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Published on: December 29, 2016
Neighboring Chalcogen Bonding for Controlling Dynamic Imine Chemistry in Aqueous Media
Yong Zhou1,2,3, Qinman Zhang1,2,3, Shuaipeng Jia2,4
1College of Chemistry, Fuzhou University, Fuzhou 350108, P. R. China.
Abstract:
The impact of varied chalcogen bonds (sulfur, selenium, tellurium, and telluronium) on dynamic imine chemistry in aqueous solution is presented by introducing a carboxylate group or cationic telluronium into arylaldehydes. The role of chalcogen bonding in regulating the kinetics and thermodynamics of imine formation/exchange was elucidated through experimental and computational evidence, affording the largest effect for tellurium/telluronium compounds. By leveraging multivalent chalcogen bonding, telluronium-containing aldehyde enabled labeling of the N-terminus of amino acids in neutral buffer.
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