University of Ottawa NMR Facility Web Site

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Friday, October 29, 2010

NMR and Food Chemistry - Coffee

Many of us enjoy a hot delicious cup of coffee. Many (not including myself) will even spend a great deal of money and a great deal of their time in a long queue to get it! The coffee snobs will preach about the differences between a freshly brewed cup of java and the lowly cup of instant coffee. Is there really a difference? Spectrum A in the figure below shows the 13C CPMAS NMR spectrum of ground coffee. Among other things, the spectrum consists of resonances from the woody fibers, polysaccharide gums, tannins, alkaloids and aromatic oils. Spectrum B is the spectrum of used coffee grounds which were subsequently dried. The spectrum is due to the woody fibers and other insoluble material. Spectrum C is the difference between spectrum A and B and represents all the "goodness" of a fresh brewed cup of coffee. Among other things, it represents all of the alkaloids, tannins and aromatic oils. Spectrum D is the 13C CPMAS NMR spectrum of instant coffee which is manufactured by freeze drying brewed coffee. The spectrum is very similar to the difference spectrum, C. This indicates either that the difference between a freshly brewed cup of coffee and a cup of instant coffee lies in very low concentration constituents or that the coffee snobs are wasting their money and time in long queues. I think both are true.

Thursday, October 28, 2010

13C NMR of "Perdeuterated" Solvents

When one acquires a 13C NMR spectrum of a sample, the deuterated solvent is observed with resonances characterized by the J coupling pattern of the deuterons attached to the carbon atoms. (CD = 1:1:1 triplet, CD2 = 1:2:3:2:1 quintet, CD3 = 1:3:6:7:6:3:1 septet). Often, however; small peaks are observed near the main solvent resonances. These are due to other isotopomers of the solvent. An example of this is shown in the bottom spectrum of the figure below for the high frequency resonance of "THF-d8". The spectrum consists mainly of the expected 1:2:3:2:1 quintet however, there is a small peak present on the high frequency side of the quintet marked by the arrow. It is due to one of the components of the C1 resonance from THF-1,2,2,3,3,4,4-d7. The supplier of the solvent claims that the isotopic purity is 99.5 atom % D. If the deuteration is uniform, approximately 0.5 % of the molecules will contain a single proton. Half of these molecules will be mono-protonated on the high frequency carbons. If a DEPT spectrum is acquired on the same sample, the non-protonated carbons are suppressed leaving only the mono-protonated carbons. This is shown in the top spectrum of the figure, which shows a 1:1:1 triplet from CHD. The isotope shift between CHD and CD2 is 0.354 ppm. Other examples can be found here and here.