1. A Wiki-Based Chemical Information Instructional Resource Gary Wiggins Indiana University School of Informatics wiggins@indiana.edu May 21, 2007

2. Abstract In 1991, McGraw-Hill published the book Chemical Information Sources, an at-the- time innovative textbook that included a disk with a database containing citations to 2500 reference materials and the software to search it. The database was later converted to a Web-searchable format, the Chemical Reference Sources Database, and the lecture notes for the undergraduate Chemical Information Sources class were placed on the Web. In 2006, all instructional modules associated with the course were converted to the Wiki format, thus allowing others to contribute to the material. Wikis are also used for some courses in the IU School of Informatics graduate cheminformatics degree and certificate programs, e.g., Chemical Information Technology and Programming for Science Informatics. The Chemical Information Sources Wiki has 20 modules covering everything from how to find a method of synthesizing a compound to how to find a job. The tool is integrated with a related Wiki source, SIRCh, Selected Internet Resources for Chemistry, and other Web resources. In addition, links are provided to relevant sections of the Clearinghouse for Chemical Information Instructional Materials where additional materials that are designed to instruct people in the use of chemical reference tools can be found. Experiences in creating and maintaining the Wiki resource in a shared- author, open-access environment will be presented.

3. Huge Size of the Chemical Lit ~ 50 million chemical substances ~ 6 million reagents ~ 7 million published reactions ~16,000 protein crystal structures ~250,000 small molecule x-ray structures --Robert Glen and Susan Aldridge (2002) http://xlink.rsc.org/?DOI=b207793k

4. ACS CPT Statements on Chemical Information Retrieval A student who intends to become a practicing chemist, or who will use chemistry in allied fields of science and medicine, should know how to use the chemical literature effectively and efficiently. (2003) Students should be able to use the peer-reviewed scientific literature effectively and evaluate technical articles critically. They should learn how to retrieve specific information from the chemical literature, including the use of Chemical Abstracts and other compilations, with online, interactive database-searching tools. (2007 draft)

5. 2003 CPT Recommendations on How to Gain Proficiency Proficiency in chemical information retrieval should be acquired through formal instruction. –Through a course dedicated to the subject of chemical information retrieval, –Through integration into other chemistry courses, –Through coordination and monitoring of each student's satisfactory achievement, preferably by one faculty member or librarian.

6. 2007 Draft CPT Recommendations on How to Gain Proficiency Approved programs must provide instruction on the effective retrieval and use of the chemical literature. –A specific course is an excellent means of imparting information-retrieval skills, though such a course usually would not qualify as an in-depth course. 37% used this option in 2005. –Integrating the use of these skills into several individual courses is also an effective approach. 73% used this option in 2005. –Both library and online exercises should be a part of such instruction.

7. Little Red Book A good idea with the wrong info technology.

8. Whats a Wiki? A website that allows visitors to add, remove, and edit content A collaborative technology for organizing information on Web sites Wikis allow for linking among any number of pages. The ease of interaction and operation makes a wiki an effective tool for mass collaborative authoring. Source: Wikipedia, 5/17/2007

9. Graduate Cheminformatics Courses Taught with a Wiki I571 Chemical Information Technology –http://cheminfo.informatics.indiana.edu/djwild/I571_20 06_wiki/index.php/Main_Page I573 Programming for Science Informatics –http://cheminfo.informatics.indiana.edu/djwild/I573_20 07_wiki/index.php/Main_Page

10. Chemical Information Sources Wiki http://cheminfo.informatics.indiana.edu/cic c/cis/index.php/Main_Page Purposes: –To provide a free guide to the many sources of reference materials available to those with questions related to chemistry –To provide a convenient text to supplement instruction in chemical information retrieval Historical Roots: the C471 Chemical Information Sources course taught from 1976-2003 in the IU Chemistry Department

11. Overall Organization of the CIS Wiki How and Where to Start How and Where to Search: General How and Where to Search: Specialized Sources Communication in Chemistry Miscellaneous

12. How and Where to Start 1. The Publication Process: Primary, Secondary, and Tertiary Sources 2. Guides to Chemical Information Sources and Databases 3. General Information on Computer Searching 4. Current Awareness, Reviews, and Document Delivery 5. Background Reading: Dictionaries, Encyclopedias, and Other Books

13. Books

14. Screen Shot 1

15. How and Where to Search: General 6. Searching by Author or Organization Name and by Known Citations 7. Searching by Subject 8. Chemical Name and Formula Searching 9. Structure Searching

16. Example 2

17. How and Where to Search: Specialized Sources 10. Searching for the Synthesis or Reactions of Specific Compounds or Classes of Compounds 11. Chemical Safety and Toxicology Information 12. Analytical Chemistry 13. Physical Property Information 14. Chemical Patent Searching

18. Beilstein 1

19. Communication in Chemistry 15. Chemistry Newsgroups, Discussion Lists, and Blogs 16. Molecular Visualization Tools and Sites 17. Science Writing Aids

