Synthesis and Infrared Spectroscopic Investigation of Hydrogen-Bonded Complexes between 1,8-Bis(Dimethylamino)Naphthalene and 2,6-Dihydroxynaphthalene in 2:1 and 1:2 Ratios in the Crystalline forms and in Acetonitrile

Abstract

Two hydrogen bonded complexes between 1,8- bis(dimethylamino) naphthalene (DMAN) and 2,6-dihydroxynaphthalene (DHN) in 2:1 and 1:2 ratios were synthesised and studied using FTIR the spectra of the solid 2:1 complex revealed incomplete protonation of DMAN with the appearance of two broad absorptions representing ν(NHN)+ and ν(OHN) in the ranges 700–400 and 1600–700 cm−1 respectively, while the 1:2 complex indicated the complete protonation of DMAN with the appearance of two broad absorptions representing ν(NHN)+ and ν(OHO-) in the ranges 700–400 and 1600–700 cm−1 respectively. On the other hand the IR spectra in acetonitrile indicated that the 1:2 complex is more stable than the 2:1 complex.