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Beilstein J. Org. Chem. 2011, 7, 1732–1738, doi:10.3762/bjoc.7.203
Graphical Abstract
Scheme 1: Reaction of N-methyl-N-nitrosobenzenesulfonamides 1 with nucleophiles.
Figure 1: Absorption spectra at 25 °C of 5 × 10−5 M aqueous sulfuric acid solutions of: (A) 3a, (B) 3b, (C) 3c...
Figure 2: post-CVA absorption spectra at 25 °C of 5 × 10−5 M aqueous sulfuric acid solutions of: (A) 3a, (B) ...
Figure 3: Plot of pKc against X for the protonation equilibrium of (circles) 3a, (squares) 3b, (triangles) 3c...
Scheme 2: Resonance stabilization of O-protonated N-methylbenzenesulfonamides, 3.
Figure 4: Correlation between pKBH+ and (A) σ or (B) σ+ for compounds 3a–d.
Scheme 3: Tautomeric equilibrium between N- and O-protonated forms of N-methylbenzenesulfonamides, 3.