Jump to main content
Jump to site search

Issue 19, 2015
Previous Article Next Article

Potentiometric determination of acid dissociation constants of novel biaryl monomers

Author affiliations

Abstract

The acid dissociation constants (pKas) of a number of novel polymerisable vinyl biaryl compounds, 4-(4′-ethenylphenyl)-pyridine (M1), 4′-ethenyl-(1,1′-biphenyl)-4-ol (M2), 4′-ethenyl-N,N-dimethyl-(1,1′-biphenyl)-3-amine (M3), 4′-ethenyl-(1,1′-biphenyl)-4-methanol (M4), 4′-ethenyl-N,N-dimethyl-(1,1′-biphenyl)-4-amine (M5), 4′-ethenyl-(1,1′-biphenyl)-4-carboxylic acid (M6), 4′-ethenyl-4-hydroxy-5-methyl-(1,1′-biphenyl)-3-carboxaldehyde (M7) were determined in a mixed solvent (THF–water) potentiometric titration at 25 °C and subsequent extrapolation to pure water via the Yasuda–Shedlovsky method. The acidity and basicity of the compounds in THF–water mixtures was observed to decrease with increasing THF fraction and is attributed to the corresponding decrease in the dielectric constant of the solution. To the best of our knowledge, this is the first reported study of pKa values undertaken for this class of compounds. The biaryls, M1–M7, were prepared by microwave-assisted Suzuki cross coupling of 4-vinylphenyl boronic acid with the appropriate aryl bromide and were custom designed for use as functional monomers in the synthesis of molecularly imprinted polymers.

Graphical abstract: Potentiometric determination of acid dissociation constants of novel biaryl monomers

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Jun 2015, accepted on 14 Aug 2015 and first published on 20 Aug 2015


Article type: Paper
DOI: 10.1039/C5AY01673H
Author version
available:
Download author version (PDF)
Anal. Methods, 2015,7, 8206-8211

  •   Request permissions

    Potentiometric determination of acid dissociation constants of novel biaryl monomers

    H. A. Zayas, A. McCluskey, M. C. Bowyer and C. I. Holdsworth, Anal. Methods, 2015, 7, 8206
    DOI: 10.1039/C5AY01673H

Search articles by author

Spotlight

Advertisements