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CHE 353
Report Format
Fall 2018
Formal report for the Bromination of Stilbene Lab
Report must be written using Microsoft word and chemdraw. Instructions for downloading
chemdraw are given on Canvas.
Font: Helvetica or Times New Roman, size 12.
Spacing: single or double.
Margins: 1” all around
Chemdraw: ACS 1996 document (File, apply document settings from) – you must draw your
own structures. (In professional settings, the ability to use MS Office, Chemdraw (and other
drawing programs), and Scifinder (or Beilstein) is considered a standard skill. You’ll not receive
training for any of these programs.)
Numbers: Which looks better? 112.3g or 112.3 g? All measured quantities should have units.
Length: Probably somewhere between five to eight pages.
Due Dates
November 14, 2018: Rough draft files, MS word and chemdraw (online submission only)
November 21, 2019: Report comments returned (or earlier)
December 3, 2018: Final draft files due (online submission only)
Key Requirements
Can the stereochemistry of the products confirm the reaction mechanism of the bromination
reaction? Your report should answer this question.
Analysis: what do the melting point and NMR spectral data tell you about the product of the
reaction? Which product(s) did you make?
Introduction: History of the bromination reaction.
Exceptional rough drafts may not require a final draft.
Formal Report Guidelines
1
Sections to be included
•
•
•
•
•
•
•
Cover Sheet
Abstract
Introduction
Materials and Methods (Experimental)
Results and Discussion
Conclusion
References
2
Cover Sheet
Joseph Egan
Fall 2015
Lab Section 355-‐01
Lab Partner: Kim Zorn
3
Abstract
•
•
•
•
The abstract is an overview of the entire experiment.
Includes the findings of the experiment
DOES NOT include speculation
Tip: do this last
Abstract1
Resveratrol was synthesized in a 4-step synthesis using a
simple Sonogashira type reaction with 93% yield using
commercially available 3,5-dimethoxy-1-ethynyl-benzene
and 4-iodoanisole, followed by reduction, isomerization,
and deprotection and with an overall yield of 63%.
1. Francisco Lara-Ochoa, Leticia C. Sandoval-Minero, Georgina Espinosa-Pérez, A new synthesis of resveratrol, Tetrahedron Letters, Volume 56, Issue 44, 28 October 2015, Pages 5977-5979, ISSN4 0040-4039,
http://dx.doi.org/10.1016/j.tetlet.2015.09.005. (http://www.sciencedirect.com/science/article/pii/S0040403915300460)
Introduction
• Background into the theory and relevance of the project
• NOT a restatement of the material provided from the pre-‐lab
“Resveratrol, a naturally occurring polyphenolic non-‐flavonoid antioxidant, is a phytoalexin
compound that has been isolated from grape skin, vine bark, nuts, berries, and many other plants.
This compound has various health benefits, including chemopreventive effects against cancer,
inflammation, aging, obesity, cardiovascular diseases, and neurodegeneration. Antioxidative,
antibacterial, and antifungal activities have also been attributed to this molecule. 1,2 A current area
of research is related to the synthesis of resveratrol oligomers which are present in many cases with
higher antioxidant properties and better activities for different types of diseases than the same
resveratrol. These new results triggered a big interest in the field, which can be appreciated for the
great number of research papers and reviews recently published.”
1. Francisco Lara-Ochoa, Leticia C. Sandoval-Minero, Georgina Espinosa-Pérez, A new synthesis of resveratrol, Tetrahedron Letters, Volume 56, Issue 44, 28 October 2015, Pages 5977-5979, ISSN5 0040-4039,
http://dx.doi.org/10.1016/j.tetlet.2015.09.005. (http://www.sciencedirect.com/science/article/pii/S0040403915300460)
Materials and Methods
• Contains information on:
• Apparatus (figure)
• Materials
• Concentrations (Ex: 3 M NaOH vs 6 M NaOH)
• Provides a detailed description of the experimental work
• Should include a biochemdraw graphic of the reaction
6
1. Francisco Lara-Ochoa, Leticia C. Sandoval-Miner o, Georgina Espinosa-Pérez, A new synthesis of resveratrol, Tetrahedron Letters, Volume 56, Issue 44, 28 October 2015, Pages 5977-5979,
ISSN
0040-4039, http://dx.doi.or g/10.1016/j.tetlet.2015.09.005. (http://www.scienc edirect.c om/sci ence/arti cle/pii/S0040403915300460)
Results and Discussion
•
•
•
•
Contains all measurements and calculations (RESULTS)
Contains DISCUSSION of what the results are and mean
Explains or attempts to explain variance and errors
Include all equations and label them
“The broad objective of these studies was to develop a more complete understanding of the
activity of an E. purpurea extract, and its constituents, on the production of cytokines and
chemokines by macrophages. To achieve this goal, we utilized the RAW 246.7 murine
macrophage-like cell line as a model, rather than primary mouse macrophages. With the use of
this cell line, it was possible assay the large number of samples produced as a result of these
experiments.”
