Elucidating the Binding Mode of Sulfur- and Selenium-Based Cationic Chalcogen-Bond Donors.
Sercan AkbabaTim SteinkeLukas VogelElric EngelageMáté ErdélyiStefan Matthias HuberPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2024)
For a comparison of the interaction modes of various chalcogen-bond donors, 2-chalcogeno-imidazolium salts have been designed, synthesized, and studied by single crystal X-ray diffraction, solution NMR and DFT as well as for their ability to act as activators in an S N 1-type substitution reaction. Their interaction modes in solution were elucidated based on NMR diffusion and chemical shift perturbation experiments, which were supported by DFT-calculations. Our finding is that going from lighter to the heavier chalcogens, hydrogen bonding plays a less, while chalcogen bonding an increasingly important role for the coordination of anions. Anion-π interactions also show importance, especially for the sulfur and selenium derivatives.
Keyphrases
- ionic liquid
- solid state
- density functional theory
- high resolution
- magnetic resonance
- molecular dynamics
- crystal structure
- molecular docking
- molecular dynamics simulations
- electron microscopy
- electron transfer
- magnetic resonance imaging
- transition metal
- dual energy
- transcription factor
- mass spectrometry
- binding protein