The use of FTIR and NMR spectroscopies to study prepolymerisation interactions in nitrogen heterocycles

Qendresa Osmani, Helen Hughes, Kevin Flavin, Jimmy Hedin-Dahlstrom, Christopher J. Allender, June Frisby, Peter McLoughlin

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A detailed investigation into the functional groups responsible for the formation of a noncovalent complex between 2-aminopyridine (template) and methacrylic acid (functional monomer) has been carried out using FTIR spectroscopy and confirmed by 1H NMR spectroscopic data. The approach adopted to confirm the mechanism of interaction was the analysis of the template plus the structurally similar 2-methylaminopyridine and 2-dimethylaminopyridine. A 1:1 stoichiometry of complexation was determined by Job plot analysis following titration, with FTIR results complementing those of the 1H NMR study. The strength of interaction between 2-aminopyridine and the functional monomer measured through band shifts by FTIR spectroscopy was compared with such interactions for the isomers 3- and 4-aminopyridine. This comparison identified a clear correlation between template pK a, degree of interaction and subsequent nonspecific binding in the nonimprinted polymer. Using FTIR spectroscopy it was also possible to observe the effect of temperature on the prepolymerisation solution. IR spectra showed that lower temperatures led to more stabilized interactions of the hydrogen-bonded complex. The potential advantages of FTIR spectroscopy compared with 1H NMR spectroscopy in studying prepolymerisation solutions have been identified.

Original languageEnglish
Pages (from-to)1229-1236
Number of pages8
JournalAnalytical and Bioanalytical Chemistry
Volume391
Issue number4
DOIs
Publication statusPublished - Jun 2008

Keywords

  • Aminopyridine
  • FTIR spectroscopy
  • Hydrogen bond
  • Molecularly imprinted polymers
  • Template-monomer interaction

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