University of Illinois Urbana-Champaign

Sulfur hydrogen bonding in the oligomers of aromatic thiols

Juanes, Marcos

Content Files
1467266.pdf
3998.pdf

Permalink

https://hdl.handle.net/2142/104421

Description

Title
Sulfur hydrogen bonding in the oligomers of aromatic thiols
Author(s)
Juanes, Marcos
Contributor(s)
  • Fernández, José A.
  • Lesarri, Alberto
  • Saragi, Rizalina Tama
Issue Date
2019-06-18
Keyword(s)
Non-covalent interactions
Date of Ingest
  • 2019-07-15T22:16:53Z
  • 2020-01-25T19:31:38Z
Abstract
\begin{wrapfigure}{l}{0pt} \includegraphics[scale=0.3]{Image2.eps} \end{wrapfigure} Following previous experiments on sulfur hydrogen bonding\footnote{M. Juanes, A. Lesarri, R. Pinacho, E. Charro, J. E. Rubio, L. Enríquez, M. Jaraíz, \textit{Chem. Eur. J.}, \textbf{2018}, 24, 6564} we have observed several oligomers of the aromatic thiols thiophenol, phenylmethanethiol and 2-phenylethanethiol in a jet-cooled expansion using broadband (chirped-pulsed) microwave spectroscopy (2-8 GHz).The homodimers of the three aromatic thiols are primarily stabilized by S-H $\cdot$$\cdot$$\cdot$ S hydrogen bonds and other weak interactions. The phenylmethanethiol and 2-phenylethanethiol dimers exhibit additional combinations of S-H $\cdot$$\cdot$$\cdot$ $\pi$, C-H $\cdot$$\cdot$$\cdot$ $\pi$ or C-H $\cdot$$\cdot$$\cdot$ S interactions, while the two phenyl rings in the thiophenol dimer are stacked, displaying a $\pi$-$\pi$ interaction. A single symmetric-top isomer of the thiophenol trimer has been observed, characterized by a C$_{3}$ symmetry topologically equivalent to that observed in the phenol\footnote{N. A. Seifert, A. L. Steber, J. L. Neill, C. Pérez, D. P. Zaleski, B. H. Pate, A. Lesarri, \textit{Phys. Chem. Chem. Phys.}, \textbf{2013}, 15, 11468} and aniline\footnote{C. Pérez, I. León, A. Lesarri, B. H. Pate, R. Martínez, Judith Millán, J. A. Fernández, \textit{Angew. Chem. Int. Ed.}, \textbf{2018}, 57, 15112} trimers. The trimer structure combines S-H $\cdot$$\cdot$$\cdot$ S hydrogen bonds and C-H $\cdot$$\cdot$$\cdot$ $\pi$ interactions. Accurate rotational parameters and supporting ab initio and DFT calculations will be reported at the symposium.
Publisher
International Symposium on Molecular Spectroscopy
Type of Resource
text
Genre of Resource
Conference Paper / Presentation
Language
eng
Permalink
http://hdl.handle.net/2142/104421
DOI
https://doi.org/10.15278/isms.2019.TB03
Copyright and License Information
Copyright 2019 Marcos Juanes

Owning Collections

Abstracts & Presentations - 2019 International Symposium on Molecular Spectroscopy PRIMARY