Crystal structures of 2-amino-2-oxoethyl 4-bromobenzoate, 2-amino-2-oxoethyl 4-nitrobenzoate and 2-amino-2-oxoethyl 4-aminobenzoate monohydrate

Abstract

The title molecules were synthesized by the reaction of 4-substituted sodium benzoates with chloroacetic acid amide in the presence of dimethylformamide. The yields of 2-amino-2-oxoethyl 4-bromobenzoate, C9H8BrNO3, I, 2-amino-2-oxoethyl 4-nitrobenzoate, C9H8N2O5, II, and 2-amino-2-oxoethyl 4-aminobenzoate monohydrate, C9H10N2O3·H2O, III, are 86, 78 and 88%, respectively. The low yield of II is explained by the reduced reactivity of the molecule in a nucleophilic exchange reaction because of the negative induction and negative mesomeric effects of the nitro group on the benzene ring. Single crystals were obtained from the products under the same (temperature and solvent) conditions. In the case of III, the crystals formed as a monohydrate. In all three crystal structures, the same type of intermolecular N—H...O hydrogen bonds are observed, but the molecules differ in some torsion angles as well as in the dihedral angles between the mean planes of the benzene rings and the amide groups.