Difference between Primary Secondary and Tertiary Amines Via FTIR

In FTIR (Fourier Transform Infrared) spectroscopy, primary, secondary, and tertiary amines can be distinguished based on the characteristic infrared absorption bands associated with their functional groups. Here’s a brief overview of the differences in the FTIR spectra of primary, secondary, and tertiary amines:

  1. Primary Amines:
    • Functional Group: In primary amines, the nitrogen atom is bonded to two hydrogen atoms and one carbon atom.
    • FTIR Absorption Bands:
      • N-H Stretching: Primary amines exhibit a strong absorption band in the range of 3300 to 3500 cm⁻¹ due to the stretching vibration of the N-H bond.
      • C-H Stretching: The C-H stretching vibrations of the aliphatic chain can be observed around 2800 to 3000 cm⁻¹.
    • Example: For example, if you have n-butylamine, the primary amine functional group contributes to these characteristic bands in its FTIR spectrum.
  2. Secondary Amines:
    • Functional Group: In secondary amines, the nitrogen atom is bonded to two carbon atoms and one hydrogen atom.
    • FTIR Absorption Bands:
      • N-H Stretching: Secondary amines also exhibit a N-H stretching absorption band, but it is generally weaker compared to primary amines and is often observed around 3200 to 3300 cm⁻¹.
      • C-H Stretching: The C-H stretching vibrations of the aliphatic chain are present around 2800 to 3000 cm⁻¹.
    • Example: If you have dimethylamine, the secondary amine functional group contributes to these characteristic bands in its FTIR spectrum.
  3. Tertiary Amines:
    • Functional Group: In tertiary amines, the nitrogen atom is bonded to three carbon atoms.
    • FTIR Absorption Bands:
      • N-H Stretching: Tertiary amines do not have a significant N-H stretching absorption band, as there are no hydrogen atoms directly bonded to the nitrogen.
      • C-H Stretching: The C-H stretching vibrations of the aliphatic chain are present around 2800 to 3000 cm⁻¹.
    • Example: If you have trimethylamine, the tertiary amine functional group contributes to these characteristic bands in its FTIR spectrum.

The distinguishing feature in FTIR spectra of primary, secondary, and tertiary amines lies in the N-H stretching absorption bands. Primary amines typically have a strong N-H stretching band, secondary amines have a weaker N-H stretching band, and tertiary amines lack a significant N-H stretching band. Additionally, the C-H stretching vibrations of the aliphatic chain are common features in the spectra of all three types of amines. Interpretation of FTIR spectra involves considering the specific functional groups present in the molecule and their characteristic absorption bands.