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Approach toward the Understanding of Coupling Mechanism for EDC Reagent in Solvent-Free Mechanosynthesis

Author:
Wróblewska, Aneta, Paluch, Piotr, Wielgus, Ewelina, Bujacz, Grzegorz, Dudek, Marta K., Potrzebowski, Marek J.
Source:
Organic letters 2017 v.19 no.19 pp. 5360-5363
ISSN:
1523-7052
Subject:
X-radiation, X-ray diffraction, amides, amines, chemical reactions, chemical structure, differential scanning calorimetry, hydrochloric acid, nuclear magnetic resonance spectroscopy
Abstract:
A unique approach in mechanosynthesis, joining solid-state NMR spectroscopy, X-ray crystallography, and theoretical calculations, is employed for the first time to study the mechanism of the formation of the C–N amide bond using EDC·HCl as a coupling reagent. It has been proved that EDC·HCl, which in the crystal lattice exists exclusively in the cyclic form (X-ray data), easily undergoes transformation to a pseudocyclic stable intermediate in reaction with carboxylic acid forming a low-melt phase (differential scanning calorimetry, solid-state NMR). The obtained intermediate is reactive and can be further used for synthesis of amides in reaction with appropriate amines.
Agid:
5827003