Intra- versus intermolecular hydrogen bonding equilibrium in 2-hydroxy-N,N-diethylbenzamide

Complex studies of the intramolecular versus intermolecular hydrogen bond equilibrium and internal rotation of the N,N-diethylamine group in 2-hydroxy-N,N-diethylbenzamide were conducted. The intramolecular versus intermolecular process in 2-hydroxy-N,N-diethylbenzamide was studied by UV-Vis, NMR, IR and Vapour Pressure Osmometric (VPO) methods as a function of temperature and concentration in non-polar, basic and protic solvents. The unequal positions of the ethyl groups were analysed and the energy barrier to the re-orientation was defined by the NMR method. This paper presents a study into a complicated nature of competitive interaction 2-hydroxy-N,N-diethylbenzamide with the environment by means of the aforesaid methods. Copyright (c) 2008 John Wiley & Sons, Ltd.