tool sheet - elsevier
TRANSCRIPT
Elsevier R&D Solutions
®
Tool SheetExploring a chemical reaction
Tool Sheet
Exploring a chemical reactionUse Ask Reaxys to explore reactions, substances and concepts
Learning objectives• Use Ask Reaxys as an entry point to browse content• Recognize how different interpretations of a query lead to
different results• Understand differences between record types• Use Filters to limit results
Search questionEsterification of benzoic acid was an example today in lecture for an acid catalyzed reaction with alcohols. What else can I learn about esterification?
Tool Sheet
1. A good place to start is to search a phrase using Ask Reaxys.
Ask Reaxys interprets the phrase in different ways and delivers corresponding result sets.
You can always see these interpretations by clicking Show Query in the breadcrumb trail bar.
The first interpretation recognizes “esterification” as a concept and “benzoic acid” as a compound and links the terms together with the preposition “of” to deliver reaction records.
The second interpretation ignores the preposition “of” and retrieves bibliographic records containing the keywords “esterification” and “benzoic acid.”
The breadcrumb trail at the top of the screen tracks activity during a session, laying out a means to navigate back to performed searches or result sets.
Tool Sheet
2. 86 reaction records are retrieved. The first reaction is with benzyl alcohol.
3. Filters classify the resulting records according to relevant categories.The Reagent/Catalyst filter shows the number of records reporting the use of specific substances as a catalyst.
Critical thinkingThe majority of hit reaction records use triphenylphosphine and diethylazodicarboxylate, and not the acid catalysts mentioned in lecture. What are these substances?
Reaction details such as yield, reagents, solvent and time are excerpted from the listed citations for easy comparison.
Each record lists citations with the target reaction.
Clicking each structure gives substance identification data and links to its substance record.
Tool Sheet
4. Use Ask Reaxys to learn more about each substance.
5. Ask Reaxys recognizes the word as a compound and delivers 14 substance records.
Critical thinking14 records for 1 substance? Ask Reaxys performs an exact search and delivers information on salts, isotopes, stereoisomers, mixtures and radicals of a substance.
Each substance record is linked to corresponding property data, as well as references to the uses or applications of the substance.
The first three substances listed differ in the way authors described the stereochemistry about the N=N bond.
Tool Sheet
Filters show that the majority of records include triphenylphosphine as a reagent or catalyst.
6. Limit the retrieved records to those that include triphenylphosphine.
Critical thinkingWith so many records listing these two specific reagents, these might be involved in a specific reaction.
Tool Sheet
Reaxys also indexes “Named Reactions” in the Reaction Type field. Many here are named Mitsunobu.
Critical thinkingThe Mitsunobu reaction must be a chemical transformation that can result in the esterification of an acid. What other information is there on Mitsunobu reactions?
7. Perform another search in Ask Reaxys.
Tool Sheet
8. Scan briefly through the first few of the 179,643 reactions retrieved.
Critical thinkingSome records involve esterification, but others involve formation of epoxides and amides. Mitsunobu reactions are quite general.
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REAXYS is a trademark of Reed Elsevier Properties SA, used under license. Copyright© 2015. All rights reserved. September 2015