the chemical information instructor
edited by ARLEEN SOMERVILLE Carlson Library
University 01 Rochester Rochester,NY 14627
Undergraduate Organic Chemistry Students Use Printed and Electronic Handbooks to Identify Unknowns Grace Baysinger Swain Chemistry and Chemical Engineering Library, Stanford University, Stanford, ~ ~ 9 4 3 0 5 ' During the fall quarter, approximately 400 students at Stanford University take Chemistry 1301132, a sophomore-level organic chemistry class. Students use library resources intensively in the Swain Chemistry and Chemical Engineering Library to help them identify unknown compounds they are working with in the laboratory. Chemistry majors (10-15% of the class) have eight unknowns and non-chemistry majors have four unknowns that they must identify Students also have to synthesize a derivative for each compound. Laboratory reports must include citations to confirm observations and a n IUPAC name as well a s synonyms for their compounds. Students use a variety of titles in the library to help them identify their compounds. Materials include core textbooks and a number of chemical handbooks. Spectral sets are offlimits, so students learn to use reference materials instead of flipping through spectral sets until they find a match. For the last two years, we experimented with teaching students how to use chemical handbooks in electronic format as well as some software products. Using online resources helps prepare students for the information age, eases crowding in the library by shortening the amount of time it takes students to find needed information, and reduces competition for access to multi-volume sets and subsequent damage from overuse to these sets. Here's a brief description of the program put in place to provide library support for Chemistry 1301132. Early in the quarter, 3 1 teaching assistants (Tks) receive a 1.5hour training session from the Swain Librarian on how to use printed Beilstein and how to search Beilstein Online and the Chapman Hall Chemical Database. A week later, students taking the course receive a 50-min lecture that includes both print and electronic resources. Handouts covering a bibliography of resources and "cheat sheets" to further acquaint students with resources also are distributed to the class. Students then complete a library exercise where they gain experience using reference materials to locate known compounds. To insure equitable access to electronic handbooks, we created a reservation system where students could sign up for two 40-min time slots per week. The Swain Library Materials Fund, a n Undergraduate Fund, and a Database Searching Fund were used to pay for electronic resources. TA's provide in-depth reference help in the library for 25 hours per week. The library staff provides reference help on-demand as needed. Because of the large number of students and intense use of the library, having TA's provide reference assistance is essential. During the first several weeks of the course, the learning curve is steep for students and labor-intensive for 'Ernail address: GraceBQLeland.Stanford.edu.
library staff and TA's. Fortunately, the amount of effort needed levels off as students learn different search strategies and become familiar with library resources. Printed Resources Though an increasing number of resources are becoming available in electronic formats, many sources still are available only a s printed works. Titles used include selected core textbooks, one-volume handbooks such a s the CRC Handbook of Chemistry and Physics and the Merck Index, and multi-volume sets such as Dictionary of Organw Compounds a n d Beilstein's Handbook of Organic Chemistry (see Appendix 1). The number of compounds covered and properties listed varies from handbook to handbook (see the table). Instead of consulting one or two reference books, students must do quick lookups in a number of sources to find the information they need. Strategies include using physical property indexes such a s melting point, boiling point, molecular formula, and molecular weight. Because spectral data, obtained during laboratory experiments, provides information on functional groups present in a n unknown, sources arranged by class of compound (e.g., CRC Handbook of %bles for Organic Compound Identification) are particularly useful. Beilstein i s used heavily because i t contains authoritative data and is the most comprehensive source of information on derivatives. The time it takes for students to locate their compound can vary considerably. For example, the number of compounds melting within a certain range may be quite large. Imprecise lab data may force students to search a broader range of values within a n index. Because only one index can be searched a t a time, lookup work can be tedious. Indexes that contain two pieces of information; e.g., a molecular formula index that includes the names of compounds (e.g., Dictionary of Organic Compounds), helps minimize the time spent following stray leads. Sources that display all data available in a matrix format also help students use time effectively and efficiently (e.g., The Aldrich Microfiche Library of Chemical Indices). After students identify their unknowns, they frequently search by the name of their parent compound to verify information they already have collected, to look for additional information, and to identify possible derivatives. Variations in nomenclature and permutations of names are a common problem in chemical name searches. Systematic searching by all possible permutations, consulting synonym indexes, and using molecular formula indexes are valuable methods to determine where a compound is located in other sources. Volume 72 Number 12 December 1995
