The transient formation of nitrilimine in aqueous conditions is greatly influenced by pH and chloride. In basic conditions (pH 10) with no chloride, a diarylnitrilimine precursor readily ionizes to form diarylnitrilimine that reacts almost instantly with an acrylamide-containing protein and fluorescently labels it.
X. S. Wang, Y. Lee and W. R. Liu, Chem. Commun., 2014, 50, 3176 DOI: 10.1039/C3CC48682F
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