Abstract: The structural parameters of 36 lubricating additives of N-containing heterocyclic derivatives with the matrices of benzoxazole, benzimidazole, benzothiazole, thiazoline and piperazine were calculated by Hartree-Fock ab initio quantum chemistry method. Quantitative Structure-Tribo-ability Relationship(QSTR)of these additives were studied by multiple linear regression (MLR) method. The antiwear properties of additives showed an appropriate relation with the dipole and the total energy, and strongly depended on the matrices. The QSTR models had an acceptable predictive ability, and can be used to design and synthesize new lubricating additives.