3441-01-8Relevant articles and documents
From 1,3-dicyanobenzene to 3-cyanobenzamide - Its molecular structure in the gas-phase and in the crystal
Janczak, Jan,Kubiak, Ryszard
, p. 13 - 21 (2003)
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.
Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes
Chen, Xuenian,Kang, Jia-Xin,Ma, Yan-Na,Miao, Yu-Qi
supporting information, p. 3595 - 3599 (2021/06/06)
Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.
One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine
Golub, Tatiana,Dou, Gui-Yuan,Zeng, Cheng-Chu,Becker, James Y.
supporting information, p. 7961 - 7964 (2019/10/11)
Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).