The program is written in Applesoft Basic language. I t is very easy t o make any changes in these programs in order to work with other interface systems. A free copy of Microcomputer Interfacing Programs may be obtained by writing t o the author. These programs and three sample experiments, ones used to obtain the data presented here, are also available on disk for $12 (including manual).
Searching the Chemical Literature: An Individualized Librarv Exercise using a SERAPHIM
Give at least three names for your compound (i.e., generic, brand name, IUPAC, ete.), and cite the sources for your information, Give a complete citation for at least one paper on the synthesis of this compound, and attach a photocopy of the CA abstract to your pet a copy paper? report. Where and how could .you . ~.of the . Give a complete citation for a paper about the pharmacological activity of this eompound. Where could you get a copy? Attach a copv .. of the ahstract to your rewrt. Using the Science Citation Index (SCI) find out how many times the pharmacology article was cited in 1964. Give a full citation for at least one pamr that cites the phmacolow -.article, and attach a photowpioithe SCZ page to ;our report. (For extracredit, obtain copies of both your cited papers and write a 1-page summary of their contents. Attach the original papers to your report also.)
After a brief library orientation, the students were allowed eight weeks t o complete the report, including time necessary for interlibrary loans t o be processed. University of Wisconsin-Parkside The amount of library time actually spent on a typical 3Kenosha, WI 53141 page report ranged from about 5 h to more than 50 h; the Organic chemistry students are often introduced to the averaee time was between 10 and 15 h. About half the stuchemical literature through exercises in their laboratory dengworked on the extra credit assignment. The students manuals; these exercises generally consist of a series of unreenjoyed working with the program and worked hard a t getlated questions that briefly expose the students to a large ting a compound with "good" activity, then expended serinumber of chemistw sources. However, these exercises do ous effort working on a good report. They were especially not really resemble a t r u e literature seareh, and the students attracted hy the iaea of &signing their own molecule. tend to share data, minimizing their actual exposure to the In the initial run of this exercise the Design-A-Drug proliterature. Later courses that require detailed literature gram generated a numher of compounds with no literature searches also need t o review the basics. references, yet high reported hiological activity. The probSeveral criteria can be established for a better introduclem was traced 6 the manner in which the promam calcutory exercise. I t should provide each student with a series of lates activity: it is a weighted calculation based on substituauestions about a uniaue com~ound.so that students need ent position and structure but is not directly related to tb use the literature i n a manner moie consistent with typireported activity. Modifications to the program were made cal research ~roblems.Such individual, but related.. assignthat minimized this problem; we were also able to speed ments would avert the pooling of specific information to student use of the program with code changes tbat facilitatsolve auestions but would allow the students to help each ed data retention between trials and eliminated timed waits. other &th general research techniques if necessary and a t A few other problems appeared as well. In their eagerness the same time would give the students a sense of having a to get a "good" compound, students often duplicated each coherent, realistic prol&m tosolve for themselves. However, other's results; instructor review of the compounds chosen the problems assigned should not be toodifficult since these minimized this. Students also sometimes wanted to count students are just beeinnine their serious study of chemistry for extra credit articles in foreien lan~uapestbat they could -.~~-~~~~ of the and have not previously been exposed to the chemical literanot read, but the student summat$ ( n i t a ture a t all. Enelish abstract) was reauired for any extra credit. This paper reports an individualized literature exercise Evaluation of'the student work was based on complete that fulfills these criteria and has been used successfullv for and reasonable answers to the questions, judged with referseveral classes of organic chemistry laboratory student;. ence t o the photocopied materials included. Summaries for Molecules for each report were generated by the students extra credit could usually be evaluated in comparison with themselves, using the SERAPHIM program i ) e s i g n - a - ~ r u ~ the abstract of the pape; in question and were counted less (SERAPHIM Disk IR 701). 1)esign-a-Drug investigates the heavilv if they merely copied an abstract or other sections of pharmacological activity of a number of tricyclic aniidepresa pap& writing stile, grammar, spelling, and effort were sants by allowing the operator to build u p a specific molecule also given some weight. The exercise has been found narticularlv suitable for an on a tricyclic base; variations in substituents can be made a t ---. ----five different positions, and for each specific molecule made organic chemistry course since i t relates t o organic synthesis the Dromam returns a calculated bioloeical activitv. Thus of comoounds relevant t o the "real world" and allows the the operator can examine a large number of molecules for student t o relate biological activity t o molecular structure. activity and build up a body of information from which Copies of the program can be obtained from the author, structure-activity relationships can be determined. For this along with a more detailed discussion and a list of successful librarv exercise. each student was reauired to use the proreferences. g r a m t o design' a molecule for investigation that had an activity of a t least 75 on the promam's rating scale of 1-100. This activity waschosen in oidei to minimize false starts for the students; the hope was that any compound with activity Huckel Molecular Orbitals that great would b e a well-known, easily found compound John J. Farrell and Harry H. Haddon with commercial application and many references. Franklin and Marshall College The students were asked to answer nine questions about Lancaster, PA 17604 their compounds: G. Lynn Carlson and Erlk Womeldorl
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What is the structure of your pharmacologically active compound? What type of biological activity does it have? What is the correct numbering system for the ring system in your compound? What is the CA registry number far this eompound?
Program Huckel Molecular Orbitals (Version 2.3) calculates energy eigenvalues, eigenvectors, pi-electron charge densities, and pi-electron bond orders for conjugated and aromatic molecules using the assumptions of simple Huckel molecular orbital (HMO) theory. Each of these parameters Volume 66
Number 10 October 1989
839
