engleski

Using desmotropes, cocrystals and salts for manipulating reactivity in mechanochemical organic reactions

Performing reactions in the solid state offers a largely unexplored possibility to influence reactivity by manipulating the solid form of the starting reactants. In this work, we explore the use of various solid forms of barbituric acid and its effect on reaction paths and kinetics in a Knoevenagel condensation reaction with vanillin. Modifications of barbituric acid included the use of its desmotrope, a cocrystal, and a salt as the starting reactant. Comparing these reactions with the reaction starting from the commercial keto-tautomer of barbituric acid, we find that the reaction kinetics could either be accelerated or slowed down, together with a change in the reaction mechanism. Exploring solid forms of reactants can be used as general methodology for manipulation of mechanochemical reactivity, further highlighting the strength of conducting reactions in the solid state, since many of the modifications of solids become unavailable upon dissolution.

mechanochemical reactivity ; barbituric acid ; Knoevenagel condensation ; desmtrope ; cocrystal ; salt ; reaction kinetics

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