Beilstein Commander, SciFinder
Scholar, and Google
Lyle Isaacs
Department of Chemistry and Biochemistry
University of Maryland College Park
MY TEACHING PHILOSOPHY / GOALS
• Faculty members should act as seasoned guides to teach students
how to ask their own scientific questions, how to answer them using
current tools, and how to communicate the results.
• Teaching through research.
• Show students how a practicing organic chemist thinks.
• When I started at the University of Maryland I was struck by the
disconnect between the way I learn and the way we teach.
• Reasoning by analogy, rules of thumb, etc.
• The use of online databases as self-teaching tools was
non-existent.
• Given that I have room for only a couple of students in my laboratory
per semester, how can I engage the majority of students in “learning
through research”?
• 2-minute essays
• Group problem solving
• Online databases as a powerful self-teaching tool.
CHEMISTRY 247 ASSIGNMENTS
• Chemistry 247 is second semester organic chemistry for majors.
• Four Online Exercises at 17.5 points each (out of 1000 total)
• Investigate the generality of the Williamson ether synthesis
• Compare and contrast the ease of obtaining information regarding
cucurbituril using SciFinder, Beilstein, and Google.
• Devise a cocaine synthesis from commercially available materials.
• Explore the generality of your favorite carbonyl condensation
reaction from Ch. 23 of McMurry.
• Final Paper (100 points)
• Must ask a scientific question and use either SciFinder or Beilstein
to answer that question.
SEARCHING WITH SCIFINDER
COMPARE AND CONTRAST GOOGLE, SCIFINDER,
AND BEILSTEIN
In this exercise you should search for chemical information regarding cocaine
using the 3 search tools.
1) What is the structure of cocaine?
2) How is it synthesized?
3) What are the physiological effects of cocaine?
4) Compare and contrast the ease / difficulty of actually using each search tool.
5) Comment on the relative quality of the search results obtained by each search
engine (e.g. are they up-to-date, are they relevant, is the information
accurate, etc.).
6) Which search engine is most appropriate for gathering chemical information?
A SELECTION OF STUDENT PAPER TOPICS
(what happened to rock and roll?)
• Viagra: How is sildenafil synthesized
and how does it work?
O
N
EtO HN
N
Pr
O S
N
O
O
N
• A Synthesis of Lysergic Acid
O
O
Viagra
O
O
O
• The Drugs Behind Lethal Injection
• Chemical structure and synthesis
of Silly Putty.
NH
CH3
S
NH
H
• The Effects of Mustard Gas
O
Pentothal
(-)-a-thujone
(in absinthe)
O
O
n
Polyethylene terephthalate
(PET)
• Total Synthesis of (-)-a-Thujone
• Synthesis of polyesters
Cl
mustard gas
N
• The action of pheromones in a
honey bee colony
S
Cl
O
OH
(From queen
mandibular
pheromone)
GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS
1. How did you approach researching a
chemical problem before the semester
started?
2. How would you go about researching
a chemical problem in the future?
3. Was the amount of time invested in
the online database exercises
commensurate with the amount of
learning that took place?
Google/
Internet
Text / TA
Prof / Lib.
SciFinder
alone
SciFinder
+ Internet
73
27
0
0
3
9
21
68
Yes
Maybe
No
70
17
13
GOOGLE / SCIFINDER / BEILSTEIN EVALUATIONS
1. The instructor adequately explained how to use the online databases
for the exercises in this course.
2. The exercises helped me see the generalities of organic chemistry
rather than focus on the differences.
3. I learned how to use the online databases to ask and answer my own
chemical questions.
4. The online database exercises were a worthwhile addition to this
course.
5. The exercises made me more aware of the need to evaluate the
relevancy of information obtained from online databases.
6. I am better able to distinguish between a question that is likely to have
a clear-cut answer from one that is vague.
7. In the future I will use Google to help answer my chemical questions?
8. In the future I will use SciFinder to help answer my chemical
questions?
9. In the future I will use Beilstein to help answer my chemical questions?
10. The online database exercises helped me see how a practicing
organic chemist actually thinks.
STRONGLY
AGREE
Q#
1
2
3
4
5
6
7
8
9
10
A
60
33
48
41
45
46
40
45
22
36
B
33
33
38
38
28
40
30
31
30
44
STRONGLY
DISAGREE
C D
5
2
28 6
14
13 8
18 9
15
20 8
17 5
35 11
10 8
E
2
2
2
2
A SELECTION OF STUDENT EVALUATION COMMENTS
• “The course gave me a better understanding of chemistry and allowed
me to better relate it to everyday life.”
• “He asked questions of the class and allowed us to discuss them amongst
ourselves rather than just telling us the answer. I think that was great.”
• “Dr. Isaacs would ask for 2 minute essays at the end of class that he
would address at the beginning of the next class to be sure everyone got
the concepts. I’ve found it very innovative and helpful.
• “There weren’t really any weakness except maybe Beilstein.” “Before I
only used the internet, but I appreciate SciFinder more now at the end of
the semester.” “The databases help you see info that is out there. It’s
overwhelming! But, you can also see the unanswered questions. That was
the most important part for me.”
THINGS FOR THE FUTURE
• Drop Beilstein and focus on SciFinder and other databases / computer
based tools?
• $$ Issues with number of Scifinder seats.
• Web of science, Online journals, etc.?
• ChemDraw (nomenclature / NMR), molecular modeling?
• Develop methods that would allow these exercises to be conducted
In a large (≈ 250 person) lecture course.
• Must modify goals for the non-majors audience
• Improve the exit questionaire and develop an entrance questionaire
that could be used to better quantify student progress.
• Develop methods to have interaction between students as part of the
online databases exercises.
• Disseminate results if warranted.
ACKNOWLEDGEMENTS
• My Chemistry 247 who
cheerfully participated in the
experiments described in
this talk!
• The Isaacs group for
keeping the laboratory
research rolling along.
Funding
NIH (GM61854)
University of Maryland