Hydrogen bonding properties and intermediate structure of N-(2-carboxyphenyl)salicylidenimine

Alette G.J. Ligtenbarg, Ronald Hage, Auke Meetsma, Ben L. Feringa

OnderzoeksoutputAcademicpeer review

50 Citaten (Scopus)
613 Downloads (Pure)


The hydrogen bonding properties, the nature of the tautomeric structure and dimerization of N-(2-carboxyphenyl)salicylidenimine 1 has been studied. The crystal and molecular structure of 1 has been determined by single-crystal X-ray diffraction analysis. This compound forms a dimer in the solid state, which is held together by two strong intermolecular O–H · · · O bridges [O(1) · · · O(2a) = 2.455(1) Å]. This dimeric structure is further stabilized by two intramolecular N–H · · · O hydrogen bonds [N(1) · · · O(1) = 2.654(1) and N(1) · · · O(2) = 2.663(1) Å]. In this way, an eight-membered pseudocycle is created. However, in methanol or acetonitrile solution, no dimerization was observed according to 1H-NMR, IR and UV measurements. It was also found that this compound exists as an intermediate form between a phenol-imine and an o-quinoid structure. In addition, a derivative soluble in chloroform, 2-[2-hydroxy-5-(2-butyl)benzylideneamino]benzoic acid 3, was examined for comparison.
Originele taal-2English
Pagina's (van-tot)807 - 812
Aantal pagina's6
TijdschriftJournal of the Chemical Society, Perkin Transactions 2
Nummer van het tijdschrift4
StatusPublished - 1999

Citeer dit