Characterization of 1-azidoadamantane and related 1,2,3-triazoles by 1- and 2-D NMR

CHED 537

John T. Yeoman, yeomanjo@grinnell.edu, T. Andrew Mobley, mobleyt@grinnell.edu, and James G. Lindberg, lindberg@grinnell.edu. Department of Chemistry, Grinnell College, 1116 8th Avenue, Grinnell, IA 50112
As part of a larger project the 1H and 13C signals of the adamantane residue in 1-azidoadamantane (1) and two other 1-adamantyl-1,2,3-triazoles (2) were assigned using 1D 1H and 13C spectra and 2D 1H - 1H COSY, 1H - 13C HMQC and NOESY spectra.

The four 1H signals Ha - Hd were found between 1.5 and 2.5 ppm with two of the signals appearing as a barely resolved pair of doublets. Three of the four 13C signals were found between 25 and 45 ppm. The ambiguities of the 1H and 13C spectra and the contributions of COSY, HMQC and NOESY spectra to the assignments will be presented.

This collection of spectra could be used in an undergraduate classroom to illustrate the utility of common 2D NMR techniques to assignment of signals in a nontrivial problem.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Chemical Education

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007