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Journal Articles: 34 results
Synthesis Explorer: A Chemical Reaction Tutorial System for Organic Synthesis Design and Mechanism Prediction  Jonathan H. Chen and Pierre Baldi
Synthesis Explorer is an interactive tutorial system for organic chemistry that enables students to learn chemical reactions in ways previously unrealized. Pedagogical experiments in undergraduate classes at UC Irvine indicate that the system can improve average student examination performance by ~10%.
Chen, Jonathan H.; Baldi, Pierre. J. Chem. Educ. 2008, 85, 1699.
Mechanisms of Reactions |
Reactions |
Synthesis
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory  Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry.
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory  Jacqueline Bennett, Kristen Meldi, and Christopher Kimmell II
In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) alpha-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.
Bennett, Jacqueline; Meldi, Kristen; Kimmell, Christopher, II. J. Chem. Educ. 2006, 83, 1221.
Aldehydes / Ketones |
Gas Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
The Amazingly Versatile Titanocene Derivatives  Donald C. Bowman
Derivatives of titanocene are remarkably versatile in their chemical applications. This article presents a brief review of the derivatives' uses in the fields of polymers, medical oncology, and organic synthesis.
Bowman, Donald C. J. Chem. Educ. 2006, 83, 735.
Applications of Chemistry |
Catalysis |
Drugs / Pharmaceuticals |
Organometallics |
Polymerization |
Synthesis
The Discovery and Development of Cisplatin  Rebecca A. Alderden, Matthew D. Hall, and Trevor W. Hambley
Cisplatin is currently one of the most widely used anticancer drugs in the world. The unlikely events surrounding the discovery of its anticancer activity, subsequent introduction into the clinic, and the continuing research into platinum compounds is the subject of this review.
Alderden, Rebecca A.; Hall, Matthew D.; Hambley, Trevor W. J. Chem. Educ. 2006, 83, 728.
Bioinorganic Chemistry |
Coordination Compounds |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Metallic Bonding |
Oxidation State |
Synthesis
Glycosyltransferases A and B: Four Critical Amino Acids Determine Blood Type  Natisha L. Rose, Monica M. Palcic, and Stephen V. Evans
Human A, B, and O blood type is determined by the presence or absence of distinct carbohydrate structures on red blood cells. In this review the chemistry of the blood group ABO system and the role of glycosyltransferase A, glycosyltransferase B, and the four amino acids critical to determining blood group status are discussed.
Rose, Natisha L.; Palcic, Monica M.; Evans, Stephen V. J. Chem. Educ. 2005, 82, 1846.
Carbohydrates |
Enzymes |
Kinetics |
Bioorganic Chemistry |
Crystals / Crystallography |
Molecular Biology |
X-ray Crystallography |
Amino Acids
Cotton Effect in Copper–Proline Complexes in the Visible Region  Victor Volkov and Rolf Pfister
This article suggests taking advantage of the visible dd electronic transition of Cu2+, which allows one to contrast the normal optical rotatory dispersion response of d- and l-proline in aqueous solution with the strong Cotton effect observed when these amino acids are complexed with a metal cation.
Volkov, Victor; Pfister, Rolf. J. Chem. Educ. 2005, 82, 1663.
Chirality / Optical Activity |
IR Spectroscopy |
Molecular Properties / Structure |
Spectroscopy |
Stereochemistry |
UV-Vis Spectroscopy |
Amino Acids |
Coordination Compounds |
Crystal Field / Ligand Field Theory
A Green Polymerization of Aspartic Acid for the Undergraduate Organic Laboratory  George D. Bennett
Based on a technology that won a Presidential Green Chemistry Challenge Award, this experiment involves the thermal polymerization of aspartic acid and subsequent hydrolysis to give sodium poly(aspartate). The procedure is suitable for introducing students to the important topic of polymers and for illustrating several of the principles of green chemistry.
Bennett, George D. J. Chem. Educ. 2005, 82, 1380.
