pKa values and geometries of secondary and tertiary amines complexed to boronic acids - Implications for sensor design

Sheryl L. Wiskur, John J. Lavigne, Hassan Ait-Haddou, Vincent Lynch, Yu Hung Chiu, James W. Canary, Eric V. Anslyn

Research output: Contribution to journalArticle

Abstract

(equation presented) The pKa values and the geometries of secondary and tertiary amines adjacent to boronic acids were determined using potentiometric and 11B NMR titrations. The studies showed that the secondary ammonium ion has a pKa similar to that of the tertiary ammonium species, which leads to the formation of tetrahedral boron centers at pH values above approximately 5.5. Therefore, secondary amines as well as tertiary amines, when placed proximal to boron centers, can be used to create tetrahedral boronic acids at neutral pH for diol complexation.

Original languageEnglish (US)
Pages (from-to)1311-1314
Number of pages4
JournalOrganic Letters
Volume3
Issue number9
DOIs
StatePublished - May 3 2001

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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