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Strong Hydrogen Bonding to the Amide Nitrogen Atom in an “Amide Proton Sponge”: Consequences for Structure and Reactivity
Author(s) -
Cox Christopher,
Wack Harald,
Lectka Thomas
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990315)38:6<798::aid-anie798>3.0.co;2-w
Subject(s) - amide , reactivity (psychology) , nitrogen atom , hydrogen bond , nitrogen , proton , chemistry , hydrogen atom , hydrogen , atom (system on chip) , crystallography , stereochemistry , molecule , organic chemistry , group (periodic table) , physics , medicine , alternative medicine , pathology , quantum mechanics , computer science , embedded system
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.