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Catalytic activity of tertiary amines with antisymbatic change of basic and nucleophilic properties in the chloroxypropylation reaction of acetic acid

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Abstract

The kinetic dependence of the reaction of (chloromethyl)oxirane ring-opening by acetic acid in the presence of tertiary amines R3N and RnNMe3−n has been studied. The orders of reaction with respect to acid and catalyst have been determined. The nucleophilicity of amines used has been measured in the quaternization reaction of R3N and RnNMe3−n by benzyl chloride (Menshutkin reaction). On the basis of correlations “amines structure–catalytic activity”, it has been shown that amines act as nucleophiles in this reaction.

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Authors and Affiliations

  1. Donetsk National University, Vinnytsia, Ukraine

    Stanislav Bakhtin, Yuliia Bespal’ko & Elena Shved

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  1. Stanislav Bakhtin
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  2. Yuliia Bespal’ko
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  3. Elena Shved
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Correspondence to Elena Shved.

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Bakhtin, S., Bespal’ko, Y. & Shved, E. Catalytic activity of tertiary amines with antisymbatic change of basic and nucleophilic properties in the chloroxypropylation reaction of acetic acid. Reac Kinet Mech Cat 119, 139–148 (2016). https://doi.org/10.1007/s11144-016-1051-4

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  • DOI: https://doi.org/10.1007/s11144-016-1051-4

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