Kinetic and mechanistic studies of reactions of aniline and substituted anilines with chloramine T

V-M Ramanujam, Norman M. Trieff

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Abstract

Rates of reactions of aniline and substituted anilines with chloramine T (CAT) to form N-chloroanilines have been measured. Each reaction showed first-order dependence on CAT and fractional order dependence on the amine. The latter observation indicates that the reaction involves formation of a complex in a fast equilibrium step followed by slow decomposition of the complex. The equilibrium constant (K) for the formation of the complex and its decomposition rate constant (k2) in each case have been calculated from the plot of 1/Kobs versus 1/[amine]. In addition, the reaction constant (p-0.976. obtained from a Hammett plot) and thermodynamic parameters have been evaluated, and mechanisms are proposed.

Original languageEnglish (US)
Pages (from-to)1275-1280
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number10
StatePublished - 1977

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Aniline Compounds
Amines
Rate constants
Decomposition
Kinetics
Equilibrium constants
Thermodynamics
chloramine-T
aniline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Rates of reactions of aniline and substituted anilines with chloramine T (CAT) to form N-chloroanilines have been measured. Each reaction showed first-order dependence on CAT and fractional order dependence on the amine. The latter observation indicates that the reaction involves formation of a complex in a fast equilibrium step followed by slow decomposition of the complex. The equilibrium constant (K) for the formation of the complex and its decomposition rate constant (k2) in each case have been calculated from the plot of 1/Kobs versus 1/[amine]. In addition, the reaction constant (p-0.976. obtained from a Hammett plot) and thermodynamic parameters have been evaluated, and mechanisms are proposed.",
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AU - Trieff, Norman M.

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AB - Rates of reactions of aniline and substituted anilines with chloramine T (CAT) to form N-chloroanilines have been measured. Each reaction showed first-order dependence on CAT and fractional order dependence on the amine. The latter observation indicates that the reaction involves formation of a complex in a fast equilibrium step followed by slow decomposition of the complex. The equilibrium constant (K) for the formation of the complex and its decomposition rate constant (k2) in each case have been calculated from the plot of 1/Kobs versus 1/[amine]. In addition, the reaction constant (p-0.976. obtained from a Hammett plot) and thermodynamic parameters have been evaluated, and mechanisms are proposed.

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