2. Todd DA, Gulledge TV, Britton ER, Oberhofer M, Leyte-Lugo M, et al. (2015) Ethanolic Echinacea purpurea Extracts Contain a Mixture of Cytokine-Suppressive and Cytokine-Inducing Compounds, 7Including Some
That Originate from Endophytic Bacteria. PLoS ONE 10(5): e0124276. doi: 10.1371/journal.pone.0124276
Equations, Tables, Figures
Figure 1: MIC curve o f Berberine
𝐶𝐹𝑈/𝑚𝐿 =
()*+,) -./0 1.334
5 .36738 9:
Equation 1
Table IV: Extract percent inhibition
Extract
Percent Inhibition Standard Deviation
22-‐4 (20ppm)
74.76
3.00%
53-‐2 (20ppm)
65.24
2.78%
13-‐2 (20ppm)
63.14
2.59%
84-‐8 (20ppm)
58.52
6.22%
14-‐2 (20ppm)
57.13
5.78%
22-‐3 (20ppm)
53.67
7.46%
41-‐2 (20ppm)
50.13
3.10%
84-‐9 (20ppm)
49.44
6.15%
84-‐13 (20ppm)
47.32
0.54%
84-‐06 (20ppm)
41.62
0.86%
Figure 1 : The berberine curve from M arch 2 0th assay shows the M IC is around 7 5 µg/mL.
8
Generating figures
• DRAW each compound using Chembio Draw
• Label everything on a graph
•
•
•
•
Title
Axis
Units
Error bars!
9
Conclusion
• Summary of the results
• What was learned with this study
• Future studies (if applicable)
“These studies demonstrate the complexity of the modulatory effects of E. purpurea
extracts and their constituents on cytokine production by macrophage-‐like cells. It is clear
that ethanolic extracts contain multiple constituents [including alkylamides,
xanthienopyran, and others) that can suppress the production of pro-‐inflammatory
cytokines. However, these activities can be partially or completely masked by stimulatory
compounds, including [but likely not limited to) bacterial LPS.”
10Including Some
2. Todd DA, Gulledge TV, Britton ER, Oberhofer M, Leyte-Lugo M, et al. (2015) Ethanolic Echinacea purpurea Extracts Contain a Mixture of Cytokine-Suppressive and Cytokine-Inducing Compounds,
That Originate from Endophytic Bacteria. PLoS ONE 10(5): e0124276. doi: 10.1371/journal.pone.0124276
References
• The report should have instances where background information was
used. For this1, use in text references.
• Use the ACS format
•
Todd DA, Gulledge TV, Britton ER, Oberhofer M, Leyte-Lugo M, et al. (2015) Ethanolic Echinacea purpurea Extracts
Contain a Mixture of Cytokine-Suppressive and Cytokine-Inducing Compounds, Including Some That Originate from
Endophytic Bacteria. PLoS ONE 10(5): e0124276. doi: 10.1371/journal.pone.0124276
• Include the doi: ###
11
Tips for writing
• Use Microsoft WORD
• We cannot help you if you are using a software we’ve never heard of
• Write the abstract last
• Write in small bursts
• Don’t try to do it all at one time
• READ YOUR REFERENCES
• Look at how they format what they are saying
12
QUICK GUIDE: ACS CITATION STYLE
The ACS Style Guide, 3rd ed., is the standard citation style for chemistry. This Quick Guide includes the most
common formats from that publication. Examples of publication types not included in the ACS Style Guide were
created based on the most relevant examples available. If writing for publication you should also check the
“guide to authors” for the journal to which you are submitting your manuscript.
BOOKS
Several factors, such as whether a book is in a series, is cited in its entirety or only in part, has different
editions, etc. can cause variations in the citation format. These are some common formats.
Book with authors (pp 300-304)
Beall, H.; Trimbur, J. A Short Guide to Writing about Chemistry, 2nd ed.; Longman: New York, 2001; pp 17-32.
Books with editors (citing the entire book; p 302)
Editors’ names can appear in either the author (first example) or the editor position (second example).
Richey, H. G., Ed. Grignard Reagents: New Developments; John Wiley & Sons: Chicester, U.K., 2000.
