article, but are not necessary for general clarity and understanding. In general, this group made a strong contribution the content currently in the “hydroamination” article. RLM0518 (talk) 02:07, 4 November 2013 (UTC)

CarboJoule Peer Review

Content

• The introduction is very clear and refers to plenty of sources. However, it could be more concise and the details could be discussed in the following sections.
• The introduction section makes almost half of the page. That's too much. It might be useful to split the introduction from the third paragraph to make a "general principal" section. Some sections, especially the "Base catalyzed hydroamination" one, could be more amplified, rather than only having two sentences and one graph.
• May add more eternal link for concepts like "heterocycle""nucleophile""chirality"... to make the content more accessible to non-experts.
• The exsamples are really representative and related to research, though most reference papers are ten years old. It's good for readers for having a figure for each section.
• The content is not duplicative and deserves a individual wiki page.
• Overall, the content could be more related to physical organic chemistry.

Figures

• The figures are well drawn. However, PDF is not a good format for pictures, which makes the details of the picture somewhat vague. PNG or even JPG will be much better.
• The figures are very informative and support the content well. Each figure is very representative and explains the
• Every single figure is good. Nonetheless, they are drawn in different scales, which makes the page look busy and disordered sometimes.

References

• The editor added 11 references, two of which are most recent papers. It's always good to see that the wiki page is up to date to the current research.
• The references are from journal/non-journal sources, so the readers can both see something from the textbook and something up to date at a time.

Overall Presentation

Overall, the editor did a great job. It has various reference sources, plenty of figures to help elucidate the concept. The editor shows his/her expertise in this field. However, the introduction section contains too much details. To split and create a new section may help. The figures are not in a unified scale, which makes the page look disordered. When introducing specific application and study, citation of more recent papers is always welcomed. The content could be more related to physical organic chemistry, e.g. kinetic study could be introduced for the catalyst part.

Additional Comments

UMChemProfessor (talk) 02:09, 5 November 2013 (UTC) The figures need work. Some are blurry in their current format and they are all different formats and sizes. The peer reviewers make some excellent points and suggestions.

Suggestions from ChemLibrarian (talk) 14:58, 5 November 2013 (UTC)

1. I see your images have a mixed file types (.png, .jpeg, .tiff and pdf). 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.
2. To adjust size and position of the images as other reviewers suggested, see this page Wikipedia:Picture tutorial

Response from the Authors

Thank you all for the suggestions. We considered and attempted to include most of the comments to make our article better.

Things we didn't change and why

Though we made most of the changes as suggested by the reviews there are a few things we did not change. We thought that the pictures being large and in the center was easier to read and more informative for anyone only browsing through the article vs on the side as thumbnails. This is especially true for the later sections as the figures are representative of the whole section. Against suggestions, we did not expand on the two sections that we did not create (5 Base catalyzed hydroamination and 6 Hydroamination catalyzed by group (IV) complexes). We felt that there was more important, more general information that was critical to the article such that we didn't alter these two very brief sections. At the same time, we didn't delete them as the information was correct, didn't negatively impacted the article, and finally, we felt it was easier to leave in than possibly having to deal with the previous contributors. As for the major review being rather old, there haven't been any very thorough and generally well received reviews on hydroamination in the past years such that the older was used as it still is in the literature. We felt that the article was related to this class as it is based around catalysis and contains a whole section about the thermodynamics and kinetics. We did add a sentence on how catalytic cycles are proposed/supported through use of physical organic principles.

Things we did change

To fix our article, we added links to other Wikipedia pages that you suggested, along with a few more that we thought were necessary. Also, we took the more detailed parts of the introduction section and moved the material into their own individual sections and expanded on them or added them to an existing section. We also added a section about the history of hydroamination after the introductory paragraph, along with another section Applications, which focuses on real world applications of the use of hydroamination in industrial chemicals and natural products as suggested. Both new sections included new figures. We also changed the format of the .pdf figures to .tif to make them much clearer. At first we attempted to use .svg format as suggested, but there were some issues with the images (as seen in the image below the wedged bonds are overlapping with the N, which occurs in the .svg file (as shown below) and not the chemdraw file or .tif file). Other oddities like this occurred with some of the other suggested formats. We ended up reverting to using the .tif as our format as it seems to have as many positives and negatives as the other acceptable options.

Markovnikov and Anti-Mark Addition

To make the figures that we added more unified we double checked that our figures were saved in the same format (.tif) with the same ChemDraw document settings (ACS) and even the same line width. We attempted to make the figures even more consistent by adjusting the size to try to get the bond lengths to look approximately the same length, though to get them all with the exact same length seems impossible. As suggested, we added more figures or improved the figures to make the text more clear. We hope you all like the corrections and the page. Thank you again for your help and commentary.