The Literature of Organic Chemistry


Primary References

The primary literature consists of original documents which were published in scientific journals. These articles contain the actual reports of the scientists who performed the work. They are basically ultra-quality lab reports which have been reviewed by peer readers. These reviewers will critique the content and importance of the work before the editors of the journal decide whether to print the article.

The primary literature also contains reviews by experts in their fields. For instance, an organic chemist may outline all that has been done regarding the reactions of alkenes with lanthanide elements during the last fifty years. These reviews are particularly useful when one enters a new field of science, since they are normally extensive in their references to the original work. Thus, one can quickly and easily define the scope of the field, the primary researchers in the field, and the journals of particular interest for the field (i.e. are Tetrahedron and the Journal of the American Chemical Society the main journals of interest or are Biochemistry and Journal of Organic Chemistry the journals one should be reading in a new domain?)

Secondary References

Many secondary sources exist which compile the vast quantity of information contained in the primary literature. For example, Chemical Abstracts (the world's largest index according to Guiness) publishes a few words about every article in the literature from anywhere in the world which remotely pertains to chemistry. Furthermore, the Abstracts collection contains information on all patents published (foreign or otherwise).

Though Chemical Abstracts is extremely useful, its sheer bulk makes simple searches complicated affairs. Indeed, the best way to use Chemical Abstracts is through its automated computer search facility (which costs a lot of money, unfortunately). Thankfully, several sources exist for organic chemists which reduce the effort involved in simply obtaining a melting point or synthetic procedure.

Among these secondary sources one finds The Merck Index, CRC Handbook of Chemistry and Physics, CRC Handbook for Identification of Organic Compounds, many chemical company catalogs (notably the Aldrich catalog), and the Beilstein collection. Unfortunately, Beilstein was published entirely in German. There are, however, useful little dictionaries which can get you around that pitfall (assuming that you aren't already fluent).

Tertiary References

By tertiary references we are generally referring to textbooks, such as laboratory manuals. It is unlikely (or at least uncertain) that the authors went to the original (primary) literature before publishing the melting point of some material in their book. The melting point which they report is probably taken from one of the secondary sources listed above and, as such, is merely a step away from hearsay. By the time the book is published there have been numerous possibilities of a little mistake slipping in.

Internet Resources

Begin to explore the multitude of information which exists for chemists on the web. This resource is only in its infancy. In the future it will be even more important. If you run across a useful web page that you think others in the class would want to know about, email the professor. We might add it to the list below. Students who alert the professor to a relevant online journal will receive bonus credit which will increase the final laboratory grade in the course. In order to receive this credit the student must be the first to bring the source to the professor's attention. Further, the professor must agree that the online journal has significant organic chemical relevance to merit inclusion in this collection.

Note all links were active as of this writing (); however, links are often broken. If you discover a broken link below please email the professor with the full information of the address of the broken link.


Tutorial on Information Resources
Internet Chemist


General resources
Physical Science Information Gateway
Web-ster's Organic Chemistry - outstanding portal
NIST Scientific and Technical Databases
NIST Chemistry WebBook
American Chemical Society
ChemWeb.com (free registration required)
Chemical Abstracts Service


Patents
United States
England
Japan
Germany (in German)
France (in French)


Academic department pages
Colby College, Maine, great organic resources Imperial College, London, for example, Drugs
University of Liverpool, England, Links for Chemists
University of Canterbury, New Zealand, Chemistry Portal
Universität Potsdam, Germany, LinkCenter


Books, abstracts and journals
Organic Syntheses

List of online-only journals
Japan Science & Technology Information Aggregator
ScienceDirect
Beilstein Abstracts

European Polymer Federation
The Alchemist
New Scientist
Chemical Journal on Internet, China
Chemical & Pharmaceutical Bulliten
Chemistry Letters
Chem-Bio Informatics Journal
Journal of Chemical Software
Journal of Computer Aided Chemistry
Journal of the Chinese Chemical Society, 1997-2002
Journal of Organic Chemistry, Online Journal, ARKAT-USA
Acta Chimica Slovenica
The National Academy of Sciences of Belarus
South African Journal of Chemistry University Chemistry Education, England
International Electronic Conference on Synthetic Organic Chemistry
International Journal of Molecular Sciences
Molecules, Online Journal, Switzerland
Internet Journal of Chemistry, free abstracts only


Corporations
MDL (Autonom, Chime, ISIS/Draw, US
ChemExper, Belgium
Sigma-Aldrich Corp, US
Chemical Block, Russia


Special interest sites
UN Office for Drug Control and Crime Prevention, for example, Bulliten, 01/01/1958
H3+ Web Page, University of Chicago
Tutorials, Virginia Tech
The Assignment

This assignment presents a very real problem which the working organic chemist must face daily. Suppose you need to prepare a compound which has been made previously in your pursuit to create a new and beautiful organic molecule.

There are two approaches available: you can either try to figure out the preparation of this molecule yourself or you can go to the literature to learn of its preparation. Clearly, the latter approach seems less difficult, thus, off we go to the library.

To complete this assignment, you will do the following:

1. Obtain the melting point (or boiling point for a liquid) of your molecule by using any other secondary reference work.

2. Obtain the melting or boiling point of your unknown by using Chemical Abstracts to locate an article written in English, French, Spanish, German or any other language in which you are fluent.

3. Prepare a report with the following:

Optional. A level of distinction is obtained by submitting a xerox copy of the original article along with your answer and its reference. This will not be possible for some of the problems assigned without going off-campus. This is not required.
General Procedure for Locating Organic Preparations Using Chemical Abstracts

Example: To find information about the synthesis of 3-chloro-2-butanol, you might follow this pathway:

1. Determine the Molecular Formula (e.g. C4H9ClO)

2. Use the Formula Indices from Chemical Abstracts to determine the CA name

3. If only a few references are given in the Formula Index, look up the references directly in the abstracts.

4. If many references are given, look up the Chemical Abstracts name of the compound in the appropriate Subject Index. (e.g. 2-Butanol, 3-chloro)

5. The Subject Index will possibly have an additional subheading reading:

Preparation
Properties
6. Look these up! They have the information which you are seeking.

7. Hopefully, these reference articles are in English, French, Spanish, German or a language which you can read.

8. Hopefully, these articles are in a journal which Gordon receives.

9. If the above are true, look up the articles!

10. If not, HOPEFULLY the information which you need (e.g. melting point, boiling point) is found in the abstract itself.

Note:. All of the molecules given as assignments have been found in the Gordon College collection of Chemical Abstracts, referencing an article in English, French, Spanish, or German. If at first you find something that doesn't seem too helpful, keep looking. The information is in the "haystack" somewhere.