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Title:Investigating Substituent Effects In Dispersion-controlled Acetophenone-phenol Balances
Author(s):Zimmermann, C.
Contributor(s):Suhm, Martin A.
Subject(s):Non-covalent interactions
Abstract:\begin{wrapfigure}{r}{0pt} \includegraphics[scale=0.6]{PhenylAce_Balance.eps} \end{wrapfigure} The carbonyl oxygen of the asymmetrically substituted ketone acetophenone exhibits two hydrogen bond docking sites, where in combination with a phenol molecule two competing isomers can be formed. The two conformers can be probed experimentally by analyzing the differences in the OH-stretching frequency via FTIR spectroscopy in a supersonic jet and determining their abundance ratio at low temperatures. \footnote{C. Zimmermann et al., \emph{Phys. Chem. Chem. Phys.}, \textbf{2020}, \emph{22}, 2870. } This allows for the experimental benchmarking of theoretically predicted relative conformational energies on a kJ mol$^{-1}$ or even finer scale. \footnote{H. C. Gottschalk et al., \emph{J. Chem. Phys.}, \textbf{2018}, \emph{148}, 014301.}\footnote{A. Poblotzki et al., \emph{J. Phys. Chem. Lett.}, \textbf{2017}, \emph{8}, 5656.} By halogenating the second or fourth position in the phenyl-ring of the acetophenone molecule with fluorine, chlorine or bromine, six closely related systems are formed, allowing to probe the influence of substituent effects on the favored docking site in addition to the London dispersion attraction and steric hindrances.
Issue Date:2021-06-23
Publisher:International Symposium on Molecular Spectroscopy
Genre:Conference Paper / Presentation
Date Available in IDEALS:2021-09-24

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