TIGER

Journal Articles: 16 results
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the 1H and 13C NMR Spectra of N,O-Acetals  Shahrokh Saba, James A. Ciaccio, Jennifer Espinal, and Courtney E. Aman
Describe an undergraduate organic laboratory experiment in which students prepare two N,O-acetals that differ only in a single ring substituent that introduces asymmetry, giving each compound a distinct 1H and 13C NMR spectral pattern that must be explained by students.
Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. J. Chem. Educ. 2007, 84, 1011.
Amines / Ammonium Compounds |
Chirality / Optical Activity |
Green Chemistry |
Heterocycles |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Using "Basic Principles" To Understand Complex Science: Nicotine Smoke Chemistry and Literature Analogies  Jeffrey I. Seeman
The HendersonHasselbalch 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
Isolation of Shikimic Acid from Star Aniseed  Richard Payne and Michael Edmonds
The isolation of shikimic acid from star aniseed is described. This experiment uses Soxhlet extraction followed by ion exchange chromatography to isolate crude shikimic acid from the star aniseed. Subsequent charcoal decolorization and recrystallization from toluene and methanol afford the pure shikimic acid in 27% w/w yield.
Payne, Richard; Edmonds, Michael. J. Chem. Educ. 2005, 82, 599.
Bioorganic Chemistry |
Natural Products |
NMR Spectroscopy |
Plant Chemistry
Investigation of Secondary Metabolites in Plants. A General Protocol for Undergraduate Research in Natural Products  Jonathan Cannon, Du Li, Steven G. Wood, Noel L. Owen, Alexandra Gromova, and Vladislav Lutsky
Typical experimental procedures to extract and isolate individual chemical constituents from a plant, suggestions for some simple procedures to test for selected bioactivity, and explain how the molecular structures of natural products may be determined using spectroscopic techniques.
Cannon, Jonathan; Li, Du; Wood, Steven G.; Owen, Noel L.; Gromova, Alexandra; Lutsky, Vladislav. J. Chem. Educ. 2001, 78, 1234.
Chromatography |
Natural Products |
NMR Spectroscopy |
Separation Science |
Plant Chemistry |
Molecular Properties / Structure |
Drugs / Pharmaceuticals |
Separation Science
Two Faces of Alkaloids  Jirí Dostál
The article discusses and compares the salts and free bases of six well-known alkaloids: nicotine, morphine, cocaine, sanguinarine, allocryptopine, and magnoflorine. Relevance for the biological and medical uses of these compounds is emphasized.
Dostál, Jirí. J. Chem. Educ. 2000, 77, 993.
Acids / Bases |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
Natural Products |
Aromatic Compounds |
Medicinal Chemistry
Discovery of Highly Sweet Compounds from Natural Sources  A. Douglas Kinghorn and Edward J. Kennelly
Discovery of highly sweet compounds from natural sources (particularly plants); assays for sweetness; and specific examples of recently discovered, naturally-occurrring, sweet compounds.
Kinghorn, A. Douglas; Kennelly, Edward J. J. Chem. Educ. 1995, 72, 676.
Natural Products |
Plant Chemistry |
Food Science |
Consumer Chemistry |
Industrial Chemistry |
Enrichment / Review Materials
Isolation of piperine from black pepper  Epstein, William W.; Netz, David F.; Seidel, Jimmy L.
A new and interesting natural product for isolation in the organic chemistry lab. This procedure also introduces students to many important instruments and procedures in organic chemistry.
Epstein, William W.; Netz, David F.; Seidel, Jimmy L. J. Chem. Educ. 1993, 70, 598.
Natural Products |
Chromatography |
Separation Science
Chemistry and popular culture: The 007 bond.  Last, Arthur M.
The purpose of this paper is to show how chemistry references from Bond books and movies can be related to a variety of topics taught in a typical undergraduate chemistry course.
Last, Arthur M. J. Chem. Educ. 1992, 69, 206.
Natural Products |
Industrial Chemistry
The chemistry of coatings   Griffith, James R.
Nature and humankind both produce spectacular coatings. These discussions of coating can contribute valuable chemistry lessons to the introductory curriculum.
Griffith, James R. J. Chem. Educ. 1981, 58, 956.
Applications of Chemistry |
Natural Products |
Materials Science
Natural products. An independent study project  Griffin, Rodger W., Jr.
This paper provides leading references and describes in detail an independent project suitable for students with at least one year of general chemistry.
Griffin, Rodger W., Jr. J. Chem. Educ. 1974, 51, 601.
Natural Products |
Undergraduate Research
Coffee, Tea, or Cocoa. A trio of experiments including the isolation of theobromine from cocoa  Pavia, Donald L.
Isolating caffeine from tea and coffee and theobromine from cocoa.
Pavia, Donald L. J. Chem. Educ. 1973, 50, 791.
Separation Science |
Consumer Chemistry |
Natural Products |
Plant Chemistry
Natural products: A laboratory guide (Ikan, Raphael)  Bobbitt, James M.

Bobbitt, James M. J. Chem. Educ. 1970, 47, A446.
Natural Products
Natural product chemistry: Laboratory research approach for elementary organic courses  O'Connor, Rod
Describes a program designed to introduce macro, semi-micro, and micro techniques of organic chemistry of the types commonly employed in research in natural product chemistry or in biologically-related fields.
O'Connor, Rod J. Chem. Educ. 1965, 42, 492.
Natural Products |
Undergraduate Research |
Separation Science |
Chromatography |
Thin Layer Chromatography |
Synthesis
The reaction of tertiary amines with nitrous acid  Hein, George E.
Examines the history of investigation into the reaction of tertiary amines with nitrous acid as an example of the inherently conservative nature of science and resistance to new concepts.
Hein, George E. J. Chem. Educ. 1963, 40, 181.
Amines / Ammonium Compounds |
Reactions |
Mechanisms of Reactions
Structural variety of natural products  Roderick, William R.
Classes of natural products examined includes alkynes; quinones; benzpyrones; small and large rings; sulfur, nitrogen, and halogen-containing compounds; and new amino acids.
Roderick, William R. J. Chem. Educ. 1962, 39, 2.
Natural Products |
Amino Acids |
Alkynes |
Aromatic Compounds