Formation and dissociation of intra-intermolecular hydrogen-bonded solute-solvent complexes: chemical exchange two-dimensional infrared vibrational echo spectroscopy

Journal of the American Chemical Society
Junrong ZhengM D Fayer

Abstract

2-Methoxyphenol (2MP) solutes form weak complexes with toluene solvent molecules. The complexes are unusual in that the 2MP hydroxyl has an intramolecular hydrogen bond and simultaneously forms an intermolecular hydrogen bond with toluene and other aromatic solvents. In the equilibrated solute-solvent solution, there exists approximately the same concentration of 2MP-toluene complex and free 2MP. The very fast formation and dissociation (chemical exchange) of this type of three-centered hydrogen bond complex were observed in real time under thermal equilibrium conditions with two-dimensional (2D) infrared vibrational echo spectroscopy. Chemical exchange is manifested in the 2D spectrum by the growth of off-diagonal peaks. Both the formation and dissociation can be characterized in terms of the dissociation time constant, which was determined to be 3 ps for the 2MP-toluene complex. The intra-intermolecular hydrogen bond formation is influenced by subtle details of the molecular structure. Although 2MP forms a complex with toluene, it is demonstrated that 2-ethoxyphenol (2EP) does not form complexes to any significant extent. Density functional calculations at the B3LYP/6-31+G(d,p) level suggest that steric effects caused by the ...Continue Reading

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Citations

Jun 20, 2008·Proceedings of the National Academy of Sciences of the United States of America·Haruto IshikawaMichael D Fayer
Dec 25, 2008·Proceedings of the National Academy of Sciences of the United States of America·David E MoilanenM D Fayer
Jul 21, 2007·The Journal of Chemical Physics·Jun-Ho Choi, Minhaeng Cho
Feb 9, 2007·The Journal of Chemical Physics·Jun-Ho ChoiMinhaeng Cho
Nov 9, 2010·The Journal of Chemical Physics·Jessica M Anna, Kevin J Kubarych
Jun 22, 2007·Proceedings of the National Academy of Sciences of the United States of America·Kyungwon KwakM D Fayer
Mar 12, 2016·The Journal of Physical Chemistry. B·Chuanqi GeJunrong Zheng
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Mar 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fengqin LongWei Zhuang
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Apr 13, 2007·Physical Chemistry Chemical Physics : PCCP·Ilya J FinkelsteinMichael D Fayer
Feb 24, 2012·Physical Chemistry Chemical Physics : PCCP·Motohiro BannoKeisuke Tominaga
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Mar 28, 2008·Chemical Reviews·Minhaeng Cho

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