Electrophilic substitution at saturated carbon. XXXVI. Correlations between rates of potassium methoxide catalyzed hydrogen-deuterium exchange reactions of carbon acids and H

Kollmeyer, Willy D.; Cram, Donald J.

doi:10.1021/ja01009a019

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Rate Depetidence On Acidity Fimctiotis1

Introduction1

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1969

1978

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Cited by 10 publications

(2 citation statements)

References 5 publications

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“…A number of rate-acidity fi~nction correlations have been recorded for base-induced reactions over the past few years (28)(29)(30)(34)(35)(36)(37). The log (rate) us.…”

Section: Rate Depetidence On Acidity Fimctiotismentioning

confidence: 99%

Base-catalyzed Isotopic Exchange of Molecular Hydrogen. II. Rate Dependence on Basicity in the Dimethyl Sulfoxide–Water System

Symons¹,

Buncel²

1973

Can. J. Chem.

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Isotopic exchange of D, has been determined in mixtures of dimethyl sulfoxide and water under catalysis by hydroxide ion. The rate of exchange increases by ca. lo4 as the medium composition is changed from 0% DMSO to 99.6% DMSO at 65 "C. The unusually low sensitivity to medium basicity is reflected in abnormally low slope values for the plots of log k,,, us. H-or J -. When [Me4NOH] is varied at a given medium composition, the apparent order with respect to [Me4NOH] is greater than unity.These results are discussed in terms of (1) rate determining proton transfer from D, to OH-with formation of hydride ion; (2)

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“…A number of rate-acidity fi~nction correlations have been recorded for base-induced reactions over the past few years (28)(29)(30)(34)(35)(36)(37). The log (rate) us.…”

Section: Rate Depetidence On Acidity Fimctiotismentioning

confidence: 99%

Base-catalyzed Isotopic Exchange of Molecular Hydrogen. II. Rate Dependence on Basicity in the Dimethyl Sulfoxide–Water System

Symons¹,

Buncel²

1973

Can. J. Chem.

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“…However, since the respect to the determination of the activation largest changes in these parameters take place parameters and isotope effects (1)(2)(3)(4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

Proton Transfer Reactions of Carbon Acids. III. Effect of Solvent Change on the Equilibrium and Kinetic Parameters of the Reaction of Di-(4-nitrophenyl)methane with Alkoxide Bases

Kim¹,

Leffek²

1973

Can. J. Chem.

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Proton Transfer Reactions in Highly Basic Media

Jones

1972

Progress in Physical Organic Chemistry

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Electrophilic substitution at saturated carbon. XXXVI. Correlations between rates of potassium methoxide catalyzed hydrogen-deuterium exchange reactions of carbon acids and H

Cited by 10 publications

References 5 publications

Base-catalyzed Isotopic Exchange of Molecular Hydrogen. II. Rate Dependence on Basicity in the Dimethyl Sulfoxide–Water System

Base-catalyzed Isotopic Exchange of Molecular Hydrogen. II. Rate Dependence on Basicity in the Dimethyl Sulfoxide–Water System

Proton Transfer Reactions of Carbon Acids. III. Effect of Solvent Change on the Equilibrium and Kinetic Parameters of the Reaction of Di-(4-nitrophenyl)methane with Alkoxide Bases

Proton Transfer Reactions in Highly Basic Media

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