Grignard Reagents: New Developments; Richey, H. G., Ed.; John Wiley & Sons: Chicester, U.K., 2000.
Chapter in an edited book (p 301)
McBrien, M. Selecting the Correct pH Value for HPLC. In HPLC Made to Measure: A Practical Handbook for
Optimization; Kromidas, S., Ed.; Wiley-VCH: Weinheim, Germany, 2006; pp 89-103.
Books in a series (p 306)
Books published in a series may be cited either as a book (first example) or as a journal (second example). If the
latter is used, then the CASSI abbreviation for the series title should also be used.
Seeber, G.; Tiedemann, B. E. F.; Raymond, K. N. In Supramolecular Chirality; Crego-Calama, M., Reinhoudt, D.
N., Eds.; Topics in Current Chemistry 265; Springer: Berlin, Germany, 2006; pp 147-183.
Seeber, G.; Tiedemann, B. E. F.; Raymond, K. N. Top. Curr. Chem. 2006, 265, 147-183.
Organic Syntheses and Inorganic Syntheses (p 305)
Cumulative volumes of Organic Syntheses are cited as books (first example); annual volumes of Organic
Syntheses and Inorganic Syntheses are often cited as journals (second example).
Organic Syntheses; Wiley & Sons: New York, 2004; Collect. Vol. No. X, pp 437-441.
Yamamoto, T. Inorg. Synth. 1989, 26, 204-207.
CONFERENCE PROCEEDINGS AND ABSTRACTS
Print full paper (pp 307-308)
Lindén, M.; Schunk, S.; Schüth, F. In Mesoporous Molecular Sieves 1998, Proceedings of the 1st International
Symposium, Baltimore, MD, July 10-12, 1998; Bonneviot, L., Béland, F., Danumah, C., Giasson, S.,
Kaliaguine, S., Eds.; Elsevier: Amsterdam, 1998; pp 45-52 (Studies in Surface Science and Catalysis, v
117).
Print abstracts of papers (p 308)
Pere, J. J. Abstracts of Papers, Part 1, 223rd National Meeting of the American Chemical Society, Orlando, FL,
Apr 7-11, 2002; American Chemical Society: Washington, DC, 2002; CELL 30.
Electronic abstracts of papers (p 323)
Costello, C. E. Development of “Biomolecule-Friendly” MS Methods. In PITTCON 2006, Orlando, FL, March
12-17, 2006 [CD-ROM]; Pittsburgh Conference on Analytical Chemistry and Applied Spectroscopy:
Pittsburgh, PA, 2007; Session 10, Paper 1.
DATA SETS
Print (pp 314-315)
TRC Spectral Data – Ultraviolet; Texas A&M University: College Station, TX, Apr 30, 1966; No. 969 (4-Methyl1-phenyl-3-tiapentane).
Data from web sites (based on pp 314-315, 320-321)
National Institute of Advanced Industrial Science and Technology. Spectral Database for Organic Compounds:
SDB; http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng, No. 2185 (1,2-ethanediol)
(accessed March 19, 2007).
Commercial databases (p324)
Reaxys, version 1.0.5968; Elsevier Properties SA: Frankfurt, Germany, 2010; Reaxys RN 2154 (1,2benzisoxazole).
SciFinder Scholar, version 2006; Chemical Abstracts Service: Columbus, OH, 2006; RN 50-78-2 (acetylsalicylic
acid).
DISSERTATIONS AND THESES
Titles of dissertations and theses are optional in print but are required in electronic format.
Print (pp 309-310)
King, K. J. Development of a Pressurized System for Oxidation Studies of Volatile Fluids. M.S. Thesis, The
Pennsylvania State University, State College, PA, March 1983.
King, K. J. M.S. Thesis, The Pennsylvania State University, State College, PA, March 1983.
Electronic (p 321)
Abrams, N. M. Efficiency Enhancement in Dye-sensitized Solar Cells through Light Manipulation. Ph.D.
Dissertation [Online], The Pennsylvania State University, University Park, PA, December 2005.
http://etda.libraries.psu.edu/theses/approved/WorldWideIndex/ETD-1061/index.html (accessed Apr 2,
2007).
ENCYCLOPEDIAS
Print (pp 305-306)
Diagnostic Reagents. Ullmann’s Encyclopedia of Industrial Chemistry, 5th ed; VCH: Weinheim, Germany,
1985; Vol. A8, pp 455-491.
Electronic (p 320)
Chelating Agents. Kirk-Othmer Encyclopedia of Chemical Technology [Online]; Wiley & Sons, Posted July 18,
2003.
http://www.mrw.interscience.wiley.com/emrw/9780471238966/kirk/article/chelhowa.a01/current/ht
ml (accessed Mar 19, 2007).
