| Summary: | The application of DFT computational method (B3LYP/6-311++G(d,p)) to mono- and poly(CF<sub>3</sub>)substituted naphthalene derivatives helps to study changes in the electronic properties of these compounds under the influence of 11 substituents (-Br, -CF<sub>3</sub>, -CH<sub>3</sub>, -CHO, -Cl, -CN, -F, -NH<sub>2</sub>, -NMe<sub>2</sub>, -NO<sub>2</sub>, and -OH) to confront substituent effects in naphthalene with an analogous situation in benzene. This paper shows the dependencies of theoretically calculated SESE (Substituent Effect Stabilization Energy) values on empirically determined, well-defined Hammett-type constants (<i>σ<sub>p</sub></i>, <i>σ<sub>m</sub></i>, <i>R</i>, and <i>F</i>). Described poly(CF<sub>3</sub>)substituted derivatives of naphthalene are, so far, the most sensitive molecular probes for the substituent effects in the aromatic system. The presence of the trifluoromethyl groups of such an expressive nature significantly increases the sensitivity of the SESE to changes caused by another substitution. Further, the more -CF<sub>3</sub> groups are attached to the naphthalene ring, the more sensitive the probe is. Certain groups of probes show additivity of sensitivity: the obtained sensitivity relates to the sum of the sensitivities of the mono(CF<sub>3</sub>)substituted probes.
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