Through-Space Polar-π Interactions in 2,6-Diarylthiophenols

Jie Jian, Jordi Poater, Roel Hammink, Paul Tinnemans, Christine McKenzie, F Matthias Bickelhaupt*, Jasmin Mecinović*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

Molecular recognition between polar groups and aromatic molecules is fundamentally important to rational drug design. Although it has been well established that many polar functionalities interact with electron-rich aromatic residues through energetically favorable polar-π interactions, there is a limited understanding of the association between thiols and aromatic systems. Herein we report physical-organic chemistry studies on 2,6-diarylthiophenols that possess the central thiophenol ring and two flanking aromatic rings with tunable electronic properties caused by substituents at distant para position. Hammett analysis revealed that pK a values and proton affinities correlate well with Hammett sigma values of substituents. Additional energy decomposition analysis supported the conclusion that both through-space SH-π interactions and S -π interactions contribute to intramolecular stabilization of 2,6-diarylthiophenols.

Original languageEnglish
JournalChemPhysChem
Volume21
Issue number11
Pages (from-to)1092-1100
ISSN1439-4235
DOIs
Publication statusPublished - 3. Jun 2020

Bibliographical note

© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

  • aromatic compounds
  • molecular recognition
  • noncovalent interactions
  • polar-π interactions
  • thiols

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