20. ChemDraw Example

21. Miscellaneous 18. Chemical History, Biography, Directories, and Industry Sources 19. Teaching and Study of Chemistry 20. Careers in Chemistry

22. Teaching

23. Usage of the CIS Wiki Visitors since January 1, 2007 (as of 5/17/07) –Range from 1235 (Background Reading) to 10,700 (Chemical Name and Formula Searching) –Average number of visits per page: 3263

24. Other CIS Wiki Features SIRCh: Selected Internet Resources for Chemistry –http://cheminfo.informatics.indiana.edu/cicc/ci s/index.php/SIRCh:_Selected_Internet_Resou rces_for_Chemistry CRSD: Chemical Reference Sources Database –http://www.oscar.chem.indiana.edu/cfdocs/lib chem/crsd/crsdintro.html

25. SIRCh

26. CRSD Search

27. Parting words... If you're not part of the solution, you're part of the precipitate!

28. Moving on to retirement

29. Bibliography ACS Committee on Professional Training. Chemical Information Retrieval. http://www.chemistry.org/portal/Chemistry?PID=acsdisplay.html&DOC=edu cation\cpt\ts_cheminfo.html http://www.chemistry.org/portal/Chemistry?PID=acsdisplay.html&DOC=edu cation\cpt\ts_cheminfo.html ACS Committee on Professional Training. Undergraduate Professional Education in Chemistry: Guidelines and Evaluation Procedures. Draft, 2/27/2007. http://acswebcontent.acs.org/education/cpt/acs_draftguidelines.pdf http://acswebcontent.acs.org/education/cpt/acs_draftguidelines.pdf Culp, F. Bartow. "Ten or so things that every chemistry librarian absolutely, positively has to have to keep from being an absolute plonk." Sci-Tech News, February 2004, 58(1), 9. also published as: SLA Chemistry Division E-Newsletter Winter 2004, 18(3), 19-20). http://www.sla.org/division/dche/Newsletters/Feb_2004.pdf http://www.sla.org/division/dche/Newsletters/Feb_2004.pdf Garritano, Jeremy R.; Culp, F. Bartow. Chemical information instruction, 1984-2004: who is leading the charge? Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, United States, March 13-17, 2005 (2005), CINF-107. Also found at: http://units.sla.org/division/dche/2005/garritano.pdf http://units.sla.org/division/dche/2005/garritano.pdf Gasaway, Laura. The open archives movement. Information Outlook October 2004, 8(10), 36, 39-40.

30. Bibliography Glen, Robert; Aldridge, Susan. Developing tools and standards in molecular informatics. Chemical Communications 2002, (23), 2745- 2747. DOI: 10.1039/b207793k http://xlink.rsc.org/?DOI=b207793khttp://xlink.rsc.org/?DOI=b207793k Huber, C.; Porter, K. Cheap tricks. http://www.indiana.edu/~cheminfo/workshop/cheap.html http://www.indiana.edu/~cheminfo/workshop/cheap.html McLeland, Le-Nhung. What every chemist should know about patents. http://www.chemistry.org/portal/resources/?id=1b41692a6cf811d6f8 dd6ed9fe800100 http://www.chemistry.org/portal/resources/?id=1b41692a6cf811d6f8 dd6ed9fe800100 Murray-Rust, Peter; Rzepa, Henry S.; Tyrrell, Simon M.; Zhang, Yong. Representation and use of chemistry in the global electronic age. Organic & Biomolecular Chemistry 2004, 2(22), 3192-3203 (correction: 2005, 3(10), 2037). Somerville, Arleen N.. Chemical Information Instruction in Academe: Recent and Current Trends. Journal of Chemical Information and Computer Sciences 1998, 38(6), 1024-1030.

31. Bibliography Wagner, A. Ben. "Finding physical properties of chemicals: A practical guide for scientists, engineers, and librarians. Science & Technology Libraries 2001, 21(3/4), 27-45. (published Fall 2003) Text for personal and professional use available at: http://ublib.buffalo.edu/libraries/asl/staff/documents/wagner_phys_pr op_stl_art.pdf http://ublib.buffalo.edu/libraries/asl/staff/documents/wagner_phys_pr op_stl_art.pdf Wiggins, Gary. Overview of databases/data sources. in Gasteiger, Johannes, ed. Handbook of Chemoinformatics: From Data to Knowledge in 4 Volumes. Wiley-VCH: 2003, v. 2, pp. 496-506. http://www.indiana.edu/~cheminfo/C571/wiggins_chapter_2003.pdf http://www.indiana.edu/~cheminfo/C571/wiggins_chapter_2003.pdf Wiggins, Gary. Teaching chemical literature, databases, and chemical informatics. CPT; Committee on Professional Training [newsletter] Spring 2004, 4(1), 1-2. http://acswebcontent.acs.org/PDF/cpt/nl_cpt_spring2004.pdf http://acswebcontent.acs.org/PDF/cpt/nl_cpt_spring2004.pdf