1996
DOI: 10.1021/js960031l
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Solvent Effects on Chemical Processes. 11. Solvent Effects on the Kinetics of Decarboxylative Dechlorination of N-Chloro Amino Acids in Binary Aqueous—Organic Solvents

Abstract: The phenomenological theory of solvent effects is extended to chemical reaction rates and is tested against experimental data on the decarboxylative dechlorination of N-chloroalanine and N-chloroleucine at 25 degrees C in binary aqueous-organic solvent mixtures. The organic cosolvents studied were methanol, ethanol, l-propanol, 2-propanol, ethylene glycol, propylene glycol, acetonitrile, and dioxane. Reaction rates increased in all cosolvent systems. The kinetic solvent effects could be quantitatively describe… Show more

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Cited by 8 publications
(1 citation statement)
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“…The simplicity of the mechanism involved in the decarboxylation of N-Cl-a-amino acids has been used to test the phenomenological theory of solvent effects on chemical reaction rates. 22 At lower pH values, N-halo-a-amino acids can also occur in three protonation states, other than the anionic. Grob fragmentation is observed for such species if they are derived from secondary amino acids, in which case the disproportionation (Section 2.2) becomes rather slow.…”
Section: Grob Fragmentationmentioning
confidence: 99%
“…The simplicity of the mechanism involved in the decarboxylation of N-Cl-a-amino acids has been used to test the phenomenological theory of solvent effects on chemical reaction rates. 22 At lower pH values, N-halo-a-amino acids can also occur in three protonation states, other than the anionic. Grob fragmentation is observed for such species if they are derived from secondary amino acids, in which case the disproportionation (Section 2.2) becomes rather slow.…”
Section: Grob Fragmentationmentioning
confidence: 99%