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Factors to Consider Regarding Use of Electronics Resources in a Course Does it make sense pedagogically for students to use online sources for the course? What titles best meet the needs of the course? What funds are available and what options provide the mast effective and efficient use of resources? What types of hardware and soRware are needed to use electronic products and to view search results? .Haw manyhaw easy are the search interfaces students would need to learn? W h a t facilities work is needed to support the use of electronic resources? What staffing resources are required for training, consulting, and maintaining equipment? Because Chem 1301132 students use t h e Library intensively throughout t h e quarter, i t is a n ideal course to introduce online searching. Students primarily accessed two electronic chemical handbooks from Knight-Ridder (for-
merly calledDialog). Beilstein Online, the largest chemical handbook of organic compounds, may have up to 300 indexes for each compound i n its database of 6.5 million records. The Chapman Hall Chemical Database, which includes the Dictionary of Organic Compounds, h a s several dozen indexes for searching i t s database of more t h a n 175,000 compounds. Instead of looking through one index a t a time in printed handbooks, students can search several indexes simultaneouslv i n t h e online version. The electronic handbooks wereaccessed using Knight-Ridder's Online Classroom Instruction Promam for Chemistry. Through experience, we learned that students needed ahout a 40-min tim~!-slotto do their online searches. Etcn though most studcnts were fnrniliar with computers, many had a difficult time wrth the'mechanical" asprcts ofunline searching, such a s capturing and viewing search results. To keep printing costs down, we encouraged students to download search results and copy them to a floppy disk.
Reference Materials Summary Physical Location Reserve
Number Compounds >12.000
On Pentium Computer Reference
nla >65 million
300 000 &r On Pentium Computer Macs (Si.Cls & S . 5 million Centris') Macs (Si,Cls& >175,000 Centris')
lndex Table
>15,000
lndex Table
27,000
lndex Table & Reserves
8.150
lndex Table & Reserves lndex Table
>175,000
On Pentium Computer lndex Table
>175.000
lndex Table lndex Table
10,000
IBM 386
27,000
All lBMs
nla
,7300
9.000
Title
Information Provided
n.p. b.p. m.w. m.f. name strum n.w m.p. b.p. dens desc deriv sol. IR ity data Aldrich Microfiche Libran yes yes yes yes yes no yes yes yes yes no no no yes of Chemical Indices no no no no no yes no no no no nameno no no AUTON0M:IUPAC only Naming Package no no no yes yes no yes yes yes yes yes yes yes yln Beilstein Handbook of Organic Chemistry (printed version) Bellstem C~rrentFacls In yes yes yes yes yes yes yes yes yes yes yes yes yes yln Cnem~stryon CD-ROM yes yes yes yes yln no yes yes yes yes yes yes yes yln Beilstein Online via Knight-Ridder yes yes yes yes yes no yes yes yes yln yes yln yes no Chaoman and Hall chemical Datatbase via Knight-Ridder yes yes no yes yes no yes yes yes yesa brief no yes no CRC Handbook of Chemistry and Physics CRC Handbook of Data yes yes yes yes yes no yes yes yes yes yes no yes yln on Organic Compounds yes yes no no no no no yes yes yes no yes no no CRC Handbook of Tables forOrganic Compound Identification yes yes no no no no no yes yes no no yes no no Criddle - Spectral & Chemical Characterization of Organic Compounds Dictionary of Organic no no no yes yes no {es yes yes yln yes yln yes no Compounds; Main Set and Supplements Dictionary of Organic yes yes yes yes yes yes {es yes yes yln yes yln yes no Compounds; CD-ROM Lange's Handbook of no no no yes yes no /es yes yes yes no no yes no Chemistry no no no yes yes no /es yes yes yes yes yln yes no Merck lndex no no yes no no no /es no no no no no no no yes yes yes yes yes no /es yes yes yes yes Properties of Organic Compounds on CD-ROM no no no no no yes no no no no no SANDRA:Structure & Reference Analyzer for Beilstein
'Specific gravity given
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Journal of Chemical Education
BeilRef. no no yes yes yes no yes yes no no
no no yes no no
no yes yln yes no
no
no yes
