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Die Aciditätskonstanten von Benzolsulfonamiden und ihre Beeinflussbarkeit durch Substitution
Author(s) -
Willi A. V.
Publication year - 1956
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19560390106
Subject(s) - chemistry , substituent , inductive effect , ionic bonding , series (stratigraphy) , medicinal chemistry , substitution (logic) , atom (system on chip) , computational chemistry , stereochemistry , organic chemistry , ion , paleontology , computer science , embedded system , biology , programming language
Acidity constants at 20° and the ionic strength μ = 0,1 were determined for substituted benzenesulfonamides and two series of substituted benzenesulfonanilides.pK values are plotted versus Hammett's σ constants and ϱ values are calculated. ϱ = 1,06 is obtained for benzenesulfonamides, ϱ = 1,16 for benzenesulfonanilides substituted on the S side, and ϱ = 1,74 for benzenesulfonanilides substituted on the N side. In the latter series, σ values must be applied for p‐NO 2 and p‐CH 3 CO. ϱ values found in this work are compared with those for other reactions, and they are discussed in terms of electrostatic field effects, inductive and mesomeric effects. It is concluded that direct field effects and electronic effects transmitted through the atom chain equally contribute to the free energy change caused by a substituent.