Infrared and Ultraviolet Absorption Spectra of Alpha-Azido Ethers and Amines

Abstract

The ultraviolet absorption spectra of a series of alpha- azido ethers, alpha- azido thioethers, and alpha- azido amines exhibited extinction coefficient maxima in the region 264–300 mμ A shift to the lower wavelength was found to occur in the order S>O>N when these atoms are substituted alpha to an azido- group. Infrared absorption spectra were recorded in the 2 to IS micron region, and assignments made for the asymmetric and symmetric N3 stretching vibrations. The N3 asymmetric vibration occurred in the range 2141–2090 cm−1 for the azides examined. The N3 symmetric vibration was more variable. Tentative assignments were made lor this absorption occurring for alpha- azido ethers and alpha- azido thioethers. However, no assignment was made for this vibration for the alpha-azido amines due to the complicated spectra in this region. The N3 asymmetric vibration for azidomethyl methyl ether, azidomethyl methyl sulfide and N-azidomethyl phthalimide exhibited a doublet while other azides exhibited a single absorption for this mode.