Organic spectroscopic analysis by R.J. Anderson, D. Bendell, P W. Groundwater, Edward W. Abel

By R.J. Anderson, D. Bendell, P W. Groundwater, Edward W. Abel

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15b). 16a) and, as expected for intramolecular hydrogen bonding, is independent of concentration (1 64 1 cm- '). 15b has shifted the broad 0-H absorption to lower wavenumber (from 3330 to 3320 cm-'), but the absorption corresponding to nonhydrogen-bonded 0-H at 3584 cm-' is unaffected. 3. As can be observed, the smaller the ring becomes, the more strained the ring (as the bond angles become increasingly removed Infrared Spectroscopy 41 from the idealized angle of 120" for an sp2 hybridized carbon atom and the amount of eclipsing interactions with neighbouring groups increases), and the higher the stretching frequency of the carbonyl group in both the lactones and lactams.

This results in a lower bond order for this bond, and a consequently lower stretching frequency. One interesting aspect of the effect of hydrogen bonding on the IR spectrum of carbonyl compounds is the effect of intra- and intermolecular hydrogen bonding. Intramolecultr hydrogen bonding (within one molecule) is independent of’ the concentration of the sample and so the position of the carbonyl band will not vary with concentration. Intermolecular hydrogen bonding, on the other hand, is dependent upon the concentration, since the more concentrated the sample, the greater the extent of the hydrogen bonding, and so the position of the carbonyl band will vary with concentration.

This addition of spectra results in an increase in the signalto-noise ratio and spectra can be obtained on smaller amounts of material. The method used for sample preparation depends upon the nature of the sample. Liquids are easily examined as films formed when one drop of the liquid is squeezed between two flat sodium chloride plates, which arc transparent to TR radiation in the 4000-666 cm-' region. Solids can be examined as solutions, mulls in Nujol, or as potassium bromide discs. For solutions, a 5% solution of the solid is introduced into a sodium chloride cell, which is usually 1 mm thick.

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