Novel unsymmetrically N-substituted N,N'-R1N"-R-2-1,3,5-triazacyclohexanes (1b and 2b; R-1 = p-chlorophenyl or p-methoxyphenyl and R-2 = butyl or cyclohexyl) have been synthesized in a good yield from condensation reaction by excess amine. Both triazacyclohexane rings have chair conformation. However, 1b adopts diaxial orientation of aryl groups and an equatorial form of alkyl group whereas 2b prefers an axial orientation of the alkyl group and diequatorial forms of aryl groups. 1b is consolidated by weak C-H center dot center dot center dot pi interactions. Intra-molecular C-H center dot center dot center dot O or C-H center dot center dot center dot N hydrogen bonds and C-H center dot center dot center dot pi may be effective in the stabilization of 2b. Both compounds have showed moderate antimicrobial activity, but 1b exhibits higher activity than 2b. All experimental results are found in good support to theoretical data. Findings of research may be helpful guide for the medicinal chemists and the field is further open for pharmacokinetics studies. (C) 2017 Elsevier B.V. All rights reserved.