13.5: IR and UV–Vis Spectroscopy of Carboxylic Acids
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency, 1710 cm−1. The C=O bond of the conjugated aliphatic and aromatic carboxylic acids shows an even lower stretching frequency at 1690 cm−1.
In IR spectra of carboxylic acids, the stretching absorptions for the C–H and O–H bonds overlap and exhibit absorption around 3000 cm−1, having sharp C–H peaks and a broad O–H peak. Many carboxylic acids also exhibit small spikes or shoulder bands between 2500 and 2700 cm−1.
UV–vis spectroscopy of the carboxylic acids shows a weak band at a lower wavelength of 200–215 nm due to an n→π∗ transition. However, in highly conjugated carboxylic acids, the n→π∗ transition shifts to a higher wavelength with higher molar absorptivity.
