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<p>The p<i>K</i><sub>aH</sub> values of ten aliphatic amines, ranging from 9.8 to 11.5, have been measured in aqueous solution using an approach involving relative p<i>K</i><sub>aH</sub> measurements with <sup>1</sup>H NMR. The resulting scale (“ladder”) was anchored to reliable literature p<i>K</i><sub>aH</sub> values of two reference compounds: Me<sub>3</sub>N and Et<sub>2</sub>NH. An important finding of this work is that the p<i>K</i><sub>aH</sub> of <i>N,N</i>-diisopropylethylamine (DIPEA, Hünig’s base) is 11.44, ending the confusion in the literature, where the reported p<i>K</i><sub>aH</sub> values of this base have varied from 10 to 11.44.</p> Graphical Abstract <p><sup>1</sup>H NMR experimental study was carried out to determine reliable p<i>K</i><sub>aH</sub> estimates for ten aliphatic amines.</p> <p></p>

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Determination of pKaH Values of Amines in Water Using 1H NMR

  • 期刊论文

  • 发表日期：

    2025年10月28日

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  • Astrid Darnell,
  • Johan Lippus,
  • Lauri Toom,
  • Ivo Leito

摘要

The pKaH values of ten aliphatic amines, ranging from 9.8 to 11.5, have been measured in aqueous solution using an approach involving relative pKaH measurements with 1H NMR. The resulting scale (“ladder”) was anchored to reliable literature pKaH values of two reference compounds: Me3N and Et2NH. An important finding of this work is that the pKaH of N,N-diisopropylethylamine (DIPEA, Hünig’s base) is 11.44, ending the confusion in the literature, where the reported pKaH values of this base have varied from 10 to 11.44.

Graphical Abstract

1H NMR experimental study was carried out to determine reliable pKaH estimates for ten aliphatic amines.