| Journal Articles: 25 results |
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Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry Laboratory Linda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. Chen
Describes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.
Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ. 2007, 84, 1992.
Amines / Ammonium Compounds |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
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Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions James V. McCullagh and Kelly A. Daggett
In this experiment, electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B) using common equipment while avoiding often troublesome, hydroscopic Lewis acids. Subsequent UVvis analysis produce spectra that match commercially available dye samples.
McCullagh, James V.; Daggett, Kelly A. J. Chem. Educ. 2007, 84, 1799.
Acids / Bases |
Aromatic Compounds |
Dyes / Pigments |
Electrophilic Substitution |
Equilibrium |
Synthesis |
UV-Vis Spectroscopy
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Chemical Aspects of Local and Regional Anesthesia Robert Brunsvold and Daryl L. Ostercamp
The chemistry that underlies the development of local and regional anesthesia is explored. Emphasis is placed upon the importance of acidity constants and lipophilic versus hydrophilic character in interpreting what affect a particular compound has upon biological processes.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1816.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
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Presumptive and Confirmatory Drug Tests Craig Anderson
Tests for illegal drugs were performed on unknowns obtained from over-the-counter cold medicines. Substances that tested positive for the qualitative Marquis color test were found to be false positives for illegal substances, while scopolamine hydrochloride shows a false positive for cocaine hydrochloride with the cobalt thiocyanate reagent.
Anderson, Craig. J. Chem. Educ. 2005, 82, 1809.
Drugs / Pharmaceuticals |
Qualitative Analysis |
Acids / Bases |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry
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Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies Jeffrey I. Seeman
The HendersonHasselbalch equation calculates the equilibrium distribution of 50:50 for nicotine in its nonprotonated (free base form), relative to its monoprotonated form, at pH of 8 in dilute aqueous solution. This ratio has then been used in the literature to predict the effect of ammonia compounds in tobacco and in smoke on nicotine pyrolysis and smoke chemistry. Experiments demonstrate that neither the thermal chemistry of tobacco alkaloids nor the transfer of nicotine from tobacco to smoke can be explained by the position of the nonprotonated versus monoprotonated form equilibrium in aqueous extracts of tobacco. The high thermal stability of nicotine in air allows nicotine salts to be converted to nonprotonated nicotine and volatilize during heating prior to any substantial decomposition of the nicotine moiety. In contrast, cocaine hydrochloride is thermally unstable and will rapidly decompose upon heating; cocaine hydrochloride must first be converted to its nonprotonated form prior to heating and volatilization.
Seeman, Jeffrey I. J. Chem. Educ. 2005, 82, 1577.
Acids / Bases |
Applications of Chemistry |
Calorimetry / Thermochemistry |
Heterocycles |
pH |
Natural Products |
Gases
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Enantiomeric Resolution of (±)-Mandelic Acid by (1R,2S)-(–)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism Marsha R. Baar and Andrea L. Cerrone-Szakal
There has been an increasing need, particularly in the pharmaceutical industry, to prepare chiral substances in single-isomer form. A chiral technique that makes an excellent introductory organic chemistry experiment is enantiomeric resolution. The classical resolution of ()-mandelic acid using the chiral amine, (1R,2S)-()-ephedrine, was adapted for use in introductory organic chemistry lab curricula.
Baar, Marsha R.; Cerrone-Szakal, Andrea L. J. Chem. Educ. 2005, 82, 1040.
Acids / Bases |
Chirality / Optical Activity |
Separation Science |
Stereochemistry |
Diastereomers |
Enantiomers
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Lewis Acid–Base, Molecular Modeling, and Isotopic Labeling in a Sophomore Inorganic Chemistry Laboratory Chip Nataro, Michelle A. Ferguson, Katherine M. Bocage, Brian J. Hess, Vincent J. Ross, and Daniel T. Swarr
Computational methods can be introduced to simulate IR spectra and to view the HOMO of the Lewis base and the LUMO of the Lewis acid. In addition to the computational exercise, NaBD4 can be used in the synthesis of the adduct in place of NaBH4. This allows the students to observe the effect of isotopic labeling on IR spectra.