Green Chemistry |
Synthesis |
Industrial Chemistry |
Natural Products |
Polymerization |
Proteins / Peptides
The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids  Addison Ault
Examples of the industrial synthesis of pure amino acids are presented. The emphasis is on the synthesis of (S)-glutamic acid and, to a lesser extent, (S)-lysine and (R,S)-methionine. These amino acids account for about 90% of the total world production of amino acids.
Ault, Addison. J. Chem. Educ. 2004, 81, 347.
Amino Acids |
Biotechnology |
Chirality / Optical Activity |
Consumer Chemistry |
Enzymes |
Natural Products |
Stereochemistry |
Synthesis |
Food Science
Protein Design Using Unnatural Amino Acids  Basar Bilgiçer and Krishna Kumar
Using examples from the literature, this article describes the available methods for unnatural amino acid incorporation and highlights some recent applications including the design of hyperstable protein folds.
Bilgiçer, Basar; Kumar, Krishna. J. Chem. Educ. 2003, 80, 1275.
Amino Acids |
Bioorganic Chemistry |
Biotechnology |
Proteins / Peptides |
Synthesis |
Molecular Properties / Structure
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
Dendrimers: Branching Out of Polymer Chemistry  Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
Imidazole and Benzimidazole Synthesis (M. Ross Grimmett)  Paul G. Rasmussen
A useful reference for possible student experiments, starting materials for projects, and general information about heterocyclic ring construction.
Rasmussen, Paul G. J. Chem. Educ. 1999, 76, 1345.
Synthesis |
Heterocycles
The Art and Science of Organic and Natural Products Synthesis  K. C. Nicolaou, E. J. Sorensen, and N. Winssinger
In this article, the history of the art and science of organic and natural products synthesis is briefly reviewed and the state of the art is discussed. The impact of this discipline on biology and medicine is amply demonstrated with examples, and projections for future developments in the field are made.
Nicolaou, K. C.; Sorensen, E. J.; Winssinger, N. J. Chem. Educ. 1998, 75, 1225.
Natural Products |
Synthesis |
Medicinal Chemistry |
Applications of Chemistry |
Drugs / Pharmaceuticals
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis  Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
On the Formation of Peptide Bonds  Stojanoski, Kiro; Zdravkovski, Zoran
In an attempt to simplify the concept of peptide bond formation, many textbooks misrepresent the energy requirement that is necessary for peptide bonds to form.
Stojanoski, Kiro; Zdravkovski, Zoran J. Chem. Educ. 1993, 70, 134.
Amino Acids |
Biosynthesis |
Equilibrium |
Bioenergetics
The malonic ester synthesis in the undergraduate laboratory  Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D.
The versatile reactions of diethyl malonate represent an important lecture topic in introductory organic courses, but are only rarely performed in the lab because of several problems associated with performing these reactions. These authors present a lab the circumvents some of the typical problems.
Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D. J. Chem. Educ. 1991, 68, 689.
Aromatic Compounds |
Aldehydes / Ketones |
Amino Acids |
Heterocycles |
Amides
Oxidation of cysteine to cystine using hydrogen peroxide  Hill, John W.; Coy, Robert B.; Lewandowski, Peter E.
This synthesis has several advantages as an undergraduate laboratory exercise.
Hill, John W.; Coy, Robert B.; Lewandowski, Peter E. J. Chem. Educ. 1990, 67, 172.
Amino Acids |
Oxidation / Reduction
Synthesis of an enkephalinase inhibitor, Gly-Gly-Phe-Leu, by continuous-flow peptide synthesizer  Iskander, Magdy N.; Jones, Paul A.
The assembly of the continuous flow peptide synthesizer was carried out in the author's laboratory with no difficulty and has generated great interest among their students.
Iskander, Magdy N.; Jones, Paul A. J. Chem. Educ. 1990, 67, 170.
Synthesis |
Proteins / Peptides |
Medicinal Chemistry |
Laboratory Equipment / Apparatus
Microscale synthesis and analysis of a dipeptide  Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji
The synthesis of a dipeptide from its component amino acids and its analysis by chiral-phase thin-layer chromatography.
Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji J. Chem. Educ. 1989, 66, 965.
