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Real-World Topics: Medicinal ChemistryArrietta Clauss Instructors often look for real-world topics that interest students when designing labs and preparing lectures. The chemistry associated with drugs is a fertile area, and the archives of the Journal can be a resource for interesting drug-related activities to enhance student learning. Clauss, Arrietta. J. Chem. Educ.2008, 85, 1657.
Enrichment / Review Materials |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Applications of Chemistry
Molecular Models of Polymers Used in Sports EquipmentWilliam F. Coleman The Featured Molecules this month are a number of monomers and their associated polymers used in making equipment for a variety of high-impact sports. The molecules provide students with an introduction to an important area of applied chemistry and also enable them to examine complex structures using the models they have seen applied to small molecules. Coleman, William F. J. Chem. Educ.2008, 85, 1456.
Molecular Modeling |
Molecular Properties / Structure |
Applications of Chemistry
Today's Science for Tomorrow's ScientistsCaroline Pharr Today's Science for Tomorrow's Scientists (TSTS) is an interactive Web site containing modular instructional units that introduce current science research through online tutorials. Research groups can use images, movies, and other interactive functions to share their work with others, particularly students at the elementary, middle, and high school levels. Pharr, Caroline. J. Chem. Educ.2008, 85, 1453.
Molecular Models of Reactants and Products from an Asymmetric Synthesis of a Chiral Carboxylic AcidWilliam F. Coleman Our JCE Featured Molecules for this month come from the paper by Thomas E. Smith, David P. Richardson, George A. Truran, Katherine Belecki, and Megumi Onishi (1). The authors describe the use of a chiral auxiliary, 4-benzyl-2-oxazolidinone, in the synthesis of a chiral carboxylic acid. The majority of the molecules used in the experiment, together with several of the pharmaceuticals mentioned in the paper, have been added to our molecule collection. In many instances multiple enantiomeric and diastereomeric forms of the molecules have been included. This experiment could easily be extended to incorporate various aspects of computation for use in an advanced organic or integrated laboratory. Here are some possible exercises using the R and S forms of the 4-benzyl-2-oxazolidinone as the authors point out that both forms are available commercially. Calculation of the optimized structures and energies of the enantiomers at the HF/631-G(d) level using Gaussian03 (2) produces the results shown in Table 1. Evaluation of the vibrational frequencies results in no imaginary frequencies and the 66 real frequencies are identical for the two forms. Examination of the computed IR spectra also shows them to be identical. Additionally, the Raman and NMR spectra can be calculated for the enantiomers and compared to experimental values and spectral patterns. A tool that is becoming increasingly important for assigning absolute configuration is vibrational circular dichroism (VCD). Although the vibrational spectra of an enantiomeric pair are identical, the VCD spectra show opposite signs, as shown in Figure 1. One can imagine a synthesis, using an unknown enantiomer of the chiral auxiliary, followed by calculations of the electronic and vibrational properties of all of the intermediates and the product, and determination of absolute configuration of reactants and products by comparison of experimental and computed VCD spectra. Using a viewer capable of displaying two molecules that can be moved independently, students could more easily visualize the origin of the enantiomeric preference in the reaction between the chelated enolate and allyl iodide.
