With increasing importance of fluorination as the design strategy in drug discovery, it is important to understand its impact on the compound's properties such as lipophilicity (LogP). Effects of the Fluorine atoms in saturated carbo-and heterocyclic systems are especially interesting, considering their complexity and growing popularity of such scaffolds in medicinal chemistry. In a series of model 4-substituted piperidine-derived benzamides, monoflurination at a tertiary Carbon atom either increased or decreased the compounds' lipophilicity depending on the -substituent. The observed LogP value showed reasonable correlation (R 2 = 0.78) with modified Swain -Lupton field inductive effect parameter F of the -substituent, being positive for more electron-withdrawing and negativefor electron-donating or less electron-withdrawing groups. Qualitative analysis of molecular electrostatic potential surface (MEPS) showed that lowered LogP correlated with extended negative MEPS area caused by the Fluorine atom introduction, and vice versa. Changes in electronic distribution at the -substituent itself were also found to be significant. These results suggest that that the fluorination effect on the compound's lipophilicity in the series studied might be related to electronic distribution alterations at the neighboring atoms (mostly Hydrogen) and not by polarization of the Fluorine atom itself.