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Structure of 1:1 and 1:2 complexes formed by aromatic NH and OH proton donors with aliphatic amines. Possibility of homoconjugated NHN cation formation
Authors:J P Castaneda  G S Denisov  V M Schreiber  
Institution:

Institute of Physics, St. Petersburg University, Peterhof, 198904 St. Petersburg, Russian Federation

Abstract:Structure of the complexes with NHcdots, three dots, centeredN hydrogen bond formed by bis(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-amine ((4-CF3C6F4)2NH, FA) as proton donor with aliphatic amines (dibutyl-, tributyl- and trimethylamines) as proton acceptors in aprotic solvents (isooctane and methylene chloride) in a wide range of concentrations and temperatures have been studied by IR and UV spectra. Quantitative treatment of the spectra by a computer program based on factor analysis reveals the equilibrium between free molecules and FA–aliphatic amine complexes of 1:1 and 1:2 composition, the latter having an ionic structure with proton transferred from FA to the aliphatic amine. Thermodynamic characteristics of the 1:1 and 1:2 complexes for FA+dibutylamine system have been measured. Appearance of IR bands indicating formation of NHN+ homoconjugated cation has been detected in FA+trimethylamine solution in methylene chloride at temperatures 190–150 K. Spectral manifestations of the complexes containing the (trimethylamine-H-trimethylamine)+ cation, formed by FA and OH proton donor (pentachlorophenol) are compared.
Keywords:Hydrogen bond  Proton transfer  Homoconjugated cation  Bis(2  3  5  6-tetrafluoro-4-trifluoromethyl-phenyl)-amine  UV spectra  IR spectra
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