An Integrated Chemical Information Program - ACS Publications

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Chemical Information Instructor

Andrea Twiss-Brooks John Crerar Library University of Chicago Chicago, IL 60637

An Integrated Chemical Information Instruction Program Arleen N. Somerville† and Susan K. Cardinal* Carlson Library, Department of Chemistry, University of Rochester, Rochester, NY 14627; *[email protected]

Chemical educators have long recognized the importance of teaching their students how to locate and use chemical information (1). Many articles have been written about standalone courses and about efforts that focus on teaching specific topics within a course or two (2). At the University of Rochester, however, chemical information instruction is integrated into courses throughout the undergraduate and graduate curriculum in a sequential manner. Students utilize their information-seeking skills in completing course work and then this information serves as the base on which to continuously build new skills. This article describes the program as implemented over the past four years, notes how the faculty and librarian work together in conjunction with student input, and depicts how the instruction contributes to the educational value of the courses. The University of Rochester is a small, private research university with innovative programs for undergraduates and strong graduate programs. The chemistry undergraduate program offers the flexibility of moving between the B.A. and B.S. programs. In addition to the B.A. requirements of general chemistry, organic chemistry, inorganic chemistry, and physical chemistry, B.S. students take chemical instrumentation, molecular spectroscopy, and advanced laboratory techniques courses, as well as eight credits of senior research. Two courses must be taken as upper-level writing courses. Most students begin work in research labs before their senior year. They also have a chance to participate as leaders of general and organic chemistry workshops, peer-led groups that meet to analyze chemistry problems and reason out solutions (3). The need to ensure that students develop informationsearching skills was recognized by the chemistry department and the library in the mid-1970s and was accelerated in 1979 with receipt of a National Science Foundation grant to develop an “integrated chemical information curriculum” (4). Since 1979 the program has changed with the curriculum, with evolving information resources, and with input from students and faculty. Throughout these years, the program has matured and contributed to the educational value of the students’ experiences, so that the chairman regularly comments that the “chemical information program is an integral part of a University of Rochester chemistry degree”. The program is successful in meeting the chemical information needs of our chemistry department. We attribute this success to a number of factors: 1. Chemistry faculty and chemistry librarians collaborate closely and communicate effectively with each other. †

Arlene N. Somerville ([email protected]) was the Chemistry Librarian, Carlson Library 1968–2000 and Susan K. Cardinal is the Chemistry Librarian, Carlson Library from 2000 to date.

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2. Chemical information instruction is connected to specific course assignments. 3. The instruction is sequential—that is, each semester is based on information skills used in previous courses. 4. The instruction is as interactive as possible—that is, it involves hands-on and small group discussions when possible. This technique is especially popular with students. 5. Because information instruction is an accepted and integral part of department’s program, new faculty willingly include information segments in their courses. As faculty change courses taught, they continue the information components from the previous instructor. 6. New resources and new computerized formats are incorporated on a continuous basis. 7. The librarian actively supports the chemistry department’s orientation, education, and research programs by providing customized, knowledgeable, and need-based instruction.

Two elements of the program’s success warrant additional description. Firstly, faculty–librarian collaboration underpins the whole endeavor. Ongoing discussion occurs among the librarian and faculty who teach courses that require use of information resources, so that the librarian thoroughly understands the educational and scientific intent of the assignments and can update sources and research techniques to meet changes in course content. This enables the librarian to teach using relevant examples, thereby addressing specific student needs in the context of course assignments. Attending the class when the assignment is discussed aids this understanding. The relatively small classes and location of the library in a building connected to the chemistry department support these efforts. The faculty–librarian discussions work best for a librarian with a background in science, preferably a chemistry degree, and a thorough knowledge of both the chemistry curricula and chemistry resources. A new librarian can improve chemistry knowledge, understanding of course content and curricula, faculty teaching techniques, and preferred information resources by sitting in on courses and diligently networking with chemistry faculty. Occasionally even the most conscientious faculty overlook the library instruction or question the need to include an information component in a crowded course schedule, so the librarian needs to be proactive. The value of the information segments can be justified by discussing how they support the educational objectives of the professor and describing the positive comments of students in previous classes or questions that have recently been asked at the reference desk. Also,

