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Redox-controlled hydrogen bonding: turning a superbase into a strong hydrogen-bond donor

Abstract Herein the synthesis, structures and properties of hydrogen-bonded aggregates involving redox-active guanidine superbases are reported. Reversible hydrogen bonding is switched on by oxidation of the hydrogen-donor unit, and leads to formation of aggregates in which the hydrogen-bond donor u...

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Bibliographic Details
Main Authors: Wild, Ute (Author) , Neuhäuser, Christiane (Author) , Wiesner, Sven (Author) , Kaifer, Elisabeth (Author) , Wadepohl, Hubert (Author) , Himmel, Hans-Jörg (Author)
Format: Article (Journal)
Language:English
Published: April 22, 2014
In: Chemistry - a European journal
Year: 2014, Volume: 20, Issue: 20, Pages: 5914-5925
ISSN:1521-3765
DOI:10.1002/chem.201304882
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201304882
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201304882
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Author Notes:Ute Wild, Christiane Neuhäuser, Sven Wiesner, Elisabeth Kaifer, Hubert Wadepohl, and Hans-Jörg Himmel
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Summary:Abstract Herein the synthesis, structures and properties of hydrogen-bonded aggregates involving redox-active guanidine superbases are reported. Reversible hydrogen bonding is switched on by oxidation of the hydrogen-donor unit, and leads to formation of aggregates in which the hydrogen-bond donor unit is sandwiched by two hydrogen-bond acceptor units. Further oxidation (of the acceptor units) leads again to deaggregation. Aggregate formation is associated with a distinct color change, and the electronic situation could be described as a frozen stage on the way to hydrogen transfer. A further increase in the basicity of the hydrogen-bond acceptor leads to deprotonation reactions.
Item Description:Gesehen am 20.08.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201304882

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