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Issue 15, 2013
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Steric, hydrogen-bonding and structural heterogeneity effects on the nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride in ionic liquids

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Abstract

The nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride was investigated using water and a range of alcoholic nucleophiles in ionic liquid solvents. The reactivity patterns across the nucleophiles examined could be attributed to steric factors, which mediated the relative nucleophilicities. Reducing the hydrogen-bond acidity of the ionic liquid cation was found to generally increase the rate of reaction, however, the magnitude of this rate effect could be influenced by the steric bulk of the nucleophile and the structural heterogeneity of the ionic liquid. Preferential solvation phenomena in binary mixtures of ionic liquids were examined and suggest that the mechanism behind the hydrogen-bond solvation phenomenon arises from direct cation-mediated, rather than indirect anion-mediated, effects.

Graphical abstract: Steric, hydrogen-bonding and structural heterogeneity effects on the nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride in ionic liquids

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Publication details

The article was received on 18 Jan 2013, accepted on 21 Feb 2013 and first published on 22 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB40105G
Citation: Org. Biomol. Chem., 2013,11, 2534-2542
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    Steric, hydrogen-bonding and structural heterogeneity effects on the nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride in ionic liquids

    C. C. Weber, A. F. Masters and T. Maschmeyer, Org. Biomol. Chem., 2013, 11, 2534
    DOI: 10.1039/C3OB40105G

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