The Fourier transform infrared (FTIR) and FT-Raman spectra of 2-chloro-4-methylaniline and 2-chloro-6-methylaniline have been measured in the range 4000-400 and 4000-100cm(-1), respectively. Utilising the observed FTIR and FT-Raman data, a complete vibrational assignment and analysis of the fundamental modes of the compounds were carried out. The vibrational frequency which were determined experimentally are compared with those obtained theoretically from ab initio HF and DFT gradient calculations employing the HF/6-31G(d,p) and B3LYP/6-31G(d,p) methods for optimised geometries. The geometries and normal modes of vibration obtained from the HF and DFT methods are in good agreement with the experimental data. The normal co-ordinate analysis was also carried out on the basis of ab initio force fields utilising Wilson's FG matrix method. The manifestations of NH-pi interactions and the influence of bulky chlorine and methyl group on the vibrational modes of the amino group are investigated.