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 | |
| Publication status | Published - 18 Nov 2011 |
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Ionization of carbon acids in liquid ammonia. / Ji, Pengju; Powles, Nicholas T.; Atherton, John H.; Page, Michael I.
In: Organic Letters, Vol. 13, No. 22, 18.11.2011, p. 6118-6121.Research output: Contribution to journal › Article
TY - JOUR
T1 - Ionization of carbon acids in liquid ammonia
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.
UR - http://www.scopus.com/inward/record.url?scp=80955155687&partnerID=8YFLogxK
U2 - 10.1021/ol2026153
DO - 10.1021/ol2026153
M3 - Article
VL - 13
SP - 6118
EP - 6121
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 22
ER -