Detailed Reaction Mechanisms of 4-Pyridylboronic Acid and (N-Methyl)-4-Pyridinium Boronic Acid with D-Sorbitol in Aqueous Solution

Daisuke Kusuyama, Yuta Samukawa, Tomoaki Sugaya, Satoshi Iwatsuki, Masahiko Inamo, Hideo D. Takagi, Koji Ishihara

Research output: Contribution to journalArticle

Abstract

Kinetic measurements of the reactions of (N-methyl)-4-pyridinium boronic acid [(N−Me)-4-Py + B(OH) 2 ] and 4-pyridinium boronic acid [4-HPy + B(OH) 2 ] with D-sorbitol in aqueous solution were performed, and the reaction mechanisms were clarified in detail. Both reactions proceeded in one step; i. e., the intermolecular rate-determining step forming the 2,3-bicoordinate product was followed by the fast intramolecular step from the bicoordinate product to the 2,3,5-tricoordinate product. N-Methylation of 4-HPy + B(OH) 2 was found to dramatically reduce the reactivity of the N-methylated-4-pyridinium boronate ion [(N−Me)-4-Py + B(OH) 3 ], although it had little effect on the reactivity of (N−Me)-4-Py + B(OH) 2 . The reaction rates were enhanced by ion-pair formation between the boronate ion and the protonated buffer cation.

Original languageEnglish
Pages (from-to)4944-4951
Number of pages8
JournalChemistrySelect
Volume4
Issue number17
DOIs
Publication statusPublished - 2019 May 8

Keywords

  • (N-Methyl)-4-pyridiniumboronic acid
  • 4-pyridinium boronic acid
  • D-sorbitol
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

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