Synthesis, X-Ray Crystallography, Theoretical Investigation and Optical Properties of 2-Chloro-N-(2,4-dinitrophenyl) Acetamide

2-Chloro-N-(2,4-dinitrophenyl) acetamide, 1, was synthesized and characterized by H-1 and C-13 NMR spectroscopy, ESI-MS, X-ray crystallography, and elemental analysis. This compound crystallizes in the monoclinic space group P2(1)/n. The crystal structure of compound 1 revealed the intramolecular H-bonding with the S(6) motif between H atom of the amide group and the nitro group at the ortho position. Several intermolecular C-H center dot center dot center dot O interactions hold different molecules of the compound 1 together resulting in the crystal packing. Red faint spots observed in the Hirshfeld surface of the compound 1 confirm the presence of N-H center dot center dot center dot O hydrogen bond as well as C-H center dot center dot center dot O interactions. According to the Hirshfeld surface, C-H center dot center dot center dot Cl interaction is also found, of which distance is relatively longer than the C-H center dot center dot center dot O distance. Moreover, the analysis of the corresponding fingerprint plots indicates the significant interactions within the crystal namely H center dot center dot center dot O/O center dot center dot center dot H (39.0%), C center dot center dot center dot O/O center dot center dot center dot C (10.6%), H center dot center dot center dot Cl/Cl center dot center dot center dot H (8.5%), H center dot center dot center dot H (7.3%), and H center dot center dot center dot C/C center dot center dot center dot H (5.9%) contacts. The optical properties of compound 1 in various solvents were investigated using UV-vis spectrophotometry. Compound 1 showed solvatochromic effects upon the varying polarity of the solvent. Time-dependent DFT calculations (TD-DFT) of compound 1 suggest that the deprotonation process occurs in polar solvents such as DMF. Graphic Crystal structure of 2-Chloro-N-(2,4-dinitrophenyl) acetamide (1) revealed the intramolecular N-HMIDLINE HORIZONTAL ELLIPSISO hydrogen bonding with the S(6) motif within the molecule as well as several intermolecular C-HMIDLINE HORIZONTAL ELLIPSISO interactions between molecules. Moreover, the compound 1 exhibited solvatochromic effects upon the varying polarity of the solvents. [GRAPHICS] .

Automated summary

Compound 1, 2-Chloro-N-(2,4-dinitrophenyl) acetamide, was synthesized and characterized using various methods such as H-1 and C-13 NMR spectroscopy, ESI-MS, X-ray crystallography, and elemental analysis. The crystal structure of compound 1 revealed the presence of intramolecular N-H···O hydrogen bonding and intermolecular C-H···O interactions. Compound 1 exhibited solvatochromic effects in different solvents, with time-dependent DFT calculations suggesting deprotonation in polar solvents like DMF.