Tutorial

Scheme 1. How to navigate RateThisReaction.com.

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To take full advantage of the features of RateThisReaction.com, it is best to create an account and sign in each time you visit us. Features such as adding new reactions, reviewing reactions, and commenting on other people’s reviews are only available to registered users.

 

Creating an account is free and fast! During registration, you can either choose your own USER NAME or have one assigned to you. Your USER NAME will be displayed next to your reviews and comments. Your EMAIL ADDRESS will be part of your login credential. If possible, please use your school or work (company, government labs, etc.) EMAIL ADDRESS so that we can verify your identity in cases of irregular activities. An activation link will be sent to your email address.

Your personal information, including your full EMAIL ADDRESS and NAME, will not be shared with other users or visitors of this website under any circumstance. However, your POSITION, AFFILIATION, and the domain part of your EMAIL ADDRESS (i.e. the part after the @ symbol, e.g. @berkeley.edu) will be displayed next to your USER NAME.

To search for a reaction, you can search by the structure of the product or the reactant, the whole reaction, or the reference.

Searching by structure and searching by reaction currently support three structure editors:

  • VectorMol
  • ChemDraw browser plugin
  • Ketcher.

 

The ChemDraw plugin supports direct copy-and-paste from the ChemDraw desktop program, but requires having ChemDraw installed on the local computer as well as using the Firefox browser (Chrome discontinued support for NPAPI plugins, which is needed to run the ChemDraw plugin).

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To search by reaction, you can draw out the reaction scheme on the canvas by adding reactants and products. For each reaction participant you can choose the search type (exact search, substructure, or similarity), which allows for maximum flexibility. So more or less similar to Reaxys or Scifinder. When in doubt, go with the “Substructure”.

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To search by reference, you can type in the DOI number or the journal title/year/volume/page.

If you do not see the desired reaction, please sign in and add that reaction to the database.

To add a reaction, first please sign in.

On the page header, click “Add Reaction”, or at the bottom of the search result table, click “Reaction Not Found?”.

Once you are logged in, your search terms will be transferred to the “Add Reaction” page, so you don’t need to re-draw the structures.

On the following page, please draw the structure of the reactants and products on the left-hand side. That means, you do not need to specify all the reagents, which are defined as reaction components that are not incorporated in the product (e.g. a base for neutralization or deprotonation).

If you are adapting a literature procedure to your own substrate, please enter the actual substrates YOU used, not the ones used in the literature.

You can specify if a structure is the reactant or product by choosing “Add as Reactant” or “Add as Product”. If you want to modify a structure that is on the canvas, click that structure (which will load that structure to the editor), modify the structure, and click “Update” to save the change.

Pro Tips for ChemDraw:

  • Use Ctrl+Shift+K to clean up the structure and avoid weird bond angles and distances.
  • When entering a structure by typing the shorthand notation, such as “TMSCl”, right click on the structure and select “Expand Label”. Otherwise the website will not register it as a structure.

On the right-hand side is the journal information. We have a DOI-resolver that auto-fills the journal information from the DOI number. If the DOI-resolver cannot retrieve the reference information, or if a journal does not have a DOI number, please manually fill in the text boxes.

To review a reaction, click the “Review this Reaction” button below the reaction scheme.

First, please indicate whether you have followed the exact literature procedure, which includes (but is not limited to) same temperature, pressure, concentration, time, order of addition, stirring rate, workup methods, etc. The scale of the reaction can be different.

If you altered the reaction or workup conditions, no problem! Please just specify those changes, including (but not limited to) temperature, concentration, time, order of addition, atmosphere, etc.

If you are adapting a literature procedure to your own substrate, please enter the actual substrates YOU used, not the ones used in the literature.

With respect to the voting, if you did not follow the exact literature procedure, please think twice before giving negative reviews. The authors didn’t claim that reaction would work under a different set of conditions, right? However, if you altered the conditions and did not obtain the product or obtained the products in poor yields, please specify that in the comment section (as a warning to other users).

We ask you to rate the reaction based on 5 criteria: yield, ee (if applicable), ease of setup, ease of isolation, and availability of the reagents, all of which we believe are crucial to the broad adoption of a methodology.

In addition, we ask you to answer some simple yes/no questions to supplement the ratings. 

Finally, we encourage you to describe in words your experience with the reaction, or other details not covered by our five criteria. Please consider including details such as the scale of your reaction, noteworthy observations not mentioned in the paper (color, physical state, etc.), TLC of the crude product mixture, technical difficulties associated with scaling up, etc.

