Solvent Isotope Effects and Transition-State Solvation in the Basic Methanolysis of Esters

Tipo de material: Texto

TextoSeries ; Journal of the American Chemistry Society, 91, p.2045-1047, 1969Trabajos contenidos:

Mitton, C G
Gresser, M

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Resumen: Aryl methyl carbonates and aryl acetates undergo methoxide-catalyzed methanolysis in CH30D 1.5-2.1 times faster than in CH30H. The magnitudes of isotope effects and entropies of activation indicate that the gross isotope effects originate in an increase in structure of the solvent as methoxide ion partially adds to the substrate carbonyl groups, probably accompanied by an increase in solvent librational frequencies. The sub[1]stituent-induced variations in the isotope effects and entropies of activation are most easily interpreted as involving changes in hydrogen-bonding strength for solvent molecules.

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Artículo

Aryl methyl carbonates and aryl acetates undergo methoxide-catalyzed methanolysis in CH30D 1.5-2.1 times faster than in CH30H. The magnitudes of isotope effects and entropies of activation indicate that the gross isotope effects originate in an increase in structure of the solvent as methoxide ion partially adds to the substrate carbonyl groups, probably accompanied by an increase in solvent librational frequencies. The sub[1]stituent-induced variations in the isotope effects and entropies of activation are most easily interpreted as involving changes in hydrogen-bonding strength for solvent molecules.

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