Nataro, Chip; Ferguson, Michelle A.; Bocage, Katherine M.; Hess, Brian J.; Ross, Vincent J.; Swarr, Daniel T. J. Chem. Educ. 2004, 81, 722.
Lewis Acids / Bases |
Molecular Modeling |
Isotopes |
IR Spectroscopy |
Laboratory Computing / Interfacing
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Simulating How a Virus Spreads through a Population: An Introduction to Acid-Base Chemistry in the Organic Chemistry Laboratory Ronald M. Jarret
The traditional lab exercise that achieves separation of a mixture of 4-aminoacetophenone and benzoic acid by chemically active extraction has been expanded to include an exercise that uses materials from the extraction experiment to simulate how a virus spreads through a population.
Jarret, Ronald M. J. Chem. Educ. 2001, 78, 525.
Acids / Bases |
Separation Science |
Solutions / Solvents |
Aromatic Compounds |
Carboxylic Acids
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Thermochromism in Commercial Products Mary Anne White and Monique LeBlanc
Many commercial products change color with a change of temperature. How do they do it? The processes responsible for the two major categories of commercial thermochromic coloring agents are presented, along with a description of applications of thermochromic materials.
White, Mary Anne; LeBlanc, Monique. J. Chem. Educ. 1999, 76, 1201.
Acids / Bases |
Consumer Chemistry |
Materials Science |
Applications of Chemistry
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Comments on the Treatment of Aromaticity and Acid-Base Character of Pyridine and Pyrrole in Contemporary Organic Chemistry Textbooks Hugh J. Anderson and Ludwig Bauer
Presentations of aromaticity and acid-base character of pyridine and pyrrole in 18 contemporary organic chemistry textbooks were surveyed.
Anderson, Hugh J.; Bauer, Ludwig. J. Chem. Educ. 1999, 76, 1151.
Acids / Bases |
Aromatic Compounds
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What Is the Geometry at Trigonal Nitrogen? K. P. Sudlow and A. A. Woolf
The geometry of trigonal nitrogen is discussed from VSEPR, crystallographic, and computational studies. The VSEPR theory is valid unless hydrogen bonding is strong enough or dispersal of nitrogen lone pair density is possible over receptive groups.
Sudlow, K. P.; Woolf, A. A. J. Chem. Educ. 1998, 75, 108.
Learning Theories |
Molecular Properties / Structure |
Crystals / Crystallography |
Computational Chemistry |
VSEPR Theory |
Hydrogen Bonding |
Amines / Ammonium Compounds
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"Crack" - A High-Interest Compound Illustrating Important Concepts in General Chemistry Hoyt, William
Using crack and cocaine as examples of amine acid-base chemistry.
Hoyt, William J. Chem. Educ. 1995, 72, 322.
Acids / Bases |
Enrichment / Review Materials |
Amines / Ammonium Compounds |
Esters
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The Determination of "Apparent" pKa's: Part II. An Experiment Using Very Weak Acids (pKa's > 11.4) Cawley, John J.
Experimental procedure for illustrating when the Henderson-Hasselbalch equation fails for very weak acids; data and analysis included.
Cawley, John J. J. Chem. Educ. 1995, 72, 88.
Acids / Bases |
Titration / Volumetric Analysis |
Aqueous Solution Chemistry
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Studying Acid-Base Equilibria in Two-Phase Solvent Media: Analyzing Results Using Aqueous Surfactant Solutions with Organic Solvents in the Titration of Analytes with Low Solubilities and Low Dissociation Constants Tucker, Sheryl A.; Amszi, Vicki L.; Acree, William E., Jr.
Authors offer suggestions for the types of problems encountered in an analytical laboratory activity involving the quantitative analysis of weak acids and weak bases.
Tucker, Sheryl A.; Amszi, Vicki L.; Acree, William E., Jr. J. Chem. Educ. 1993, 70, 80.
Acids / Bases |
Quantitative Analysis |
Solutions / Solvents |
Titration / Volumetric Analysis
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Schiff base puzzle project. Todd, David.
Students pick an unknown substituted aniline and a substituted benzaldehyde, produces the corresponding Schiff base from them, and compares its melting point to those of 25 possible Schiff bases (their structures and melting points being given).
Todd, David. J. Chem. Educ. 1992, 69, 584.
