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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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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title = "Ionization of carbon acids in liquid ammonia",

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.",

author = "Pengju Ji and Powles, {Nicholas T.} and Atherton, {John H.} and Page, {Michael I.}",

year = "2011",

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AU - Ji, Pengju

AU - Powles, Nicholas T.

AU - Atherton, John H.

AU - Page, Michael I.

PY - 2011/11/18

Y1 - 2011/11/18

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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U2 - 10.1021/ol2026153

DO - 10.1021/ol2026153

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JO - Organic Letters

JF - Organic Letters

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