Sulfur hydrogen bonding in the oligomers of aromatic thiols

Juanes, Marcos

Permalink

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

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

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

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

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