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

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