Ionization of carbon acids in liquid ammonia

Pengju Ji; Nicholas T. Powles; John H. Atherton; Michael I. Page

doi:10.1021/ol2026153

Ionization of carbon acids in liquid ammonia

Pengju Ji, Nicholas T. Powles, John H. Atherton, Michael I. Page

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12 Citations (Scopus)

Abstract

The acidities of various carbon acids in liquid ammonia (LNH ₃) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK _as in LNH ₃ with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK _a of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Brønsted β _nuc = 0.38.

Original language	English
Pages (from-to)	6118-6121
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	22
DOIs	https://doi.org/10.1021/ol2026153
Publication status	Published - 18 Nov 2011

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Ji, P., Powles, N. T., Atherton, J. H., & Page, M. I. (2011). Ionization of carbon acids in liquid ammonia. Organic Letters, 13(22), 6118-6121. https://doi.org/10.1021/ol2026153

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abstract = "The acidities of various carbon acids in liquid ammonia (LNH 3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH 3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK a of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Br{\o}nsted β nuc = 0.38.",

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N2 - The acidities of various carbon acids in liquid ammonia (LNH 3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH 3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK a of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Brønsted β nuc = 0.38.

AB - The acidities of various carbon acids in liquid ammonia (LNH 3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pK as in LNH 3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pK a of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Brønsted β nuc = 0.38.

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10.1021/ol2026153

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