SciFinder Scholar – Practice Examples – Substances & Reactions

Substances cyclohexanol 1. Use the “Locate” feature to the substance called “cyclohexanol.”

Number of substances = ______

Look at what the record for this substance contains:

CAS Registry Number Synonyms (i.e., Naxol, Anol, etc.) Experimental properties Predicted properties Number of references to this substance STN Files (other databases with data on this substance)

Get References  References associated with … Preparation (all years) Spectral properties (all years) Properties (all years) Note: All other options only go back to 1966!!!

2. Search for substances that have the exact structure for cyclohexanol as O drawn on the left.

Number of substances = ______

Why so many substances?

Repeat the exact structure search, but put a check by the box for “Only return substances that are single components.”

Number of substances = ______

Why so many substances?

Find references for all 18O isotope-containing isomers.

Select substances  Tools  Keep substances = ______3. (a) Draw the substance shown on the left. Search for substances that:

Number of substances = ______

3. (b) Search for this substance using the MF = C11H18

Number of substances = ______[Yikes!]

Substructure Searching

4. (a) Draw the substance shown on the left. Search for substances that: have this “substructure” “ … that are single components”

Number of substances = ______S Cl

4. (b) Repeat the search but modify the structure by: “Locking out” the sulfur atom from further bonds Drawing a hydrogen atom as shown. H Number of substances = ______S Cl

Cl 5. Draw the substance shown on the left. Search for substances that: have this “substructure” Cl O “ … that are single components” Why are aromatic moieties found?  Perform “Analyze by Precision”. Look at … “Conventional Substructure” versus “Closely Associated Tautomers and Zwitterions”

 Perform “Analyze by Ring skeletons” Choose “Ring skeletons with atoms”

Cl 6. Do a substructure search chlorobenzene. What does SciFinder Scholar force you to do? Organometallic Substances – Analyze by Precision

1. Draw the desired structure or substructure 2. Run the search. 3. Analyze results by Precision. 4. Choose “Conventional structures” or “Conventional substructures”.

You may widen your search to include tautomers or zwitterions, but often you do not need to.

For example, draw two thioacetates attached to an iron atom, and do a substructure search on a more complex substance.

S S Fe

S S Do a substructure search and limit to substances that are single components.

Number of structures = ______

Analyze by Precision gives: “Conventional substructures” = ______

“Closely associated tautomers and zwitterions” = ______

Look at the kind of structures that are described by these two terms: “Conventional substructures” (best for most purposes) “Closely associated tautomers and zwitterions” “Loosely associated tautomers and zwitterions”

Analyze by Real-atom attachments

Analyze the above structure (limited to “conventional substructures) … by Real-atom attachments. You can limit by atoms or by groups such as: A – any (not H) Q – any (not C, H) Cb – any carbocycle Cy – any cycle Ak – any alkyl chain X – any halogen M – any metal Click on the methyl group to see what substances have nitrogen attached at that carbon. Reaction Searching

Get reactions where the structures are “variable only at the specified positions.”

N

S N S S

S Product

Note that the earliest reaction that is found is from 1985. But this is “Antabuse” – a drug that is used to treat people who want to quit drinking (it makes you feel nauseous if you ingest alcohol. It has been used for many years before 1985.

Click on the drawn substance Antabuse in one of the reactions. Choose References  References associated with “Preparation”.

Number of references = ______

Year of earliest preparation = ______

Get reactions where the structures are “substructures of more complex structures.”

N

S N S S

S Product

Number of reactions = ______More Reaction Searching & Substructure Searching

Draw bipyridine. Label it as a product. To do an exact search for reactions in which this is a product, click on get reactions where this structure is “substructure of more complex structures”.

N N product Number of reactions = ______

Repeat the search, but limit to those in which the bond between the rings is formed.

N N product Number of reactions = ______

Refine these reactions to just those that involve tin by: 1. Select “Refine by Reaction structure” 2. Draw the following pyridine / tin substructure and label as “reactant or reagent”

N Sn Reactant/Reagent

3. Get reactions where the structures are substructures of more complex structures

It is not necessary to have the bipyridine structure in the “Refine by Reaction structure” search. However, a substructure search is necessary to find substances which contain Sn.

Number of reactions = ______

Analyze these reactions “by catalyst”. What catalysts are used most often? ______