2013 Volume 42 Issue 12 Pages 1508-1510
One of six 2-alkylamino-4,6-dimethylnicotinamides afforded a conglomerate, and subsequent X-ray crystallographic analysis revealed that the compound crystallized in the monoclinic system, the space group P21. Crystallization of the racemic nicotinamide from the melt led to the chiral breaking of symmetry from 83 to 92% ee. This amide exhibited considerably stable axial chirality (ΔG‡: 22.4–23.5 kcal mol−1 at 20 °C) due to rotationally restricted scaffolds for the C–C(=O) bond.
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