Title: Classical and Reverse Substituent Effects in Substituted Anthrol Derivatives
Abstract: Abstract The substituent effect in 1‐, 2‐, and 9‐anthrols is studied by means of B3LYP/6‐311++G(d,p) computation, taking into account substituents (X): NO 2 , CN, OH and NH 2 located in all positions except the adjacent ones. The substituent effect is characterized by approaches based on quantum chemistry: The charge of the substituent active region (cSAR), substituent effect stabilization energy (SESE) and the charge flow index (CFI) describing flow of the charge from X to the fixed group (or vice versa) as well as substituent constants σ . Changes in properties observed in the fixed group (OH) are described by cSAR(OH). Mutual interdependences are found between these descriptors. The HOMA index is used to describe an effect of a substituent on aromaticity of an anthrol hydrocarbon skeleton and of individual rings. In all cases, the classical (influence of X on the properties of OH) and reverse (influence of OH on the properties of X) substituent effects are studied. The latter is clearly documented by the cSAR approach.