Abstract
The title mol-ecules were synthesized by the reaction of 4-substituted sodium benzoates with chloro-acetic acid amide in the presence of di-methyl-formamide. The yields of 2-amino-2-oxoethyl 4-bromo-benzoate, C9H8BrNO3, I, 2-amino-2-oxoethyl 4-nitro-benzoate, C9H8N2O5, II, and 2-amino-2-oxoethyl 4-amino-benzoate monohydrate, C9H10N2O3·H2O, III, are 86, 78 and 88%, respectively. The low yield of II is explained by the reduced reactivity of the mol-ecule 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 inter-molecular N-H⋯O hydrogen bonds are observed, but the mol-ecules differ in some torsion angles as well as in the dihedral angles between the mean planes of the benzene rings and the amide groups.
Highlights
The title molecules were synthesized by the reaction of 4-substituted sodium benzoates with chloroacetic acid amide in the presence of dimethylformamide
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
In all three crystal structures, the same type of intermolecular N—HÁ Á ÁO 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
Summary
Molecules containing an aromatic ring, a carboxyl and an amino group represent an important class of organic compounds and, with several reaction centers, they are important intermediates in industry They are often used as synthons in organic synthesis and are widely used as ligands in the coordination chemistry of various transition metals. The new crystalline compounds 2-amino-2-oxoethyl 4-bromobenzoate (I), 2-amino-2-oxoethyl 4-nitrobenzoate (II) and 2-amino-2-oxoethyl)-4-aminobenzoate monohydrate (III) (Fig. 1) were synthesized from the reaction of 4-substituted sodium benzoates with chloroacetic acid amide in the presence of dimethylformamide. Their structures were determined by X-ray crystallographic analysis
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