Used disks were reformatted and piven to students if thev didn't have a floppy disk. ~ u r i &peak periods, seven workstations were booked during all hours the library was open. Last year, students logged 1,000 connect houri and displayed more than 177,000 records. I n October 1994, alone, students logged 615 connect hours. Here i s a typical sample search students might do in Beilstein Online to find compounds that have a melting point from 145 to 155 degrees Celsius and that contain the elements carbon, hydrogen, and nitrogen. From spectral data i n the lab, the students might also know that they have from 1to 3 nitrogens. S MP=145.00:155.99 and ME=CHN and EC=N0001:N0003 where MP is melting point, ME is molecular elements, and EC is element count. It is interesting to note that prior to using online files, students would consider themselves "done" when thev found data i n a printed reference handbook that match& what thev had observed in the lab. However. because electronic handbooks usually contain both the'data on compounds a s well a s the journal citations where the data came from, many students now go on to look up the citations for more details. Students also used several CD-ROM's and software packages in the course that were loaded on two additional workstations. CD-ROM's used include CRC's Properties of Organic Compounds, the Dictionary of Organic Compounds on CD-ROM, and Beilstein Current Facts. While students found navigation a hit tricky, they liked being ahle to search physical properties and substructures a s small a s a functional group in the Dictionary of Organic Compounds on CD-ROM. Software programs used were SANDRA, where a user draws a chemical structure to find out where a c o m ~ o u n dwould be located in ~ r i n t e dBeilstein (because thLprinted version i s organizeti by chemical structure), and AUTONOM, a program that provides a n IUPAC name for a chemical structure. While the electronic resources listed above had to be used i n Swain, Residential Computing a t Stanford helped the Library make Introduction to Spectroscopy, a HyperCard tutorial program, available over the campus network. Access was managed using Software Librarian, a Macintosh software management program that was developed by Residential Computing. Software Librarian is available for use by other institutions (see Notes section a t end of article). Hardware and Software
Chem 1301132 students used seven Macintosh computers for searching Knight-Ridder files and two IBM computers for searching CD-ROM's and software. An additional Macintosh used to support reference work also was available for students to useL* one of the seven Macs had a hardware failure. TA's and the librarian also used the reference Mac workstation t o consult with s t u d e n t s on searches. All workstations are connected to our campus network and to the Internet. The two IBM's have dedicated laser printers and the eight Macs have shared access to three laser printers. Software programs used for searching the Knight-Ridder files included: MacSamson, a telecommunications software package developed at Stanford, far accessingfiles through the Internet and for downloading search results, Microsofi Word, a word processing program, to viewlprint search results;
Fetch, a file transfer program, to move files electronically from a workstation at Swain to another server on campus; and a folder.
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At Ease enabled us to restrict access to the "KniehGRid~ der Folder" to members of the class even though the workstations are located in public areas. To facilitate logon, a MacSamson script was created. By double-clicking on the Knight-Ridder script icon, students were automatically logged into the Knight-Ridder system without seeing the Knight-Ridder account number and password. Budget Knowing what type of passwords and how many to acquire was an important question. To help users, KnightRidder offers several types of accounts for Classroom Instruction Program users. These accounts are "pay as you go" a t a rate of $15lconnect hour or "fixed price" of $1,500 per password per year. Because of the large class size, we decided to acquire fixed price passwords rather than risk running out of funds mid-way through the course if use was higher than expected. In 1993, we acquired five fixed price passwords for students to use and five $100 disposable passwords for training and consultation work. Students had one 25-min search appointment per week. Because 25 minutes was not enough time for students to finish their searches, in 1994 we acquired eight fixed price passwords and allowed students two 40-min appointments per week. We found t h a t for intensive use, having one password per 50 students is adequate. The decision to buy fixed price passwords was a good one. While $8,000 was spent to pay for fixed-price passwords i n 1993, the same amount of searching would have cost $16,000 if paid by the connect hour. A word of caution, Knight-Ridder monitors use of its Classroom Instruction Program accounts carefully hy examining the equivalent commercial dollars spent by CIP users and will turn off a n account if they deem use to be excessive. Even though their CIP program is the most generous one among the online vendors, we had our accounts shut off once because the commercial rates for using Beilstein Online a n d CHCD a r e high and the number of students ~ a r t i c i ~ a t i ui ne the Droeram was u large. Fortunately, prbmpt ebmmlnication with KnightRidder to review our roer ram ma tic efforts and trainine plan enabled u s to continue our search program even though we were a t the upper threshold of their limits for CIP use.
