63877-64-5Relevant articles and documents
REACTIVITY OF STERICALLY HINDERED DERIVATIVES OF AROMATIC SULFONIC ACIDS II. EFFECTS OF SUBSTRATE STRUCTURE AND MEDIUM POLARITY ON THE HYDROLYSIS OF BENZENESULFONYL CHLORIDES
Vizgert, R. V.,Rubleva, L. I.,Maksimenko, N. N.
, p. 2259 - 2262 (2007/10/02)
The kinetics of the hydrolysis of substituted benzenesulfonyl chlorides XArSO2ClN2 mechanism.
REACTIVITY OF STERICALLY HINDERED DERIVATIVES OF AROMATIC SULFONIC ACIDS. I. EFFECT OF SUBSTITUENTS ON RATE AND MECHANISM OF HYDROLYSIS OF SOME SUBSTITUTED BENZENESULFONYL CHLORIDES
Vizgert, R. V.,Rubleva, L. I.,Maksimenko, N. N.
, p. 727 - 730 (2007/10/02)
The kinetics of the hydrolysis of substituted benzenesulfonyl chlorides XArSO2Cl in 70percent aqueous dioxane at 303, 313, and 323 K were studied by acid-base titration.The effect of the investigated set of substituents cannot be described by a single linear relationship of the Hammett type.The substrates containing methyl groups at the ortho positions of the aromatic ring exhibit enhanced reactivity.The effect of the structural changes in the sulfonyl chlorides on the nature of bond formation and cleavage in the transition state is discussed in terms of the SN2 mechanism.An attempt is made to explain the V-shaped form of the relationship between log k and ? from the standpoint of the hyperconjugation effect, the contribution from which amounts to about 10percent of the ρ value.