Qualitative Analysis |
Aldehydes / Ketones |
Amines / Ammonium Compounds
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Consumer applications of chemical principles: Drugs Hill, John W.; Jones, Susan M.
Acid-base chemistry of drugs (nicotine, cocaine, and aspirin), general anesthesia (nitrous oxide, enflurane, isoflurane, halothane), local anesthetics (procaine, lidocaine, cocaine), and intravenous anesthetics (thiopental, ketamine hydrochloride, phencyclidine).
Hill, John W.; Jones, Susan M. J. Chem. Educ. 1985, 62, 328.
Consumer Chemistry |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Acids / Bases |
Applications of Chemistry
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Quarternary ammonia salts: Some recent applications in organic synthesis Varughese, Pothen
Presents a variety of applications for quarternary ammonia salts, including as reaction media, a reagent for mesylation, catalytic hydrogenation, and micellar and phase-transfer catalysis.
Varughese, Pothen J. Chem. Educ. 1977, 54, 666.
Synthesis |
Amines / Ammonium Compounds |
Micelles |
Catalysis
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Imidazole - Versatile today, prominent tomorrow Matuszak, C. A.; Matuszak, A. J.
Imidazole chemistry has pedagogical utility for all the organic chemistry students pursing careers in the life sciences.
Matuszak, C. A.; Matuszak, A. J. J. Chem. Educ. 1976, 53, 280.
Grignard Reagents |
Aromatic Compounds |
Heterocycles |
Phenols |
Acids / Bases |
Catalysis |
Coordination Compounds |
Hydrogen Bonding
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The Gabriel synthesis of benzylamine: An undergraduate organic experiment Nigh, W. G.
The Gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine; the reaction is important historically for the synthesis of pure primary amines uncontaminated by secondary or tertiary by-products.
Nigh, W. G. J. Chem. Educ. 1975, 52, 670.
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
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A new chemistry program for nursing and allied health students Stanitski, Conrad L.; Sears, Curtis T., Jr.
Outlines and discusses the topics considered in a chemistry program for nursing and allied health students.
Stanitski, Conrad L.; Sears, Curtis T., Jr. J. Chem. Educ. 1975, 52, 226.
Nonmajor Courses |
Applications of Chemistry |
Medicinal Chemistry |
Oxidation / Reduction |
Catalysis |
Acids / Bases |
pH |
Metabolism |
Drugs / Pharmaceuticals
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Early theories of metal-ammines. A brief historical review from Graham to Claus (1837-1856) Kauffman, George B.
This article considers the development of some earlier theories of the constitution of the most familiar coordination compounds: the metal-ammines-which led up to the classic paper of Carl Ernst Claus.
Kauffman, George B. J. Chem. Educ. 1974, 51, 522.
Coordination Compounds |
Amines / Ammonium Compounds |
Metals
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Benzenesulfonyl chloride does react with tertiary amines. The Hinsberg test in proper prospective Gambill, C. R.; Roberts, T. D.; Shechter, H.
Addresses the long standing myths that tertiary amines do not react with nitrous acid or benzylsulfonyl chloride.
Gambill, C. R.; Roberts, T. D.; Shechter, H. J. Chem. Educ. 1972, 49, 287.
Amines / Ammonium Compounds |
Qualitative Analysis
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The Eschweiler-Clark methylation of amines: An organic chemistry experiment Pine, Stanley H.
In this procedure, benzylamine is converted to N,N-dimethylbenzylamine.
Pine, Stanley H. J. Chem. Educ. 1968, 45, 118.
Amines / Ammonium Compounds |
Synthesis
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Letter to the editor Onwood, D. P.
Discusses variations in the usage of the terms "acid" and "base," including Lowry-Bronsted and Lewis systems.
Onwood, D. P. J. Chem. Educ. 1966, 43, 335.
Acids / Bases |
Lewis Acids / Bases |
Nomenclature / Units / Symbols
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Resolution of D,L-alpha-phenylethylamine: An introductory organic chemistry experiment Ault, Addison
This experiment clarifies several of the concepts of optical isomerism and introduces the techniques of recrystallization, extraction, and distillation.
Ault, Addison J. Chem. Educ. 1965, 42, 269.
Amines / Ammonium Compounds |
Enantiomers |
Chirality / Optical Activity
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