EFFECT OF STRUCTURE ON THE KINETICS AND MECHANISM OF THE ACID-CATALYZED DECOMPOSITION OF N-ALKYL-N-NITROBENZENESULFONAMIDES
The decomposition rate of a series of meta- and para-substituted N-alkyl-N-nitrobenzenesufonamides was determined by a spectrophotometric method in aqueous sulfuric acid.It was shown that the decomposition of the compounds takes place both by denitration and by cleavage of the N-S bond with the formation fo primary aliphatic N-nitrosamines.Electron-withdrawing substituents in the aromatic ring shift the process toward denitration.
Drozdova, O. A.,Astrat'ev, A. A.,Kuznetsov, L. L.,Selivanov, V. F.
p. 671 - 675
(2007/10/02)
HYDROLYSIS OF AROMATIC SULFONIC ACIDS UNDER THERMODYNAMIC CONTROL OF THE REACTION
Linear mathematical models which describe the hydrolysis of alkyl- and halobenzenesulfonyl acids under the conditions for their isomerization in sulfuric acid have been obtained by the method of mathematical experiment planning.The value of the effective rate constants of hydrolysis calculated according to the models for comparative conditions (150 deg C, 3 moles of 85percent sulfuric acid) were used to obtain the correlation between log kh and the ? constants of the substituents.The correlation corresponds the electrophilic nature of the hydrolysis process (ρ = -4.69).The strong influence of the electronic effects of the substituents on the rate of hydrolysis is an indication of the development of a considerable positive charge on the reaction center in the transition state.
Krylov, E. N.,Volgina, L. V.,Isaeva, G. Yu.
p. 1129 - 1133
(2007/10/02)
EFFECT OF STRUCTURE ON THE KINETICS AND MECHANISM OF THE ACID-CATALYZED DECOMPOSITION OF N-NITROBENZENESULFONAMIDES
The decomposition rate of a series of ring-substituted N-nitrobenzenesulfonamides in aqueous sulfuric acid was measure by a spectrophotometric method.Decomposition of the compounds takes place both by the cleavage of the N-S bond to form the corresponding sulfonic acid, nitrous oxide, and water and by denitration.In crease in the electronegativity of the substituent in the aromatic ring promotes the denitration reaction.
Drozdova, O. A.,Astrat'ev, A. A.,Kuznetsov, L. L.,Selivanov, V. F.
p. 2063 - 2067
(2007/10/02)
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