Linear solvation energy relationships. 46. An improved equation for correlation and prediction of octanol/water partition coefficients of organic nonelectrolytes (Including strong hydrogen bond donor solutes)

Octanol/water partition coefficients of 245 non-hydrogen bonding, hydrogen bond acceptor, and weak and strong hydrogen bond donor aliphatic and aromatic solutes are well correlated by the linear solvation energy relationship log K_ow = 0.35 + 5.35V_I/100 - 1.04(π* - 0.35δ) - 3.84β_m + 0.10α_m (r = 0.9959, SD = 0.131), where V_I is the intrinsic (van der Waals) molar volume, π*, β_m, and α_m are the solvatochromic parameters that measure solute dipolarity/polarizability, hydrogen bond acceptor basicity, and hydrogen bond donor acidity, and δ is a "polarizability correction" parameter. Parameter estimation rules are set forth that allow the accurate prediction of octanol/water partition coefficients of hundreds, perhaps thousands, of solutes whose solvatochromic parameters have not yet been measured.