In this paper, we used bond-length equalization, aromatic stabilization energies (ASE) and nucleusindependent chemical shifts (NICS), calculated with (density functional theory) B3LYP levels at the 6-311 + G * * basis set, to evaluate the aromaticity of a set of 38 five-member planar π -electron aromatic systems: sila-, aza-and phosphaderivatives and their parent systems. The result revealed statistically significant correlations among the above three criteria, and the order of aromaticity of the whole set was: Aza-derivatives rings > Phospha-derivatives rings > Siladerivatives rings > Carbon-containing rings; NICS(0.6) and NICS(0.8) had the same results in evaluating the order of aromaticity in our case.