Journal of Chemical Education • Vol. 80 No. 5 May 2003 • JChemEd.chem.wisc.edu

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successful discussions with faculty may include joint review of a draft version of proposed content of the information segment (what resources will be covered and how) and negotiation of time and place. Flexibility by the librarian will open various scheduling possibilities, such as meeting with the full class in a laboratory lecture class or in small groups during a lab. Sometimes classes and laboratory sections, small group appointments, and special workshops (e.g., new features of SciFinder Scholar or CrossFire) might meet in the evenings. While some of these options require that the librarian work outside of a 9–5 schedule, it achieves the desired integration objective and a continuation of the program with changing curricula and resources. Additionally, effective librarian support of faculty research demonstrates how the librarian’s efforts aid them and their research group. Then the faculty may be more receptive to having the librarian work with their students as part of their courses. Secondly, the meaningful connection between chemical information, instruction, and students’ coursework promotes successful incorporation. Faculty regularly report that students tell them the information instruction was useful, and they see that students’ work reflects understanding of information resources and searching techniques. Students find the instruction relevant because it enables them to be more successful in their courses. Students’ comments on surveys provide information about what specifically helped them (“I learned how to use the online resources and how to look up spectra. This will be very helpful.”), what additional information they would like to know (e.g., more details of searching CrossFire), and what was less useful or not clear. Lastly, exploiting the resources and ubiquity of the World Wide Web means more materials are more easily available to students. Handouts are now being converted to the Chemistry Resources Web with links from course Web pages. (To find the current Web pages, go to http://www.lib.rochester.edu [accessed Jan 2003]. Look for link that says “Course resources/ reserves” and find pages for the chemistry department.) Overview of Information-Searching Instruction The sequential integration of student course needs and information skills and knowledge into the chemistry curriculum is highlighted in Table 1. The remainder of the article describes how the instruction is developed, implemented, and related to course assignments. In addition to working with specific courses, the librarian schedules sessions for graduate students and postdoctoral fellows tailored to the specific needs of their research groups and refresher or update sessions for Beilstein’s CrossFire, SciFinder Scholar, and Science Citation Index, which are open to all undergraduate and graduate students, postdoctoral fellows, faculty, and research staff from all areas of the University, including the Medical Center.

First Semester General Chemistry Courses: 400 Students, Non-majors; 250 Students, Majors The chemistry librarian and other library staff attend the lecture classes when students are first assigned reserve-reading requiring use of the library resources. In ten minutes, the class meets the chemistry librarian and the circulation and reserve desk staff and learns about electronic reserves and the

existence of the science library and its facilities (location on campus, location of circulation and reference desks, various study options, and computer locations.) A PowerPoint tour is also made available, complete with staff photos, on the Web page of the course. This introduction breaks down barriers and encourages students to interact with library staff when questions arise. A recent assignment in the majors course required that the students seek information on such energyrelated topics as global carbon dioxide emissions and total energy consumption by G7 (Group of Seven) countries. This required Web use, so the librarian came to the class to provide a brief review of criteria for evaluating Web sites and provided examples of good and bad sites.

