28188-48-9Relevant academic research and scientific papers
Reactivity of sterically hindered aromatic sulfonic acid derivatives: VII.* hydrolysis of arenesulfonyl chlorides in aqueous acetonitrile
Rubleva,Krut'ko,Mitchenko
, p. 1006 - 1009 (2007/10/03)
Hydrolysis of sterically hindered arenesulfonyl chlorides in aqueous acetonitrile is accelerated by both electron-acceptor and some electron-donor substituents in the benzene ring. A multifactor kinetic model of the process is proposed. 1998 MAHK Hayka/Interperiodica Publishing.
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.
Acid-catalyzed hydrolysis of benzenesulfonamides. Rate enhancements by ortho-alkyl substituents
Wagenaar, Anno,Kirby, Anthony J.,Engberts, Jan B. F. N.
, p. 203 - 205 (2007/10/02)
Pseudo-first-order rate constants have been measured for the acid-catalyzed hydrolysis of a series of N,N-dimethyl- and N-methyl-N-phenylbenzenesulfonamides in 70 percent (v/v) CF3CO2H/H2O at 99 deg C.Analysis of the effect of the alkyl substituents in the benzene ring shows a remarkable rate enhancement by ortho-alkyl groups, in the contrast with a rate retardation of similar substituents in the corresponding benzamides.The rate enhancement in the sulfonamides is attributed to relief of initalstate strain in the transition state for hydrolysis.When the sulfonamide moiety is contained in a five-membered ring fused to a phenyl ring, the rate of hydrolysis is markedly reduced by an ortho-methyl substituent.
