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The reaction rates of the sodium methoxide-catalysed condensation of benzaldehyde and thiophene-2-carbaldehyde with heteroaromatic acetonitriles are measured in methanol.The reaction is third-order overall, first-order respect to each reactant.The reactant rates of thiophene-2-carbaldehyde with acetonitriles are lower than those of benzaldehyde indicating that the thienyl group behaves as an electron-donating substituent.The reactivity order with respect to acetonitriles is: 3-pyridylacetonitrile > thiophen-2-ylacetonitrile > phenylacetonitrile > thiophen-3-ylacetonitrile.From the Hammett treatment of the data of the reaction between benzaldehyde and acetonitriles the ? constants for the heteroatoms are obtained: ?alpha-S 0.30, ?beta-S -0.08, and ?beta-N 0.49.
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Reference：
Piperidine – Wikipedia,
Piperidine | C5H22219N – PubChem