1964
DOI: 10.3891/acta.chem.scand.18-1043
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Nucleophilic Reactivity of Alkoxide Ions Towards 2,4-Dinitrofluorobenzene and the Acidity of Alcohols.

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Cited by 65 publications
(32 citation statements)
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“…Of the two proposed fGly catalyzed pathways, the S N 2-E2 mechanism requires only one high energy barrier S-O bond cleavage. The rate of the initial S N 2 step may be accelerated by the decreased p K a of the geminal diol hydroxyl group (e.g., acetaldehyde hydrate has a p K a of 13.57 33 ) compared to a conventional hydroxyl group (e.g., 15.93 34 ). A recent theoretical study has suggested that the initial nucleophilic attack of fGly-diol on substrate may be rate-determining, and not the subsequent elimination.…”
Section: Fgly Participates Directly In Sulfate Ester Hydrolysismentioning
confidence: 99%
“…Of the two proposed fGly catalyzed pathways, the S N 2-E2 mechanism requires only one high energy barrier S-O bond cleavage. The rate of the initial S N 2 step may be accelerated by the decreased p K a of the geminal diol hydroxyl group (e.g., acetaldehyde hydrate has a p K a of 13.57 33 ) compared to a conventional hydroxyl group (e.g., 15.93 34 ). A recent theoretical study has suggested that the initial nucleophilic attack of fGly-diol on substrate may be rate-determining, and not the subsequent elimination.…”
Section: Fgly Participates Directly In Sulfate Ester Hydrolysismentioning
confidence: 99%
“…Ethyl iodide should be less reactive with the organic-inorganic carbonate hybrid than methyl iodide, according to the SN 2 mechanism. There is greater steric hindrance with ethyl iodide and the electrophilic character of the alkyl group of ethyl iodide dissolved in ethanol is less marked than that of methyl iodide dissolved in methanol, due to the lower dissociation power of ethanol than of methanol [31]. However, the mixture of ethanol and ethyl iodide is swollen [40] by the CO 2 , increasing the reactivity of the different species, for example, the reactivity of EtOH with CO 2 and that of PEC with EtI.…”
Section: Carbon Dioxide Sequestration Into An Organic Carbonatementioning
confidence: 99%
“…For these reasons, carbon dioxide sequestration with ethanol is in keeping with most green chemistry principles. However, ethanol is less reactive than methanol, as it is less acidic [31].…”
Section: Introductionmentioning
confidence: 99%
“…Keto acids and hydroxyketones have the potential to engage in ring‐chain tautomerism. When the intramolecular nucleophilic attack of the carboxyl group in the keto acid at the carbonyl carbon occurs in the tautomerism (Figure b), the deprotonation of H4 in the inflexible ring can be caused by the influence on the production of the hemiketal due to the high p K a value for the alcohols (12–19). These interpretations are related to the mechanisms in the presence of base.…”
Section: Resultsmentioning
confidence: 99%