ERIC Number: EJ1090647
Record Type: Journal
Publication Date: 2016-Feb
Abstractor: As Provided
Synthesis and Characterization of Calixarene Tetraethers: An Exercise in Supramolecular Chemistry for the Undergraduate Organic Laboratory
Debbert, Stefan L.; Hoh, Bradley D.; Dulak, David J.
Journal of Chemical Education, v93 n2 p372-375 Feb 2016
In this experiment for an introductory undergraduate organic chemistry lab, students tetraalkylate tertbutylcalixarene, a bowl-shaped macrocyclic oligophenol, and examine the supramolecular chemistry of the tetraether product by proton nuclear magnetic resonance (NMR) spectroscopy. Complexation with a sodium ion reduces the conformational mobility of the macrocycle through host-guest interactions, greatly simplifying the [superscript 1]H NMR spectrum of the macrocycle and providing an excellent example of geminal coupling between the diastereotopic protons of the methylene bridges. By dealing explicitly with the organic chemistry of large molecules and host-guest complementarity, this experiment provides a useful pedagogical bridge from small-molecule organic chemistry to the biochemistry of macromolecules such as enzymes.
Descriptors: Synthesis, Undergraduate Students, Organic Chemistry, Laboratory Experiments, Molecular Structure, Spectroscopy, Laboratory Procedures, Teaching Methods
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: firstname.lastname@example.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Sponsor: National Science Foundation (NSF)
Authoring Institution: N/A
Identifiers - Location: Wisconsin
Grant or Contract Numbers: CHE0923473