Organic Chemistry Laboratory: 250 Students, Non-majors Fall The chemistry librarian meets with the laboratory lecture class twice: first in October to introduce them to major sources of physical properties, such as melting points so they can differentiate isomers, and again in November for spectra sources when they have unknowns to identify. For physical properties, students learn the basics of using the CRC Handbook of Chemistry and Physics (5), Dictionary of Organic Compounds (6), Merck Index (7), Lange’s Handbook of Chemistry (8), Aldrich Catalog of Fine Chemicals (9), and several Webonly sources, including ChemFinder (10) and an Organic Compounds Database (11). A typical compound, such as 4methylbenzoic acid, is used to demonstrate the effective use of these sources and an efficient order in which to use these sources based on information needed and that provided by the various sources. A step-by-step search strategy is described. Students are provided a guide (now on the Web), developed jointly by the faculty and librarian, that specifies steps to follow to identify a compound from the spectrum and for locating a spectrum of a known compound. This guide is augmented by additional tips for analysis and print and Web resources. Use of these guides is demonstrated by following a typical substance through the process that the students would use. The group is large, but students take advantage of opportunities to make appointments with the chemistry librarian, who also is available for consultation with students as they work in the library. Spring To prepare students for a specific laboratory experiment, the nitration of naphthalene (during which students need to identify which isomer they have by comparing experimental data with published property values), the librarian reviews use the Dictionary of Organic Compounds (6) and alerts students to features not used in the previous semester, such as references to journal literature and properties of derivatives. A review of how to find journal articles in the library or on the Web is provided (so students can easily find journal issues). Again, a typical compound, such as nitrobenzoic acid with its various isomers, is used in the class lecture. Students who did not take either of the organic chemistry courses offered in the fall semester are encouraged to contact the librarian for an overview of information covered previously. In April, in preparation for students identifying unknowns that involve derivatives, new sources are introduced,

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Table 1. Introduction of Information-Seeking Skills into the Chemistry Curriculum Skill and Knowledge

Class(es)

Introduction to librar y and staff Library description and layout

1st semester general chemistry courses

Circulation and reserve library staff


Chemistry librarian availability; contact information


Electronic reserves


Evaluating Web resources

1st semester general chemistry, workshop leaders

Basic property sources Physical property resources

Organic chemistry labs

Spectroscopy resources; identification procedures


Advanced property resources, including derivatives


Key reference sources for inorganic chemistry

Inorganic chemistry courses

Original literature Introduction to Beilstein’s CrossFire


Introduction to SciFinder Scholar


Locating print and electronic journal articles

Organic chemistry labs; workshop leaders; advanced lab

Chemical education resources

Workshop leaders

Writing resources for chemistry

Workshop leaders, organic chemistry labs, advanced lab, inorganic chemistry, bioorganic reactions, advanced organic reactions

Introduction to Science Citation Index

Advanced lab

Journal article components; review articles

Advanced lab, advanced inorganic, bioorganic reactions

Introduction to Medline

Bioorganic reactions

Research projects Techniques for self-education

Advanced lab

Designing experiments

Advanced inorganic; bioorganic reactions, advanced organic reactions

Advanced reference sources for synthesis

Advanced organic reactions

such as CRC Handbook of Tables for Organic Compound Identification (12), Melting Point Tables of Organic Compounds (13), and several textbooks, such as Systematic Identification of Organic Compounds (14), and Experiments and Techniques in Organic Chemistry (15). A guide, jointly developed by the faculty and the chemistry librarian, provides direction for using the most important functional group of the derivative to determine melting or boiling point, using that information to identify possible unknown candidates, and taking into account spectra and various other properties to arrive at the correct identity. Again, the librarian is available for appointments and for consultation while working in the library. Because this experiment requires a good deal of information work, a guide for reference desk staff has been developed to aid their interactions with students when the chemistry librarian is unavailable. Information for derivative determination is also available on the Chemistry Resources Web.

Organic Chemistry Course: 60 Students, Majors Fall In October the librarian introduces students to sources for physical properties and spectra. The librarian meets in

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the library with groups of twenty students during their lab sessions. After a very brief review of the sources, the students are divided into groups of 4–5 and asked to spend approximately fifteen minutes becoming familiar with two sources, different for each group. For example, one group would review Aldrich Catalog of Fine Chemicals (9) and CRC Handbook of Chemistry and Physics (5). Each group uses the same substance (one similar to that used in the experiment) to examine the sources for such questions as: what information can be found, how is the information organized, and what would you do if the substance name was not found in the main alphabet index. The questions for Web sites, such as ChemFinder (10), vary. The librarian moves from group to group to be sure students do not get bogged down and to offer tips. Then, a student from each group reports to the entire group. Students take this reporting responsibility seriously, because they have been alerted that they are responsible for helping their colleagues learn what they need to know for the course. Students welcome the opportunity to learn by self-discovery. During the reporting period, the librarian adds essential information if it was omitted, or summarizes, if appropriate.



