Tips on Searching the Scientific Literature for Benzophenone Project
CH 463/463H - 2003
Remember that you are looking for clues on the synthesis and characterization of your compound.
Sometime clues are found in unlikely places, such as in figures and tables in articles and may not be the
main emphasis of that publication, but these are like gold to you! One clue leads to another, and
eventually you find enough information that was published (and presumably reviewed by reputable
scientists!) to base the design of your synthesis on. Often it pays to follow up on secondary leads
through the reference list at the end of promising journal articles. Start by searching the secondary
references that lead you to the primary journal articles.
1. Locate the Chemical Abstracts Registry number for your compound (RN or CAS number.) This is a
unique identifier and is a very useful tag to search on. The RN/CAS's can be found in the Aldrich
Catalog/Handbook, most other vendor catalogs and on-line in the MSDS database. For example the
RN/CAS for unsubstituted benzophenone is: [119-61-9].
2. Locate some correct chemical names for your compound. For example, benzophenone is a parent
name and in IUPAC language it is the same as diphenyl methanone. For substituted benzophenones, 4-iodophenyl-4'-nitrophenyl methanone is the same as 4-iodo-4'-nitrobenzophenone. Symmetrically
substituted benzophenones are named as bis (phenyl) methanone, e.g., bis (4-iodophenyl) methanone is
the same as 4,4'-diiodobenzophenone.
3. Scifinder Scholar electronic search engine - 3 or 4 simultaneous copies for the entire campus - for on-line searching of Chemical Abstracts. Use it efficiently and then log off so the next person gets a chance. The SciFinder Scholar interface is installed on the computers in GBAD 311 and it is on the PC's that run Oasis at Valley Library (look under networked databases.) This is the electronic version of Chemical Abstracts. There are limitations depending on how you search and which database is searched (there are several such as Registry, CAReacts, etc.) Success also depends on the date the journal article was published. For example, it is better to look for the older abstracts (before ~1975) by searching the chemical name of your ketone as a RESEARCH TOPIC rather than searching the compound as a structure. Searching the structure should however lead to the RN if you can't find it somewhere else. If you get a lot of hits, refine your search by searching the first hit list with another TOPIC such as synthesis of, preparation of, spectroscopy of, etc., to narrow down the choices. Check the box next to the likely candidates and select the microscope icon to view the abstract. If a computer monitor icon shows up you can get an electronic copy of the article directly through ChemPort, ask for help if you need it.
4. Go to the Beilstein Centennial Index (paper), in basement of Valley Library. The Centennial Index covers all the paper Beilstein in one fell swoop! The references from the Centennial Index send you to the exact volume where you will find the abstract of the primary literature. You will need the formula for your compound listed out as: CnH2n-16O. Benzophenone itself is called monooxoverbindungen. (Yes you guessed it, these abstracts are in German! However, they are detailed and sometimes can give enough information so you can design your synthesis.) Most of the 463 compounds are in Band VII but not all (not if you have -OCH3.) The substituted derivatives directly follow the benzophenone parent entries.
5. Go to the paper Chemical Abstracts, basement floor of Valley (pre 1967) (post 1967 are on compact shelves). Look up either the chemical name, chemical formula or the RN (limited use to post 1957) in one of the cumulative indices - this sends you to the Chem Abstracts volume where you will find the abstract of the primary journal article which hopefully has something to do with your compound. (Don't get discouraged, there are often false trails. Keep on trying and check with your Instructors frequently!)
6. Check Oasis (Valley Library Catalog) and Orbis (collection of university libraries that we can get
articles from). This can be done remotely from
http://osulibrary.orst.edu/. You
may have to request interlibrary loan to get an article if Valley doens't have
it on the shelf.
7. Check your organic text book and other organic text books for Friedel -Crafts acylation reactions using aluminum chloride as the catalyst. Look at the references in the text book also.
8. If you can't find ANYTHING on your compound, try a similar one to see if more is published on it and adapt that procedure. For example, if you are assigned 4-chloro-4'-propylbenzophenone and can't find ANYTHING, try looking up a preparation for 4-chlorobenzophenone or 4-chloro-4'-methylbenzophenone or 4-methylbenzophenone and design your own synthesis (the Instructors are available to help.) You can also look at Method 2 in the lab manual and use this as a first guess.
Key words to watch for in your search:
Part A of Project - Synthesis and characterization
Keep eyes open for and note references for Part B of Project - Photophysics and Photochemistry: