Chiral Recognition Thermodynamics of β-Cyclodextrin: The Thermodynamic Origin of Enantioselectivity and the Enthalpy−Entropy Compensation Effect

摘要: The complex stability constant (K), standard free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) for the 1:1 inclusion complexation of 43 enantiomeric pairs chiral guests with β-cyclodextrin at 25 °C have been determined by microcalorimetry. overall thermodynamics are related to variations in structure cyclic acyclic guest, including its aromatic or aliphatic nature, chain length, branching, flexibility, charge, incorporated oxygen atom. differences thermodynamic parameters due chirality comprehensively discussed terms stereochemistry, skeleton, functional groups mode penetration upon complexation. enthalpy−entropy compensation plot, using differential (ΔΔH° ΔTΔS° 298.15 K) recognition equilibrium, gave an excellent straight line unit slope, from which isokinetic, isoenantiodifferentiating, temperature was calculat...