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Redox‐Controlled Hydrogen Bonding: Turning a Superbase into a Strong Hydrogen‐Bond Donor
Author(s) -
Wild Ute,
Neuhäuser Christiane,
Wiesner Sven,
Kaifer Elisabeth,
Wadepohl Hubert,
Himmel HansJörg
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304882
Subject(s) - deprotonation , hydrogen bond , chemistry , superbase , redox , acceptor , photochemistry , hydrogen , low barrier hydrogen bond , guanidine , inorganic chemistry , catalysis , molecule , organic chemistry , ion , physics , condensed matter physics
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.