Prev. Article Next Article Table of Contents

Article

Nuclear Overhauser Effect Spectroscopy. An Advanced Undergraduate Experiment

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Michael T. Huggins and Freida Billimoria

Department of Chemistry, University of West Florida, Pensacola, FL 32514

J. Chem. Educ., 2007, 84 (3), p 471

DOI: 10.1021/ed084p471

Publication Date (Web): March 1, 2007

Section:

History, Education, and Documentation

Abstract

The stereochemical features of molecules can have far reaching effects in many areas of science including medicinal chemistry, materials chemistry, and supramolecular chemistry. There have been many techniques developed over the years to determine the absolute configuration of alkenes: the R,S configuration of chiral centers and the most stable conformation of molecules. Yet, very few of these techniques are normally taught in an undergraduate chemistry course. Nuclear Overhauser effect (NOE) spectroscopy has become an essential tool in stereochemical analysis, and with the evolution of the NMR spectrometer, it has become increasingly easier to acquire NOE data. As such, an advanced laboratory experiment has been designed that allows students to use NOESY spectroscopy to conduct conformational analysis studies. In this experiment, students prepare a set of compounds used to study both the configuration of a newly formed double bond (E or Z) and the conformation of the molecule. Using a simple procedure, a wide array of target molecules are prepared, usually in excellent yields. In addition to the configuration of the double bond, the target molecules possess only a single degree of rotational freedom thus simplifying the conformational analysis. Thus, each of the target molecules has four significant spatial arrangements: two configurational isomers with two major conformations of each configuration.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Alkenes

View: Hi-Res PDF | PDF w/ Links

Citing Articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Integrating Computational Molecular Modeling into the Undergraduate Organic Chemistry Curriculum
Allen D. Clauss and Stephen F. Nelsen
Journal of Chemical Education2009 86 (8), 955
- Integrating Computational Molecular Modeling into the Undergraduate Organic Chemistry Curriculum
  Allen D. Clauss and Stephen F. Nelsen
  Journal of Chemical Education2009 86 (8), 955
  An instructional unit is described for integrating computational molecular modeling into the undergraduate organic chemistry laboratory curriculum. The approach emphasizes use of computational modeling as a readily available, efficient tool for ...
  Abstract | Hi-Res PDF | PDF w/ Links
JCE Concept Connections: Computational Molecular Modeling
Xavier Prat-Resina and Bernadette Caldwell
Journal of Chemical Education2009 86 (8), 958
- JCE Concept Connections: Computational Molecular Modeling
  Xavier Prat-Resina and Bernadette Caldwell
  Journal of Chemical Education2009 86 (8), 958
  The Journal has published many resources on computational molecular modeling and using this approach with organic chemistry.
  Abstract | Hi-Res PDF | PDF w/ Links