Micellar effects on the rates of formation and decomposition of the hydroxy Meisenheimer complex of 1,3,6,8-tetranitronaphthalene
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 1377-1380
- https://doi.org/10.1039/j29710001377
Abstract
The surface-active cation hexadecyltrimethylammonium bromide (CTAB) increases, the anion sodium dodecyl sulphate (NaLS) decreases, and the uncharged polyoxyethylene (15) nonylphenol (lgepal CO-730) does not alter the equilibrium constant for the formation of a complex (II) between 1,3,6,8-tetranitronaphthalene (I) and hydroxide ions in aqueous solutions. These effects have been dissected into those influencing the second-order rate constant for the formation, k1, and the first-order rate constant for the decomposition, k–1, of complex (II). Micellar effects are primarily on k1[k1(CTAB)/k1 0= 36, k1 0/k1(NaLS)= 43, k0 –1/k–1(CTAB)= 2·8, and k0 –1/k–1(NaLS)ca. 1]. Kinetic data on the effects of surfactant concentration on k1 gave the binding constants between (I) and CTAB (1·9 × 105| mol–1), between (I) and NaLS (3·6 × 103| mol–1), and between (II) and CTAB (3·9 × 105 l mol–1). The nature of these micellar effects are discussed in terms of electrostatic interactions and are related to analogous micellar effects on nucleophilic aromatic substitutions.Keywords
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