pK(a) values and geometries of secondary and tertiary amines complexed to boronic acids-implications for sensor design

S L Wiskur; J J Lavigne; H Ait-Haddou; V Lynch; Y H Chiu; J W Canary; E V Anslyn

doi:10.1021/ol0156805

pK(a) values and geometries of secondary and tertiary amines complexed to boronic acids-implications for sensor design

Org Lett. 2001 May 3;3(9):1311-4. doi: 10.1021/ol0156805.

Authors

S L Wiskur¹, J J Lavigne, H Ait-Haddou, V Lynch, Y H Chiu, J W Canary, E V Anslyn

Affiliation

¹ Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.

PMID: 11348222
DOI: 10.1021/ol0156805

Abstract

[structure in text] The pK(a) values and the geometries of secondary and tertiary amines adjacent to boronic acids were determined using potentiometric and (11)B 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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amines / chemistry*
Boronic Acids / chemistry*
Crystallography, X-Ray
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Quaternary Ammonium Compounds / chemistry
Structure-Activity Relationship

Substances

Amines
Boronic Acids
Quaternary Ammonium Compounds