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

doi:10.1021/ol0156805

pK_a 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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

(equation presented) The pK_a 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 pK_a 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 language	English (US)
Pages (from-to)	1311-1314
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	9
DOIs	https://doi.org/10.1021/ol0156805
State	Published - May 3 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

author = "Wiskur, {Sheryl L.} and Lavigne, {John J.} and Hassan Ait-Haddou and Vincent Lynch and Chiu, {Yu Hung} and Canary, {James W.} and Anslyn, {Eric V.}",

year = "2001",

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doi = "10.1021/ol0156805",

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T1 - pKa values and geometries of secondary and tertiary amines complexed to boronic acids - Implications for sensor design

AU - Wiskur, Sheryl L.

AU - Lavigne, John J.

AU - Ait-Haddou, Hassan

AU - Lynch, Vincent

AU - Chiu, Yu Hung

AU - Canary, James W.

AU - Anslyn, Eric V.

PY - 2001/5/3

Y1 - 2001/5/3

N2 - (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.

AB - (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.

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

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

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