JOURNAL ARTICLES AND PREPRINTS
Journal titles use CASSI abbreviations. Commonly used CASSI abbreviations are listed in the ACS Style Guide.
Additional sources are in the Resource List at the end of this Quick Guide. Notes clarifying some aspect of the
citation may be added at the end.
Print articles (pp 291-296)
Although nice, article titles from print journals are not normally included in the citation.
Larabee, D. C.; Reynolds, T. Y.; Hochberg, R. B. Estradiol-16α-carboxylic Acid Esters as Locally Active
Estrogens. J. Med. Chem. 2001, 44, 1802-1814.
Larabee, D. C.; Reynolds, T. Y.; Hochberg, R. B. J. Med. Chem. 2001, 44, 1802-1814.
Electronic articles (pp 318-319)
The format for citing e-articles does include the article title.
Vandenabeele, P.; Edwards, H. G. M.; Moens, L. A Decade of Raman Spectroscopy in Art and Archaeology.
Chem. Rev. [Online] 2007, 107, 675-686. http://pubs.acs.org/cgibin/article.cgi/chreay/2007/107/i03/html/cr068036i.html (accessed Mar 19, 2007).
Early access articles (pp 318-319)
Padwa, A.; Bur, S. K. The Domino Way to Heterocycles. Tetrahedron [Online early access]. DOI:
10.1016/j.tet.2007.03.158. Published Online: Apr 3, 2007.
http://www.sciencedirect.com/science?_ob=PublicationURL&_tockey=%23TOC%235289%239999%239
99999999%2399999%23FLA%23&_cdi=5289&_pubType=J&view=c&_auth=y&_acct=C000014439&_vers
ion=1&_urlVersion=0&_userid=209810&md5=5c2e57fa33f1d0d201397bdd0dd2a3c4 (accessed Apr 3,
2007) (accepted manuscript, has not undergone final copyediting, typesetting, or proof review).
Padwa, A.; Bur, S. K. The Domino Way to Heterocycles. Tetrahedron [Online early access]. DOI:
10.1016/j.tet.2007.03.158. Published Online: Apr 3, 2007.
http://www.sciencedirect.com/science?_ob=PublicationURL&_tockey=%23TOC%235289%239999%239
99999999%2399999%23FLA%23&_cdi=5289&_pubType=J&view=c&_auth=y&_acct=C000014439&_vers
ion=1&_urlVersion=0&_userid=209810&md5=5c2e57fa33f1d0d201397bdd0dd2a3c4 (accessed Apr 3,
2007); accepted manuscript, has not undergone final copyediting, typesetting, or proof review.
Preprint servers (p 319)
Ranguelov, B.; Stoyanov, S. Evaporation and Growth of Crystals – Propagation of Step Density Compression
Wayves at Vicinal Surfaces. 2007, arXiv: physics/0703265. arXiv.org e-Print archive.
http://www.arxiv.org/abs/physics/0703267 (accessed Apr 3, 2007).
MATERIAL SAFETY DATA SHEETS
Relevant section in ACS Style Guide on p 315. International Chemical Safety Cards can also fit in this format,
Ethylene Glycol; MSDS No. E5125 [Online]; Mallenckrodt Baker: Phillipsburg, NJ, Feb 25, 1999.
http://www.jtbaker.com/msds/e5125.htm (accessed July 23, 2001).
Ethylene Glycol; ICSC No. 0270 (U.S. National Version) [Online]; National Institute for Occupational Safety and
Health, Centers for Disease Control and Prevention: Atlanta, GA, 2001.
http://www.cdc.gov/niosh/ipcsneng/neng0270.html (accessed July 23, 2001).
PATENTS
Include a reference to Chemical Abstracts if possible.
Print (pp 310-311)
Sarubbi, D. J.; Leone-Bay, A.; Paton, D. R. Oral Drug Delivery Compositions Comprising Modified Amino Acids
and Bioactive Peptides. U.S. Patent 5,792,451, August 11, 1998; SciFinder Scholar 1998:542693.
Electronic patent from government web site (based on pp 310-311, 320-321)
Sarubbi, D. J.; Leone-Bay, A.; Paton, D. R. Oral Drug Delivery Compositions Comprising Modified Amino Acids
and Bioactive Peptides. U.S. Patent 5,792,451, August 11, 1998. United States Patent and Trademark
Office Web site. http://patft.uspto.gov/netacgi/nphParser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G
&l=50&s1=5,958,879.PN.&OS=PN/5,958,879&RS=PN/5,958,879 (accessed Mar 23, 2007); SciFinder
Scholar 1998:542693.
