Studies on Sulfate Esters. II. Carboxyl Group Catalysis in the Hydrolysis of Salicyl Sulfate

Stephen Benkovic

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The pH-rate profile for the hydrolysis of salicyl sulfate reveals hydronium ion and intramolecular carboxyl group catalysis. In contrast the rate of hydrolysis of p-carboxyphenyl sulfate is accelerated only by hydronium ion. The acid-catalyzed hydrolysis of aromatic sulfates is viewed as an A1 mechanism on the basis of activation entropies and D2O solvent isotope and substituent effects. Intramolecular carboxyl group participation is discussed in terms of general acid or specific acid nucleophilic catalysis and compared to other examples involving similar behavior including salicyl phosphate.

Original languageEnglish (US)
Pages (from-to)5511-5515
Number of pages5
JournalJournal of the American Chemical Society
Volume88
Issue number23
DOIs
StatePublished - Jan 1 1966

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Catalysis
Sulfates
Hydrolysis
Esters
Acids
Ions
Entropy
Isotopes
Phosphates
Chemical activation
hydronium ion

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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Studies on Sulfate Esters. II. Carboxyl Group Catalysis in the Hydrolysis of Salicyl Sulfate. / Benkovic, Stephen.

In: Journal of the American Chemical Society, Vol. 88, No. 23, 01.01.1966, p. 5511-5515.

Research output: Contribution to journalArticle

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