WVU Chemical Literature Question

CHM 4060: Use of the Chemical LiteratureAssignment 11 (100 points)
Now that you know how to find chemicals, we’re going to discuss ways to actually dig into the
literature of them. Let’s start with the most important thing – how do we find how to make them?
There are several different ways…
Recall from our last assignment we had discussed how to look up acetone. If we search for it on
SciFinder, it returns a result that looks like this:
As it turns out, there are several ways to use this information. The first is by clicking the “Get
References” hyperlink. Doing that returns a window that looks like this:
First, notice that it says “All substances.” In this instance, there’s only one substance, but if you
have a list of chemicals, you can highlight any that you’re interested in looking at references for
at the same time by clicking on the box to the left of the CAS number in question. Second, you
can see that there are ways to limit the results here. For example, if we are only interested in
references that discuss the biological study of acetone, we could limit our search using that box.
But for purposes of this exercise, we’re going to limit our search to those that show the
preparation of acetone, so we click on the “Preparation” box, then click on “Get” to see all of the
references that contain how to synthesize acetone.
For Part 1 of your assignment this week, search for each of the compounds from last week’s
assignment (using whatever method necessary) using SciFinder, limit your search to those that
disclose their preparation, and take a screen grab of any of the results (you just need one) that
show a reference that synthesizes each of these compounds.
Another way of evaluating ways to prepare any compound on SciFinder is using the green
colored icon (which you can use directly from the individual chemical (right above the CAS
number) or using the “Get Reactions” hyperlink). When you click on that hyperlink for acetone,
it returns a query box that allows you to limit your results as follows:
This is especially handy if you’re looking to find what reactions the chemical of interest might
undergo (which, if you’re doing that, you should always choose “Reactant or reagent” – I really
have no idea why they distinguish them as two separate items). However, since we’re interested
in searching for reactions that show how to synthesize our compound, we would choose
“Product” and then hit “Get” to see results that look like this:
Obviously there are a bunch of ways to synthesize acetone! These results give you a hyperlink
directly to the article/patent for the result, and it’s quite useful to note that this method lets you
sort your results in a variety of ways (year, yield, number of steps, etc.).
For Part 2 of your assignment this week, search for each of the compounds from last week’s
assignment (using whatever method necessary) using SciFinder, look for reactions where the
compound is a product of the reaction, and take a screen grab for one of those choices where you
feel the product is formed in a high yield (or at least one you consider acceptable).
So that I don’t get accused of being a corporate shill for SciFinder, you can ALSO search for
some of this type of information using Reaxys. From the front page of Reaxys, you can search
for chemicals:
Note that you can search by name, CAS number, or by drawing the structure (by using the
“Draw” link). For example, searching for acetone by CAS number returns the following:
The first thing you should be thinking is “how are there 5 different substances with the same
CAS number?,” but don’t fret about that. If you click on the “View Results” tab for Substances,
you’ll see that most of those are transient species like acetone radical or acetone ion, but we’re
obviously interested in just acetone itself, and what you’ll notice in the results:
is that there’s a hyperlink for “Preparations,” which, if you click it, will give you references that
show the compound’s synthesis. Similar to SciFinder, you can sort these references in a lot of
ways, including by yield, publication year, etc.
For Part 3 of your assignment this week, search for each of the compounds from last week’s
assignment (using whatever method necessary) using Reaxys, look for results that show
Preparations, sort them by the highest yields, and take a screen grab of one of those results.
Compile all of your screen grabs in order and separated by parts onto a single document. Save it
as either a .doc file or a .pdf file, naming the file as:
FirstnameLastnameAssignment11.doc or FirstnameLastnameAssignment11.pdf
Part 1 (32.5 points)
13 screenshots of references
•
Part 2 (32.5 points)
+2.5 for each
screenshot of a
reference for a
molecule from
Assignment 10*
13 screenshots of references
•
Part 3 (32.5 points)
+2.5 for each
screenshot of a
reference for a
molecule from
Assignment 10*
11 screenshots of references
DO NOT HAVE TO INCLUDE:
• 7681-52-9
• 24937-16-14
• +2.5 for each
screenshot of a
reference for a
molecule from
Assignment 10*
Must demonstrate correct
search parameters
• -.5 If reference
doesn’t disclose
preparation
• -1 If search isn’t
through scifinder
Must demonstrate correct
search parameters
• -.5 If molecule isn’t a
product of the
reaction
• -.5 If molecule isn’t in
high yield
• -1 If search isn’t
through scifinder
Must demonstrate correct
search parameters
•
•
•
Total (100 points)
-.5 If reference
doesn’t disclose
preparation
-.5 If molecule isn’t in
high yield
-1 If search isn’t
through Reaxys
39 screenshots of references
+2.25 for each screenshot
+7.5 for completing
assignment
*The 13 screenshots for each part refer to the 13 molecules mentioned in Assignment 10’s Part
1, Part 2, and Part 3. You do not need to use your molecule from Part 4.