Spring In January an experiment about bromination of alkenes offers an opportunity to demonstrate how to use the Dictionary of Organic Compounds (DOC; ref 6) for additional information, such as original literature, and finding spectra, as well as introduction to Beilstein’s Crossfire (16). Of the several possible products of the reaction, one is found readily in DOC, a second is found via a journal reference from DOC, and the third requires use of CrossFire. Again, students come to the library in small groups from lab sessions. This time each group must locate a relevant journal article in the library and bring it to the librarian or locate it electronically. This requires following the procedure for locating journal issues, thus immediately putting instructions into practice. A general overview of CrossFire is given to all students and then they have time to practice during their small group time in the library, during specific consultation times, or as needed. The lab experiment requires using CrossFire to identify physical properties, identify products from their melting points, or draw a structure. In February, the librarian provides an overview of SciFinder Scholar (17) that highlights features students need to complete their experiments on the reduction of camphor with various reagents under different conditions. The librarian schedules times when lab teams could come in to use SciFinder Scholar, or they can come in for instruction as needed. The specific overviews of CrossFire and SciFinder Scholar are changed almost annually after discussions between the librarian and professor and as the course changes. Basic information about CrossFire and SciFinder Scholar are available on the library’s Chemistry Resources Web page.

Chemistry Workshop Leaders: 50 Students Students who lead the general and organic chemistry workshops take a course designed to provide them with group facilitation skills and additional chemistry knowledge to help their workshop group of 6–8 students work through assigned problems (3). As part of this course, the students write a paper about an aspect of teaching chemistry or a related subject of their interest. Students’ topics range widely and require use of resources from education, sociology, clinical and social psychology, cognition, and a wide range within science and engineering, in addition to chemistry. The chemistry and education librarians meet with the class to introduce them to a core group of these resources. Because of the large class size and the diverse topics, students are encouraged to make appointments with the chemistry or education librarian for personal guidance. Advanced Laboratory Techniques: 30 Junior Chemistry Students Students write up their laboratory reports as if they were submitting an article to the Journal of the American Chemical Society, which gives them knowledge of the contents of a research article and injects a real-life sense to their experiments. The first two experiments involve asymmetric epoxidation using a manganese catalyst and anionic polymerization of methyl methacrylate. In addition to the usual experimental details, students consider a set of additional questions that

extend the topic, such as the reasons for conducting an experiment at a specific temperature or why control of tacticity is important, for which students must use the primary literature. A guide, developed by the chemistry librarian in consultation with the faculty, lists resources for preparing papers (e.g., ACS Style Guide; ref 18), resources important for use with all experiments in the course (e.g., SciFinder Scholar, Beilstein’s CrossFire, and Science Citation Index; ref 19), and resources unique to the epoxidation and polymerization experiments (e.g., Comprehensive Polymer Science; ref 20). Students learn to use the print resources by working in small groups in the library, with reports from each small group to the entire class. Group questions include a discussion of how each resource helps answer questions for the experiments. This is followed by a class review of SciFinder Scholar (17) and Science Citation Index (19) to focus on special ways of searching effectively for information needed in this class, such as using other catalysts to achieve asymmetric epoxidation. Using lab questions from the class with the entire group working through the search makes the experience relevant and engrossing for the students. Using all of these resources provides information that enables students to write the paper’s introduction, results, and especially, discussion sections.

Advanced Inorganic Chemistry The students (junior, senior, and graduate students) are required to write a research proposal based on an original research idea. After the students are introduced to the assignment, the chemistry librarian spends the next class period preparing them to do the work that will help them identify potential topics, acquire the background information, and formulate ideas for the research design and methods. Discussions between the professor and librarian help make the presentation directly relevant and identify topics that can be used in the presentation. A typical sample topic has included, for example, charge transfer in cytochrome C. A list of resources (selected journals in inorganic and organometallic chemistry, selected annual review book sets, inorganic and organometallic chemistry compendia, encyclopedias, and data bases) is provided. More importantly, the librarian, in consultation with the professor, prepares a handout on tips for searching the literature when preparing proposals. In addition to providing general techniques for formulating a research topic and conducting searches, this targeted guide helps students determine whether the topic is original, locate articles to describe the background and significance, and develop the research design and methods segment of their proposal. The process of identifying a potential topic provides an opportunity for students to scan review articles that can be found by searching SciFinder Scholar or by scanning tables-of-contents of review journals and annual publications. They also learn about the importance of reading the introduction and especially the conclusion, which often note future work that requires more research, as well as following-up references from experimental sections of relevant articles. In this way students learn about the different parts of review and research articles. Finding relevant articles to use as models for research design and methods gives students another opportunity to use SciFinder Scholar.