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A
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What's Next The Chem 1301132 students strongly endorse continued use of electronic resources (see A ~ ~ e n d2). i xFuture directions for library support of this cia'ss include:
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installing an Internet connection in the classroom in order to do demonstration searches during the library lecture; making handouts for the course available on the campus network; establishing a computer classroom/ laboratory at the Swain Library for instruction in computerized resources; continuing to provide access to electronic handbooks; and if possible, making electronic handbooks available via the campus network.
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Appendix 1. Class Bibliography A. General Texts
Cheronis, N. D.; Entrikin, J. D.; Hodnett, E. M. Semimicm Qualitative Organic Analysis: The Systematic Identification of Organic Compounds, 3rd ed.; R. E. Krieger: Malabar, FL, 1983: pp 1060. Volume 72 Number 12 December 1995
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Criddle, W. J.; Ellis, G. P. Spectral and Chemical Characterization of Organic Compounds: A Laboratory Handbook, 3rd ed.; Wiley: New York, ~ 1 9 9 % pp 119. Memory, 3. D.; Wilson, N. K. NMR of Aromatic Compounds. W h y : New York, c1982; p 252. Pasto, D. J.; Johnson, C. R. Organic Structure Determinution. Prentice-Hall: Englewoad Cliffs, NJ, 1969: pp 513. Pavia, D. L.; Lampman, G. M.; Kriz, Jr., G. S. Introduction to Spectroscopy:A Guide for Students of Organic Chemistry. W. B. Saunders: Philadelphia, 1979; pp 367. Shriner, R. L., et al. The Systematic Idzntification of Organic Compounds: A Laboratory Manual, 6th ed.; Wiley: New Yark; c1980: pp 604. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed; Wiley: New York, 1991; pp 419. Streitwieser, Jr., A,; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed: Macmillan: New York, 1992.; 1v. (various pagings). Vogel, A. I.; rev. by Furniss, B. S. et al. Vogel's lbxtbook ofPraetical Chemistry. Including Qualitative Organic Analysis, 5th ed.; Wiley: New Yark, 1989; pp 1514.
6. Printed Reference Resources The Aldrich Microfiche Libmry of Chemical Indices [microform]-Ndrich Chemical: Milwaukee, WI, 1990: 26 microfiche. Beilstein Handbook of Organic Chemistry. Compiled by the Beilstein-Institut fur Literatur der Organischen Chemie; Springer-Verlag: Berlin; 1779-1979. CRC Handbook of Chemistry and Physics, CRC Press: Cleveland, OH. CRC Handbook of Tables for Organic Compound Identification: Compiled by Rappoport, Zvi; 3rd ed; CRC Press: Cleveland, OH, 1967; p 563. Dictionary of Organic Compounds, 5th ed. Chapman and Hall: New York; 1982; 7 v. and supplements. Dean, J. A.Lange$ Handbook of Chemistry, 14th ed; McGrawHill: New Yark; cl992; 1v. (various pagings). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. Budavari, S., Ed.; 11th ed., centennial ed; Merck: Rahway, NJ, 1989; 1v. (various pagings). Table of molecular weights : a companion volume to The Merck Index, 9th ed. Martha Windholz e t al., Eds. 1st. ed.; Merck: Rahway, NJ, 1978; pp 257.