The full list of rating options is shown in the table below. Please note that the examples given to illustrate the difficulty levels of reaction set-up and product isolation do not cover every scenario. Please use your own judgement when rating the set-up and workup.  

 

1 star

2 star

3 star

4 star

5 star

Yield of (isolated) product:

Very poor: 0-20% of the reported yield

Poor: 20-40% of the reported yield

Modest: 40-60% of the reported yield

Good: 60-80% of the reported yield

Excellent: ±20% of the reported yield

ee (if applicable)

Very poor: Lower than 80% of the reported ee

Poor: 80-85% of the reported ee

Modest: 85-90% of the reported ee

Good: 90-95% of the reported ee

Excellent: ±5% of the reported ee.

reaction set-up

Very difficult: e.g. combination of multiple hazards and/or challenging techniques.

Difficult: e.g. involves highly hazardous materials (highly flammable, toxic, carcinogenic, explosive, etc.), and/or requires speciality equipment.

Advanced: e.g. requires proper Schlenk technique, or rigorously purified reagents.

Moderate: e.g. requires extreme temperatures (high and low), slow additions, or sequential additions.

Easy: e.g. simply mixing reagents (in a glovebox if air or moisture sensitive).

workup and isolation

Very difficult: combination of multiple challenging isolation techniques, e.g. fractional distillation of air- and moisture-sensitive products, or column under argon at -80 °C.

Difficult: e.g. Aqueous/organic extraction of air-sensitive products, or fractional distillation.

Advanced: e.g. somewhat challenging column, simple distillation, or filtering air/moisture sensitive products.  

Moderate: e.g. aqueous/organic extraction, recrystallization, or simple column.

Easy: e.g. product obtained by filtration and/or by evaporation of the volatile materials.

availability of reagents and catalysts

Very rare: very difficult to obtain; availability of the materials is seriously hampering the broad adoption of the method.

Rare: can be obtained through lengthy or challenging synthesis.

Intermediate: can be synthesized from common materials.

Common: commercially available but expensive (> $10/g for reagents, >$100/g for catalysts).

Commercial: available from common vendors and inexpensive.

 

Note on YIELD: If you did not isolate the product, please leave the “isolation” at “N/A”, and indicate in the comment that your yield refers to the crude yield.

We realize that it may take you a while to run the reaction before coming back to post a review, so we got you covered! If you click “Remind Me Later”, we will send you a reminder email in three days.

Please only review reactions that are published in peer-reviewed journals and that you have personally conducted. You can only submit one review for each reaction, but you can make unlimited modifications to your review. You may not, however, delete your reviews.

Please keep the reviews honest, objective, reasonable, and professional. Use more “I” statements, such as “I did not obtain the expected product”, which are irrefutable, instead of “you/they” statements, such as “their procedure is a joke”. Refrain from using “definitive” language, such as “always”, “never”, etc.

Please rate the five categories (yield, ee, set-up, isolation, and availability) independently. A reaction published in a highly regarded journal could involve a complicated isolation procedure and receive a low rating on “ease of isolation”, but this is the intended purpose of this website: to inform users how reliable AND how easy a reaction is. Having a low rating on “isolation” does not make a reaction “bad”. It’s just a challenging reaction to run.

If your own paper or reaction received a low rating, please do not jump to the conclusion that the reviewer is being dishonest or incompetent. Mistakes happen, and if your procedure is truly robust, over time, its average rating will reflect that.

Finally, please remember that RateThisReaction.com is designed to allow researchers to share their experience on chemical reactions and help each other troubleshoot. This website is not intended to engage people in personal or research group feuds. We reserve the right to suspend or ban users who behave unacceptably.

While we actively, to our best effort, monitor the content of this website, we do not guarantee the accuracy of the reaction schemes and the objectivity of the reviews and comments. In addition, we do not assume responsibility for any consequence of following a “tip” offered in reviews and comments. When in doubt, please always refer to the original literature and submit your own reviews. Use proper judgement and familiarize yourself with the hazards associated with the chemicals and techniques involved in a reaction.

In addition, we realize that the examples given to illustrate the difficulty levels of reaction set-up and product isolation do not cover every scenario. Please use your own judgement when rating a reaction.

Feel free to contact us about your concerns.

All contents, including but not limited to reaction schemes, user reviews, comments, etc. are properties of RateThisReaction.com and may not be reproduced without express permission of RateThisReaction.com.

Post a review today and be heard! Happy voting!

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