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1 article(s) from Pessêgo, Márcia

Equilibrium constants and protonation site for N-methylbenzenesulfonamides

José A. Moreira,
Ana M. Rosa da Costa,
Luis García-Río and
Márcia Pessêgo

Beilstein J. Org. Chem. 2011, 7, 1732–1738, doi:10.3762/bjoc.7.203

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Graphical Abstract

Scheme 1: Reaction of N-methyl-N-nitrosobenzenesulfonamides 1 with nucleophiles.

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Figure 1: Absorption spectra at 25 °C of 5 × 10⁻⁵ M aqueous sulfuric acid solutions of: (A) 3a, (B) 3b, (C) 3c...

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Figure 2: post-CVA absorption spectra at 25 °C of 5 × 10⁻⁵ M aqueous sulfuric acid solutions of: (A) 3a, (B) ...

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Figure 3: Plot of pK_c against X for the protonation equilibrium of (circles) 3a, (squares) 3b, (triangles) 3c...

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Scheme 2: Resonance stabilization of O-protonated N-methylbenzenesulfonamides, 3.

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Figure 4: Correlation between pK_BH+ and (A) σ or (B) σ⁺ for compounds 3a–d.

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Scheme 3: Tautomeric equilibrium between N- and O-protonated forms of N-methylbenzenesulfonamides, 3.

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Full Research Paper

Published 27 Dec 2011

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