SciFinder: Reactions

How to use the world's largest chemical information database to find chemical references, compounds, and reactions.

Reactions

The Reaction database in SciFinder is a terrific resource, but ... remember it does not cover all reactions, not even those found in articles and patents in the Reference database. Coverage of pre-1985 reactions is spotty.

SciFinder Reaction is a relatively recent addition. The list below gives an idea of the coverage of reactions. Although SciFinder started adding reactions to the Reaction database in 1985 from journal articles, they did not add nearly as many reactions nor the amount of detail as they do today.

1985 - present       Journals indexed by Chemical Abstracts          
1991 - present Patents indexed by Chemical Abstracts
1974 - 1999 (articles);  1982 - 1999 (patents) VINITI (USSR) and ZIC (German) databases
1840 - 1985 Core Reactions Database (INPI, French database)
1971 - 1997 Biotransformations database
1921 - present Organic Reactions; Organic Syntheses; Encyclopedia of Reagents of Organic Synthesis

Summary -- SciFinder has added several reaction databases (VINITI, ZIC, Core Reaction Database, Organic Reactions, Organic Syntheses and EROS) to supplement its own reaction indexing that began in 1985 for articles and in 1991 for patents.

Image source: Acid-catalyzed addition-elimination mechanism.  Eschenmoser. Wikimedia Commons.  Public domain.

Non-Reaction Functional Groups

To find reactions in which a particular functional group survives the reaction condition add a non-functional group to a reaction search.

For example, you can search for the oxidation of an alcohol to a ketone in the presence of sulfide.

The "Choose a functional group" icon is located on the lower left of the reaction drawing editor. It has part of "alcohol, ketone, aldehyde" written on the icon. Simply choose the functional group in the reaction and label it "non-reacting".

Preparation Searches

Three ways to search for preparations.

  1. Explore substances.  Choose references for Preparation role. This is the best way.
  2. Explore references.  Type in "preparation of [insert the CAS Registry Number]. This is just as good.
  3. Explore reactions.  Use the reaction drawing window.

Thank You

Content from this page is from Auburn University's SciFinder LibGuide, by Bob Buchanan, who kindly gave us his permission to re-use it. 

Analyze and Refine

The Analyze and Refine tools are different in the reaction, substances, and references databases. Even within a database, the Analyze and Refine tools are often different ... although there is some overlap.

Analyze  

Author
Catalyst -- Useful tool
Company/organization
Document type
Experimental procedure -- Some SciFinder reactions include experimentals
Journal name
Language
Number of steps -- Often useful to limit to one-step
Product yield -- Use with caution
Publication year
Solvent -- Useful tool

Refine

Reactionl structure
Product yield
Number of steps – Often useful to limit to one-step
Reaction classification:
       Biotransformation
       Catalyzed
       Chemoselective
       Combinatorial
       Electrochemical
       Gas-phase
       Non-catalyzed
       Photochemical
       Radiochemical
       Regioselective
       Stereoselective
Excluding reaction classification
Non-participating functional group (217 from which to choose)

Image source: Combustion reaction of methane. Jynto, Robert A. Rohde, Jacek FH, Jynto.  CC BY-SA 3.0.

Ten Tips

There are more than ten things worth knowing about in the Reaction database,

but these ten tips are definitely worth keeping in mind.

Not included on this list is  information included in the other boxes on this page.


Group by Transformation Groups by general reaction type.
2 Group by Document Collapse the number of reactions that appear to one per paper.  Useful when reactions from a few publications dominate the list of reactions.
3 Sort by Experimental             Procedure Some reactions include detailed experimentals in the SciFinder record.
4 Solvent Consider restricting to solvents in which your substance(s) is soluble.
5

Number of Steps

Limit to one-step to avoid multi-step reaction schemes.
6 Lock Atoms Tool
Restrict substructure searches at specific atoms.   Lock ring fusion or formation tool  restricts the presence of rings.
7 Bond Making/Breaking Tool This can reduce the ambiguity of the drawn reaction.
8 Atom Mapping Tool
This can reduce the ambiguity of the drawn reaction.
9

Functional Group Tool

Insert an entire functional group into a search. This is especially valuable for including non-reacting functional groups.
10 Similar Reactions
Retrieve reactions that are similar to the drawn reaction.