Microscale Lab |
Synthesis |
Proteins / Peptides |
Thin Layer Chromatography |
Amino Acids
Azosulfonamides: Preparation and binding to carbonic anhydrase: A bioorganic chemistry experiment  Manalang, Mary G.; Bundy, Hallie F.
Preparation of azosulfonamide, visible absorption analysis of free and enzyme-bond azosulfonamide, and titration of BCA with azosulfonamide.
Manalang, Mary G.; Bundy, Hallie F. J. Chem. Educ. 1989, 66, 609.
Bioorganic Chemistry |
Synthesis |
Proteins / Peptides |
Titration / Volumetric Analysis |
Enzymes
A convenient synthesis of aspartame  Lindeberg, Gunnar
The one tube, enzymatic synthesis of the dipeptide sweetener aspartame.
Lindeberg, Gunnar J. Chem. Educ. 1987, 64, 1062.
Synthesis |
Enzymes |
Proteins / Peptides
A project lab for an advanced general chemistry course featuring the amino acid, glycine  Dudek, Emily P.
Synthesis of glycine, measurement of its nitrogen content by eudiometry, and the estimation of its Rf value as compared to other amino acids using paper chromatography.
Dudek, Emily P. J. Chem. Educ. 1987, 64, 899.
Amino Acids |
Synthesis
The use of fluoromethanes in organic synthesis  Everett, T. Stephen
A review of advances in selective fluorination; mechanisms and applications of fluoromethanes in organic synthesis.
Everett, T. Stephen J. Chem. Educ. 1987, 64, 143.
Synthesis |
Mechanisms of Reactions
The enzymatic resolution of aromatic amino acids  Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D.
This article presents an experiment that can demonstrate as many principles of steroisomersim as possible and is also efficient in terms of time and preparation.
Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Aromatic Compounds |
Amino Acids |
Enzymes
The synthesis of a dipeptide from its component amino acids: Protecting groups in the elementary organic laboratory  Young, Paul E.; Campbell, Andrew
A three-step procedure for synthesizing a dipeptide from its component amino acids.
Young, Paul E.; Campbell, Andrew J. Chem. Educ. 1982, 59, 701.
Synthesis |
Amino Acids |
Proteins / Peptides
A photochemical preparation of indoles: An organic chemistry experiment  Kane, Victoria; Schultz, Arthur G.
Modification of a research-oriented photochemical experiment the provides an early exposure to the synthetic advantages of organic photochemistry and illustrates the formation of a mechanistically interesting carbon-carbon bond.
Kane, Victoria; Schultz, Arthur G. J. Chem. Educ. 1979, 56, 555.
Synthesis |
Photochemistry
A synthesis of o-chlorocinnamic acid utilizing a Meerwein reaction. An undergraduate organic experiment  Cleland, George H.
The authors share an experimental procedure that converts an o-chloroaniline to o-chlorocinnamic acid.
Cleland, George H. J. Chem. Educ. 1978, 55, 814.
Carboxylic Acids |
Synthesis
Non-covalent interactions: Key to biological flexibility and specificity  Frieden, Earl
Summarizes the types of non-covalent interactions found among biomolecules and how they facilitate the function of antibodies, hormones, and hemoglobin.
Frieden, Earl J. Chem. Educ. 1975, 52, 754.
Noncovalent Interactions |
Hydrogen Bonding |
Water / Water Chemistry |
Proteins / Peptides |
Amino Acids |
Molecular Properties / Structure |
Hormones
Questions [and] Answers  Campbell, J. A.
184-187. Four chemistry questions and their answers.
Campbell, J. A. J. Chem. Educ. 1975, 52, 327.
Enrichment / Review Materials |
Metabolism |
Gases |
Amino Acids
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
Preparation of the members of an homologous series: An organic chemistry experiment  Kolenbrander, Harold M.
This article describes an experiment involving the synthesis of S-alkyl derivatives of homocysteine.
Kolenbrander, Harold M. J. Chem. Educ. 1970, 47, 56.
Synthesis |
Molecular Properties / Structure |
Alkylation