Electronic patent from non-government web site (based on pp 310-311, 320-321)
Sarubbi, D. J.; Leone-Bay, A.; Paton, D. R. Oral Drug Delivery Compositions Comprising Modified Amino Acids
and Bioactive Peptides. U.S. Patent 5,792,451, August 11, 1998.
http://www.pat2pdf.org/patents/pat5792451.pdf (accessed Apr 2, 2007); SciFinder Scholar
1998:542693.
SCIFINDER SCHOLAR AND OTHER INDEXES
An author may need to cite an abstract from a source rather than the original document. When citing indexes
like SciFinder Scholar or PubMed, the citation to the original publication follows the format for that type of
publication (journal articles, patents, books, etc.) and is followed by the citation to the abstract.
Abstract from a print index (pp 298-299)
Ferch, H. Plastics, Paint Rubber 1966, 10, 85-86; Chem. Abstr., 1966, 17198g.
Abstract from electronic indexes (based on print format and pp 298-299, 318-319)
Beharry, S.; Bragg, P. D. J. Bioenerg. Biomembr. 2001, 33, 35-42; PubMed PMID=1146092.
http://www.ncbi.nlm.nih.gov/PubMed/ (accessed July 16, 2006).
Babu, V. R.; Sarath, P. S.; Karanth, N. G.; Kumar, M. A.; Thakur, M. S. Anal. Chim. Acta 2007, 582 (2), 329-334;
SciFinder Scholar AN=2006:1359559 (accessed Apr 2, 2007).
WEB SITES
Examples on pp 320-321 of the ACS Style Guide. Also see the “DATASETS” section of this Quick Guide.
Penn State Department of Chemistry. http://www.chem.psu.edu/ (accessed June 7, 2010).
Mallet Chemistry Library, University of Texas Libraries. ThermoDex Home Page: An Index of Selected
Thermodynamic and Physical Property Resources. http://www.lib.utexas.edu/thermodex/ (accessed
Mar 19, 2007).
NOTES
Journal abbreviations
Chemists use standard abbreviations for journal titles and the names of conference proceedings. These are
published in CASSI, the Chemical Abstracts Service Source Index.
Personal names
Personal names often cause difficulties when preparing bibliographies or reference lists. Many western
European names are arranged with the given name first and the family name last, so that in a bibliography the
family name would come first, followed by a comma and then the given name (or initial).
Not all western European names follow this pattern, and names of authors from other parts of the world
certainly do not. The Chicago Manual of Style has an excellent discussion of the rules for personal names
(sections 8.5-8.20) and alphabetizing (sections 18.69-18.87).
RESOURCE LIST
The ACS Style Guide: Effective Communication of Scientific Information, 3rd ed. Coghill, A.M.; Garson, L.R., Eds.
American Chemical Society: Washington, DC; Oxford University Press: Oxford, U.K., New York, 2006. (Chapter 14
is available online at http://pubs.acs.org/userimages/ContentEditor/1246030496632/chapter14.pdf).
CASSI—Chemical Abstracts Service Source Index: 1907-1999 Cumulative. Chemical Abstracts Service: Columbus,
OH, 2000 (and supplements). (A basic online version of CASSI is available at http://cassi.cas.org/search.jsp;
another good source for journal abbreviations is http://www.library.ubc.ca/scieng/coden.html).
The Chicago Manual of Style, 15th ed.; University of Chicago Press: Chicago, IL, 2003.
This publication is available in alternative media on request.
Penn State is committed to affirmative action, equal opportunity, and the diversity of its workforce.
ACS Style/rev. June 2010/njb2
CHE-353-STILBENE_DIBROMIDE
0.80
0.75
0.70
0.65
0.60
0.55
0.50
0.45
0.40
0.35
0.30
0.25
3 unique shifts
0.20
0.15
0.10
0.05
0.00
-0.05
220
210
200
190
180
170
160
150
140
130
120
110
100
90
f1 (ppm)
80
70
60
50
40
30
20
10
0
-10
-20
13
CHE-353-STILBENE_DIBROMIDE
12
11
10
9
8
7
6
CHCl3 (NMR Solvent)
5
Multiplet, 6
4
3
Singlet, 2
2
Doublet, 4
1
10.0
9.5
9.0
8.5
8.0
7.5
1.93
4.00
5.89
0
7.0
6.5
6.0
5.5
-1
5.0
4.5
f1 (ppm)
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5