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Strong Hydrogen Bonding to the Amide Nitrogen Atom in an "Amide Proton Sponge": Consequences for Structure and
Christopher Cox1, Harald Wack1, Thomas Lectka1
1Department of Chemistry, Johns Hopkins University, Baltimore, Maryland 21218 (USA), Fax: (+1) 410-516-8420.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Abstract:
N-Protonated amides have been proposed as intermediates in several biologically important reactions, but they have yet to be identified spectroscopically. The first step toward this goal is now reported in the form of spectroscopic and crystallographic proof of a strong intramolecular hydrogen bond between a charged proton donor and an amide nitrogen atom in the "proton sponge" derivative 1; novel reactivity results from this interaction. TfO-= trifluoromethanesulfonate.