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Bioorganic Reactions: Upperclass Undergraduate and Graduate Biology and Chemistry Students Students are required to prepare a research proposal for this course. As in the advanced inorganic chemistry course, students learn to find review articles, identify new research topics, and plan experimental details. Resources and tips for searching are distributed. Resources, such as dictionaries, SciFinder Scholar, Medline (21), and the World Wide Web are reviewed in class using vancomycin resistance as the sample topic. Students learn how to access electronic journals and learn to move between abstract journals and electronic journal articles. Because of the varying information-seeking backgrounds of the students (both biology and chemistry majors) and the need to cover the searching techniques in a class of about fifty, students have a chance to sign up for small-group sessions scheduled by the librarian. Advanced Organic Reactions: Upperclass Undergraduate and Graduate Chemistry Students In this course students are asked to design a synthetic route to any given organic molecule. The instructor emphasizes development of students’ ability to use primary literature as a source of practical knowledge. Early in the semester, students first work in small groups in the library to review several major reference sources, such as Organic Reactions (22), Comprehensive Organic Transformations (23), and Encyclopedia of Reagents for Organic Synthesis (24), and then the librarian provides a review of Beilstein’s CrossFire (16) and SciFinder Scholar (17). This review of electronic resources is an interactive group session that focuses on finding review and experimental articles about alkaloid preparations and a specific alkaloid via word and structure searches. Questions are contributed spontaneously by students, such as evaluating different reagents for enantioselectivity in 1,2-additions to aldehydes. These real-life questions engage students’ attention and are especially useful for emphasizing techniques for searching effectively. Conclusion As a result of these continuous efforts to integrate information into courses sequentially, chemistry majors acquire valuable chemical information-searching skills and knowledge and have opportunities to apply them in solving chemical problems in courses and research activities throughout their program. Graduates regularly comment on how they value the opportunities to learn about information resources relevant to each course’s assignments, built sequentially on each semester’s new skills to further augment their skills, learn to effectively select and use relevant print and electronic resources, and gain an appreciation of the role of librarians and libraries in their professional careers. Literature Cited 1. Somerville, A. N. J. Chem. Inf. Comput. Sci. 1985, 25, 314–323. 2. Somerville, A. N. J. Chem. Inf. Comput. Sci. 1990, 30, 177– 181; Carr, C. J. Chem. Educ. 1993, 70, 719–726; Carr, C. J. Chem. Educ. 2000, 77, 412–422. For more recent information, see also articles published in “The Chemical Information Instructor” feature of J. Chem. Educ., and papers presented

