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

P. Majewska, J. Paja̧k, M. Rospenk, A. Filarowski

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)130-137
Number of pages8
JournalJournal of Physical Organic Chemistry
Issue number2
Publication statusPublished - Feb 2009
Externally publishedYes


  • Amides
  • Dynamic nmr
  • H bonds
  • Matrix-isolation
  • Self-association

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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