2(1H)-pyridinone (2-pyridone): self-association and association with water - Spectral and structural characteristics: infrared study and ab initio calculations

摘要

DFT calculations of 2(1H)-pyridinone (2-pyridone NHP), the centrosymmetric dimer (NHP)2 and the closed complexes (NHP, H2O) and (NHP, 2H(2)O), with their deuterated homologues NDP, (NDP)(2), (NDP, D2O) and (NDP, 2D(2)O), are compared with vibrational spectra of NHP and NDP in ternary mixtures CH3CN, NHP, H2O. Experimental data are also obtained for NHP or NDP in various solvents. The protic solvent effects demonstrate that mechanical couplings are different in the 1500-1700 cm(-1) range for the v(C=O) and v(8b) (valence of the ring) modes in NHP and NDP (or (NHP, H2O) and (NDP, D2O)). For the first time, data are obtained for NDP in the dimer (NHP, NDP). Comparison of data for pyridone, monomer, dimer or complexed with water, shows that in the complexes, water is a weaker proton acceptor and a stronger proton donor than a second pyridone molecule in the centrosymmetric dimer. (C) 2003 Elsevier B.V. All rights reserved. [References: 39]