Hydrogen bonding and proton transfer between nitro-phenols and lecithin in apolar solvents |
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Authors: | A. Sidorowicz U. Tlatlik-Nowak R. Randomski |
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Affiliation: | 1. Institute of Biochemistry and Biophysics, Academy of Medicine, Wrotaw, Chatubińskiego 10, PL 50-368 Poland;2. Instiute of Organic and Physical Chemistry, Technical University of Wroc?aw, Wroc?aw, Wyspiańskiego 27, Pl 50-370 Poland |
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Abstract: | The interaction of p-nitrophenol (p-NP), 2,4-dinitrophenol (DNP) (II) and 2,4,6-trinitrophenol (TNP)(III) with dipalmitoyllecithin in apolar solvents has been examined by IR and UV spectroscopy. Addition of any nitrophenol to the solution of lecithin in CCl4 causes disappearance of broad absorption band of water bound with lecithin phosphate grops (3150–3600 cm?1), which was accompanied by an insignificant increase of absorption near 3040 and 2800 cm?1. Association of phenolic groups of (I) with the lecithin was observed by disappearance of the free OH absorption band. In UV spectra of (I), complex formation with lecithin results in a 30 nm red shift of phenol long-wave absorption band and in the appearance of an isosbestic point at 303 nm. In the case of III, addition of the lecithin causes a red shift and strong hyperchromic effect, which is accompanied by the appearance of a new absorption band near 420 nm. It was concluded, that nitrophenols displace a part of water from the polar groups of lipids and form hydrogen bonded complexes or ion-pair structures, depending upon acidic properties of the proton donor. |
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Keywords: | hydrogen bonding proton transfer lecithin lipid bilayers |
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