C. Electronic Reference Resources AUTONOM: PC Software for Systematic Names in Organic Chemistry:PC-Version 1.1.; Beilstein Information Systems: Frankfurt am Main. Germanv. .. c1994. Beilstein Online [Computer File]. Accessed file for this class via Knight-Ridder's Chemistry Classroom Instruction Program. Beilstein Current Facts in Chemistry(CD-ROMI;Beilstein Institute: Frankfurt am Main, Germany; 199011991CHCD Dictionary of Organic Compounds [CD-ROM]: Chapman & Hall: London. 1993. Chapman Hall Chemicalatabase, [Computer File]. Accessed file for this class via KnightrRidder's Chemistry Classroom Instruction Program. Prooerties ~,~~ o f Organic Comoounds ICD-ROM1: Version 4.0. CHC I& Gcil R ~ I ~ F cL1995 , SAN1)IU 1Snftwarel; PC-Version I 0; B r ~ l s t e ~Inrtltute: n Frnnkfurt am Man. Germanv, 1989 ~
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Appendix 2. Results of Student Survey Surveys were distributed to students n e a r t h e end of t h e Fnll Quarter 1994 to eet their ftvtdhack on their use of t h e ~ n i & ~ i d d e r f i l e s , k h a t difficulties t h e y encountered, a n d w h e t h e r thev found access t o electronic chemical handbooks useful"to them in their coursework. Tweutyseven nercent of the students (110 students) responded t o the survey. Below is a summary of their comments.
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Journal
of Chemical Education
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Did you search the databases available via Knight-Ridder? 95% Yes 5% No Which databases did you search? 75% Both Beilstein Online and Chapman Hall Chemical Database 19% Only Chapman Hall Chemical Database 3% Onlv Beilstein Online 1% No ;esponse .What types of search techniques did you use searching? (check all that apply) 88% Boolean Logic 27% Proximity Operators (closeness of terms to one another) 19% Expanding Indexes 11% Truncation 4% No response What types of searches did you perform? (checkall that apply) 97% Melting PointiBoiling Point 92% Molecular Weight 91% Molecular Element 69% Element Count 57% Chemical Name 52% Molecular Formula 7% Refractive Index 5% CAS Registry Number 3% Name Fragments 2% Chemical Class Name 1% Relative Density 1% Beilstein Registry Number 4% No response Haw did you capture your searchresults? (check all that apply) 48% Wrote data down by hand 45% Saved search on hard disk and cooied to floonv disk 37% Printed screens as needed 32% Saved search on hard disk and printed out on paper 5% Did not capture search results 3% Saved search on hard disk and FTPed search results to another computer 5% No resoonse
.."
6% No respanse H o w easy was it to use the Chapman Hall Chemical Database? 56% Easy 29% Moderately difficult 4% Difficult 3% Didn't use it 8% No response How easy was it to use Beilstein Online? 55% Easy 31% Moderately difficult 5% Difficult 2% Didn't use it 8% No response How easy was it to capture search results? 66% Easy 23% Moderately difficult 7% Diff~cult 4% Didn't do it 6% No response On the average, how much did you use Knight-Ridder files during the course? 2% Couple of times a day 1% Once a day 16% Couple of times a week 33% Once a week 28% Couple of times a month 8% Once a month 3% Two times 2% One time 6% No response Regardless of application, how familiar are you with using computers? 23% Very familiar
40%Familiar 23%Somewhat familiar 8% Not very familiar 0%Unfamiliar 6%No response Did you find using Knight-Ridder's computerized datahases helpful in your lihraw work? 26% Very useful 28% Useful 32%Sometimes useful 8%Not useful 6%No response Would you recommend that computerized database searching be used in the course next year?
.
80%Yes 6%No 7% Don't know 7% No response
Notes Ron C. Cooke prepared an excellent manual to search KnightRidder chemistry files. This manual is called Onliw Searching Clrrriculurn for Chemistry. I t is accessible via anonymous ftp at oavax.csuchico.edu pub:chemistry.dir. Software Librarian: for more information go to this WWW address: http:llrescomp.stanford.eddsoftlib.html or send an email message tc
[email protected].
Volume 72
Number 12 December 1995
1111
