The effect of fluorine substitution in alcohol-amine complexes
作者： Anne S Hansen , Lin Du , Henrik G Kjaergaard , None
DOI: 10.1039/C4CP02500H
关键词:
摘要: The effect of fluorine substitution on the hydrogen bond strength in alcohol–amine molecular complexes was investigated, with a combination vapour phase infrared spectroscopy and theoretical calculations. were combined from methanol (MeOH), ethanol (EtOH) trifluoroethanol (TFE) as donor, either dimethylamine (DMA) or trimethylamine (TMA) acceptor. fundamental OH-stretching vibration involved bonding measured for all complexes, well weak second NH-stretching overtone DMA complexes. Equilibrium constants complex formation determined by combining calculated intensity integrated absorbance. observation two transitions alcohol–DMA provides an opportunity independent determinations equilibrium constants. Molecular interactions between monomers elucidated Natural Bond Orbital, Atoms Molecules Non-covalent Interactions analysis. We find that TFE donor form stronger bonds secondary increase MeOH to EtOH TFE. is acid than making OH weaker, frequency redshifted relative EtOH. This redshift small but significantly enhanced upon complexation.
harvard.edu
rsc.org
sci-hub.se 参考文章(56)
Kasper Mackeprang, Henrik G. Kjaergaard, Teemu Salmi, Vesa Hänninen, Lauri Halonen, The effect of large amplitude motions on the transition frequency redshift in hydrogen bonded complexes: A physical picture Journal of Chemical Physics. ,vol. 140, pp. 184309- ,(2014) , 10.1063/1.4873420
Waro Nakanishi, Satoko Hayashi, Kenji Narahara, Atoms-in-Molecules Dual Parameter Analysis of Weak to Strong Interactions: Behaviors of Electronic Energy Densities versus Laplacian of Electron Densities at Bond Critical Points Journal of Physical Chemistry A. ,vol. 112, pp. 13593- 13599 ,(2008) , 10.1021/JP8054763
Simone Aloisio, Joseph S. Francisco, Radical−Water Complexes in Earth's Atmosphere Accounts of Chemical Research. ,vol. 33, pp. 825- 830 ,(2000) , 10.1021/AR000097U
L. H. Mukherjee, Ernest Grunwald, PHYSICAL PROPERTIES AND HYDROGEN-BONDING IN THE SYSTEM ETHANOL-2,2,2-TRIFLUOROETHANOL The Journal of Physical Chemistry. ,vol. 62, pp. 1311- 1314 ,(1958) , 10.1021/J150568A034
W. Klemperer, V. Vaida, Molecular complexes in close and far away Proceedings of the National Academy of Sciences of the United States of America. ,vol. 103, pp. 10584- 10588 ,(2006) , 10.1073/PNAS.0508231103
Tobias N. Wassermann, Martin A. Suhm, Ethanol Monomers and Dimers Revisited: A Raman Study of Conformational Preferences and Argon Nanocoating Effects Journal of Physical Chemistry A. ,vol. 114, pp. 8223- 8233 ,(2010) , 10.1021/JP104861Q
V. Vaida, J. S. Daniel, H. G. Kjaergaard, L. M. Goss, A. F. Tuck, Atmospheric absorption of near infrared and visible solar radiation by the hydrogen bonded water dimer Quarterly Journal of the Royal Meteorological Society. ,vol. 127, pp. 1627- 1643 ,(2001) , 10.1002/QJ.49712757509
Henrik G. Kjaergaard, Anna L. Garden, Galina M. Chaban, R. Benny Gerber, Devin A. Matthews, John F. Stanton, Calculation of vibrational transition frequencies and intensities in water dimer: comparison of different vibrational approaches. Journal of Physical Chemistry A. ,vol. 112, pp. 4324- 4335 ,(2008) , 10.1021/JP710066F
D. J. Millen, J. Zabicky, 565. Hydrogen bonding in gaseous mixtures. Part V. Infrared spectra of amine–alcohol systems J. Chem. Soc.. ,vol. 0, pp. 3080- 3085 ,(1965) , 10.1039/JR9650003080
Jonas Elm, Merete Bilde, Kurt V. Mikkelsen, Assessment of Density Functional Theory in Predicting Structures and Free Energies of Reaction of Atmospheric Prenucleation Clusters Journal of Chemical Theory and Computation. ,vol. 8, pp. 2071- 2077 ,(2012) , 10.1021/CT300192P