From 1,3-dicyanobenzene to 3-cyanobenzamide—its molecular structure in the gas-phase and in the crystal

Add time:08/14/2019    Source:sciencedirect.com

The crystals of 3-cyanobenzamide have been obtained in the reaction of MgPcH2O with 1,3-dicyanobenzene. 3-Cyanobenzamide crystallises in the P21/c space group of the monoclinic system with four molecules per unit cell. In the crystal, the 3-cyanobenzamide molecule is non-planar, the amide group is rotated by 21.8(1)° around the Car–Csp2 bond in relation to the phenyl ring. Full optimised molecular orbital calculations performed on the isolated 3-cyanobenzamide molecule have shown a similar conformation (the rotation angle equals to 22.46°). Two pairs of symmetric equivalent N–H⋯O and N–H⋯N hydrogen bonds with two neighbouring form pseudo one-dimensional chains interconnect each 3-cyanobenzamide molecule in the crystal. The chains of 3-cyanobenzamide molecules form a stacking structure with π⋯π interactions between the aromatic phenyl rings within the stacks. The molecular orbital calculations and conformational analysis have shown two equivalent pairs minimum of energy on the potential energy surface (PES)—one global, other local. During rotation of the amide group from 0 to 360° around the Car–Csp2 bond four rotation barriers are observed. The highest rotation barrier energy of 48.84 kJ mol−1 is compared to the hydrogen bond energy.

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