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The N–H stretches of amines are in the region 3300-3000 cm-1. These bands are weaker and sharper than those of the alcohol O–H stretches which appear in the same region. In primary amines (RNH2), there are two bands in this region, the asymmetrical N–H stretch and the symmetrical N–H stretch.
Secondary amines (R2NH) show only a single weak band in the 3300-3000 cm-1 region, since they have only one N–H bond. Tertiary amines (R3N) do not show any band in this region since they do not have an N–H bond.
(A shoulder band usually appears on the lower wavenumber side in primary and secondary liquid amines arising from the overtone of the N–H bending band: this can confuse interpretation. Note the spectrum of aniline, below.)
The N–H bending vibration of primary amines is observed in the region 1650-1580 cm-1. Usually, secondary amines do not show a band in this region and tertiary amines never show a band in this region. (This band can be very sharp and close enough to the carbonyl region to cause students to interpret it as a carbonyl band.)
Another band attributed to amines is observed in the region 910-665 cm-1. This strong, broad band is due to N–H wag and observed only for primary and secondary amines.
The C–N stretching vibration of aliphatic amines is observed as medium or weak bands in the region 1250-1020 cm-1. In aromatic amines, the band is usually strong and in the region 1335-1250 cm-1.
- N–H stretch 3400-3250 cm-1
- 1° amine: two bands from 3400-3300 and 3330-3250 cm-1
- 2° amine: one band from 3350-3310 cm-1
- 3° amine: no bands in this region
- N–H bend (primary amines only) from 1650-1580 cm-1
- C–N stretch (aromatic amines) from 1335-1250 cm-1
- C–N stretch (aliphatic amines) from 1250–1020 cm-1
- N–H wag (primary and secondary amines only) from 910-665 cm-1
The spectrum of aniline is shown below. This primary amine shows two N–H stretches (3442, 3360); note the shoulder band, which is an overtone of the N–H bending vibration. The C–N stretch appears at 1281 rather than at lower wavenumbers because aniline is an aromatic compound. Also note the N–H bend at 1619.
The spectrum of diethylamine is below. Note that this secondary amine shows only one N–H stretch (3288). The C–N stretch is at 1143, in the range for non-aromatic amines (1250-1020). Diethylamine also shows an N–H wag (733).
Triethylamine is a tertiary amine and does not have an N–H stretch, nor an N–H wag. The C–N stretch is at 1214 cm-1 (non-aromatic).