1974
DOI: 10.1021/ja00811a040
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Equilibrium acidities of carbon acids. II. Hydrocarbon indicators, phenylacetylene, and other carbon acids in the 20-27 pK region

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Cited by 39 publications
(23 citation statements)
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“…Relative to such indicators, therefore, 1-8 are expected to be several pAl units more acidic in the CsCHA system than in Me2SO, in complete analogy to the corresponding differences established for acetylenes. 24 In protic solvents, hydrogen bonding of the localized carbanions is undoubtedly more important than for delocalized carbanions. This additional solvation effect is in the same direction as the above ion-pair effect, such that p/Ts relative to delocalized carbanions are expected to be lower in protic solvents than in Me2SO and other polar aprotic solvents.…”
Section: Resultsmentioning
confidence: 99%
“…Relative to such indicators, therefore, 1-8 are expected to be several pAl units more acidic in the CsCHA system than in Me2SO, in complete analogy to the corresponding differences established for acetylenes. 24 In protic solvents, hydrogen bonding of the localized carbanions is undoubtedly more important than for delocalized carbanions. This additional solvation effect is in the same direction as the above ion-pair effect, such that p/Ts relative to delocalized carbanions are expected to be lower in protic solvents than in Me2SO and other polar aprotic solvents.…”
Section: Resultsmentioning
confidence: 99%
“…Gas phase PA [33] (kcal mol À1 ) pK b (experimental) pK b (calculated) |Error| Et 3 N 234.7 26.0 [35] 24.0 2.0 Pyrrolidine 226.2 23.9 [34] [36] 24.0 1.2 PA, proton affinity.…”
Section: Known Compoundmentioning
confidence: 99%
“…-NMR. : 1,14 (d, J = 6,5, 3H, CH3); 1,80 (m,20H,Cfiz); 2,26 (A-Teil von AB, J A B = 4, 1 H , CH2-CHCH3); 2,45 (s, 3H, CH3-CtjH4); ca . 2,45 (m,3 H , CH-0 (Epoxidj, B-Teil von A B , CHz-CHCH3) ; 2,93 (A -Teil von A B X , , J A B = 14, Jax = 5,5,113, 3.O~perztadeca~z-/~-ol (10) HELVETICA Cmnirca ACTA -1' 01.…”
Section: )mentioning
confidence: 99%
“…Darauf wurden noch 3,36 g (30 mniol) ICalium-t-butoxid zugegeben und weitcre 6 Std. bei = 7,2,46 (m,4 H , ; 2,63 (nz, 1 €1, CHCH3) ; 5,22 ( J t r a n s = 15,5, J,ic = 7, 1 €I, olcfini-3 H , CH3); 1,08-1,40 (WZ, 411, CH2); 1,40-1,73 (WZ, 2 H , CH2); 1,Y6-2,10 (~2 , 21.1, CHz-CI-I=CH); E-$-Muskenon (12) (C16H280, 4) aus 11. Ein Gemisch von 2,40 g (6,l mmol) des Hydroxysulfons 11, 1,02 g (9,1 mmol) Kalium-t-butoxid in 100 ml Toluol und 20 ml HMPA wurde 20 Std.…”
Section: )unclassified