How to: Identify Product Using NMR http://chem.chem.rochester.edu/~nvd/characterization.

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Characterization Notes
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A Perfect Reaction (see all): You obtain a proton NMR spectrum of a pure compound without
solvent peaks. Each peak can be assigned to a proton of your target compound, and the
integrations are consistent with expectations. Other spectra can be obtained without complications.

A Nightmare Scenario (see all): All of the peaks in your proton NMR spectrum overlap, the
compound is not the one you expected, and you don't know what it is.

Common Rookie Mistakes: Spectroscopy

Step by Step:

1. Remove all the solvent from your compound by rotoevaporating thoroughly.

Tips (see all)

If the compound is not volatile, put it on a high vacuum line for 10-20 minutes.
Some compounds cling to ethyl acetate. To get rid of residual peaks, try dissolving the
compound in a little dichloromethane, and then rotoevaporating. Repeat three times.
2. Acquire a proton NMR spectrum. Analyze the spectrum to confirm your structure
assignment.

Label any solvent peaks or known impurities.

Label the peaks that correspond to starting material, or known byproducts, if present. This
will be a factor only when purification does not effectively separate compounds.
Label peaks corresponding to isomers, if applicable. Write the ratio of isomers on the
spectrum.
Label the protons of your product (Ha, Hb, etc.) Assign each peak in the spectrum to a
proton of your product.
Consider measuring the spectrum of a single fraction from a column, if purification is
inefficient.
If you have an OH or NH proton you'd like to assign, add a drop of D2O to the sample,
shake thoroughly, and take another proton spectrum.

Often, enough information is gained from proton NMR spectroscopy to identify the product.
Sometimes it is appropriate to gather more characterization data, and sometimes not.

Continue with characterization when

Your advisor recommends it.

The compound is new and publication is planned. The spectrum should contain only product
peaks.
You don't know what the compound is.

Do NOT continue with characterization when

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How to: Identify Product Using NMR http://chem.chem.rochester.edu/~nvd/characterization.html

Your advisor does not recommend additional characterization.

Your compound has been reported previously in the literature and your data matches the
data reported.
It is a routine procedure, you know exactly what you have, and the compound is an
intermediate in a longer synthetic sequence.

Beyond 1H NMR:

IR spectroscopy*
Carbon NMR spectroscopy*
Mass spectroscopy*
Optical Rotation*
2D NMR
nOe experiments
Other specialized NMR experiments; DEPT, HMQC, HMBC

* Necessary for publication often useful for structure determination

See also: Rookie Mistakes, 1H NMR How to, Reaction Checklist, Troubleshooting the
Experiment

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