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Oluwafemi Ogungbemiro Owen

Assignment of the IR spectrum of 2,4-pentanedione (acetylacetone)

D. Sigdel  Follow

OH str for beta diketones is tabulated from 3200 to 2400 1/cm. The shift is explained by resonance of the hydrogen bonded structure.

Its absorption features is small or unseen as for

  • commonly the ketonic form is highly dominant; i.e. we won't expect to see OH str in the acetaldehyde spectrum, even

  • owing to the above mentioned resonance, the dipole change associated to symmetric OH str is null, and it is minimal for the AS one.

The symmetry of 2,4-pentanedione makes the last point even more important.

Concerning the second part. The fact that the O of the carbonyl of the enoform is H bonded does further shift down the related CO str. Moreover, in addition to resonance with the C=C, note that again there will be resonance with the CO in beta as above, and this further shift the frequency to lower wn.

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