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by the ACS Division of Chemical Information, Abst. Pap. ACS Natl. Meetings. The workshop chemistry project involves peer-led teams, called workshops. By cooperating in small groups of six to eight students, students learn to analyze problems and reason their way to solutions. These small groups are led by undergraduate students who excelled in the course previously. To better prepare these students, they take a separate course for workshop leaders, which teaches group-facilitation techniques and provides additional chemistry depth. Originally developed for organic chemistry, the workshop program has expanded to other chemistry courses at the University of Rochester, as well as other science and non-science courses. See Gosser, D. K.; Crocolice, M. S.; Kampmeier, J. A.; Roth, V.; Strozak, V. S.; VarmaNelson, P. Peer-Led Team Learning: A Guidebook; Prentice-Hall, Inc.: Upper Saddle River, NJ, 2001; Sarquis, J. L.; Dixon, L. J.; Gosser, D. K.; Kampmeier, J. A.; Roth, V.; Strozak, V. S.; Varma-Nelson, P. The Workshop Project: Peer-Led Team Learning in Chemistry. In Student-Assisted Teaching: A Guide to Faculty-Student Teamwork; Miller, J. E., Groccia, J. E., Miller, M., Eds.; Anker Publishing Company: Bolton, MA, 2001, pp 150–155; Gosser, D. K.; Roth, V. J. Chem. Educ. 1998, 75, 185–187. Somerville, A. N.; Kende, A. S. Integrated Chemical Information Program. In Directory of Teaching Innovations in Chemistry; Meeth, L. R., Gregory, Dean S., Eds.; Studies in Higher Education, in Cooperation with the Division of Chemical Education of the American Chemical Society, 1981, p 157– 158. CRC Handbook of Chemistry and Physics, 83rd ed.; Lide, David R., Ed.; CRC Press, Inc.: Cleveland, Ohio, 2002–2003. Dictionary of Organic Compounds, 6th ed.; Buckingham, J., Macdonald, F., Eds.; Chapman & Hall: New York, 1996. Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; O’Neil, Maryadele J., Smith, Ann, Heckelman, Patricia E., Eds.; Merck & Co., Inc.: Whitehouse Station, NJ, 2001. Dean, John A. Lange’s Handbook of Chemistry, 15th ed.; McGraw-Hill: New York, 1999. Aldrich Catalog of Fine Chemical and Laboratory Equipment; Sigma-Aldrich Co.: Milwaukee, Wisconsin, 2003-2004. ChemFinder; CambridgeSoft Corporation. http:// chemfinder.cambridgesoft.com/ (accessed Feb 2003). Organic Compounds Database. http://www.colby.edu/chemistry/cmp/cmp.html (accessed Feb 2003). CRC Handbook of Tables for Organic Compound Identification, 3rd ed.; Rappoport, Zvi, Ed.; CRC Press, Inc.: Boca Raton, Florida, 1967. Utermark, Walther; Schicke, Walter. Melting Point Tables of Organic Compounds, 2nd ed.; Interscience Publishers: New York, 1963. Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C. The Systematic Identification of Organic Compounds, 7th ed.; John Wiley & Sons, Inc.: New York, 1998. Pasto, Daniel J.; Johnson, Carl R.; Miller, Marvin J. Experiments and Techniques in Organic Chemistry; Prentice-Hall: Upper Saddle River, NJ, 1992. CrossFire Beilstein, Vol. 6; MDL: San Leandro, California, 2002. See http://www.mdl.com/products/xfirebeilstein.html (accessed Feb 2003) for more information. SciFinder Scholar, 2002; Chemical Abstracts Service (CAS):



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Columbus, Ohio, 2002. See http://www.cas.org/SCIFINDER/ SCHOLAR/index.html (accessed Feb 2003) for more information. The ACS Style Guide: A Manual for Authors and Editors, 2nd ed.; Dodd, Janet S., Ed.; American Chemical Society: Washington, DC, 1997. Science Citation Index Expanded, 2002; ISI: Philadelphia, PA, 2002. See http://isi6.isiknowledge.com/portal.cgi/wos (accessed Feb 2003) for more information. Comprehensive Polymer Science: The Synthesis, Characterization, Reactions &Applications of Polymers, 1st ed.; Allen, Geoffrey, Bevington, John C., Eds.; Pergamon Press: New York, 1989. Medline via PubMed, 2002; National Library of Medicine

(NLM): Bethesda, MD, 2002. http://www.ncbi.nlm.nih.gov/ pubmed/ (accessed Feb 2003). Also, Medline via Scifinder Scholar, 2002; Chemical Abstracts Service (CAS): Columbus, Ohio, 2002. See http://www.cas.org/SCIFINDER/SCHOLAR/ index.html (accessed Feb 2003) for more information. 22. Adams, R. Organic Reactions; John Wiley & Sons: New York, 1942. 23. Larock, Richard C.; Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd ed.; WileyVCH: New York, 1999. 24. Encyclopedia of Reagents for Organic Synthesis; Paquette, Leo A., Ed.; John Wiley & Sons: New York, 1995.


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