[Hydrogen bond and acid-base interactions in erythromycin solutions].

Abstract

The association and conformational structure of the molecule of erythromycin in solutions of CCl4, C2Cl4 and CHCl3 were studied by the IR spectra in the region of v OH and vC = O. The analysis of the concentration and temperature changes showed that the erythromycin association was accounted for by the hydrogen linkage of OH ... O = C to the ester group. In the monomer molecule of erythromycin, all hydroxyl groups participated in the intramolecular hydrogen linkage. Band 3513 cm-1 belonged to the OH group in the five-membered cycles of OH ... O. Components 3500, 3530 and 3560 cm-1 of the wide band vOH were assigned to the cycles with OH ... N and OH ... O linkages of a larger size. The association was due to a break in a part of the intramolecular hydrogen linkages. Addition of strong acceptors of proton-hexamethanol and trioctylphosphinoxide to the solution resulted in attenuation of these bands and appearance of a strong band vOH of the erythromycin-acceptor complexes. In the presence of monochloroacetic acid in the solution of CHCl3 stoichiometric protonization of erythromycin was observed. The total acid was in the form of anion (vaCO-2 1610 cm-1) up to a ratio of 1:1. The protonization proceeded according to the nitrogen atom since the antibiotic spectrum in the region of vC=O did not change. Propionic acid titrated erythromycin in methanol solution and in mixtures of water and methanol up to a ratio of 1:5 (v/v). However, in the solution of CHCl3 equilibrium between the neutral and ionized molecules of the acid was seen.