Journal of the American Chemical Society · 2006 · 91 citations · 4 references
Natural SciencesChemistryMedicinal ChemistryComputational ChemistryPhysical ChemistryTheoretical ChemistryAb Initio MethodsChemical BondingIntermolecular InteractionsMolecular BondingMolecular Orbital TheoryPotential Energy SurfacesBondingCharge Transfer InteractionsEnthalpyHydrogen Bond EnergeticsIntermolecular Potential Energy SurfacesMolecular Potential Energy SurfacesNonbonded InteractionsReaction Enthalpy
The N-H...O H-bonding enthalpy between 4-pyridones connected in a chain of H-bonds can achieve 23 kcal/mol for the most central H-bonds, while that between two 4-pyridones is 9.90 kcal/mol based upon DFT calculations on the counterpoise-corrected potential energy surfaces. That the range of enthalpies for N-H...O H-bonds can vary from as little as 2 to as much 23 kcal/mol depends primarily upon the polarizability of whatever internally connects the N-H and C=O within the H-bonding molecule, which are two parallel -C=C- entities in 4-pyridone. The contribution of covalent or charge-transfer interactions between the pi-systems of adjacent 4-pyridones is small.
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P. Gilli, V. Bertolasi, V. Ferretti et al. · Journal of the American Chemical Society · 2000 · 511 citations
V. Bertolasi, P. Gilli, V. Ferretti et al. · Acta Crystallographica Section B Structural Science · 1998 · 54 citations