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

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Abstract

2-Chloro-N-(2,4-dinitrophenyl) acetamide, 1, was synthesized and characterized by 1H and 13C NMR spectroscopy, ESI–MS, X-ray crystallography, and elemental analysis. This compound crystallizes in the monoclinic space group P21/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⋯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⋯O hydrogen bond as well as C–H⋯O interactions. According to the Hirshfeld surface, C–H⋯Cl interaction is also found, of which distance is relatively longer than the C–H⋯O distance. Moreover, the analysis of the corresponding fingerprint plots indicates the significant interactions within the crystal namely H⋯O/O⋯H (39.0%), C⋯O/O⋯C (10.6%), H⋯Cl/Cl⋯H (8.5%), H⋯H (7.3%), and H⋯C/C⋯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 Abstract

Crystal structure of 2-Chloro-N-(2,4-dinitrophenyl) acetamide (1) revealed the intramolecular N–H⋯O hydrogen bonding with the S(6) motif within the molecule as well as several intermolecular C–H⋯O interactions between molecules. Moreover, the compound 1 exhibited solvatochromic effects upon the varying polarity of the solvents.

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Acknowledgements

This research is supported by the Thailand Research Fund (MRG 5580182), Kasetsart University Research and Development Institute, and Department of Chemistry, Kasetsart University, and the Center of Excellent for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education.

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Authors and Affiliations

  1. Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, 10900, Thailand

    Piangkwan Jansukra, Tanwawan Duangthongyou, Apisit Songsasean & Boontana Wannalerse

  2. Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Chatuchak, Bangkok, 10900, Thailand

    Worawat Wattanathana

  3. Synchrotron Light Research Institute (Public Organization), 111 University Avenue, Suranaree Sub-district, Muang, Nakhon Ratchasima, 30000, Thailand

    Suttipong Wannapaiboon

  4. Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, 10900, Thailand

    Songwut Suramitr

  5. Center for Advanced Studies in Nanotechnology for Chemical, Food and Agricultural Industries, KU Institute for Advanced Studies, Kasetsart University, Bangkok, 10900, Thailand

    Songwut Suramitr

  6. Supramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand

    Thawatchai Tuntulani

  7. Davenport Chemical Research Building, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada

    C. Scott Browning

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  1. Piangkwan Jansukra
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Jansukra, P., Wattanathana, W., Duangthongyou, T. et al. Synthesis, X-Ray Crystallography, Theoretical Investigation and Optical Properties of 2-Chloro-N-(2,4-dinitrophenyl) Acetamide. J Chem Crystallogr 51, 523–535 (2021). https://doi.org/10.1007/s10870-020-00875-w

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  • DOI: https://doi.org/10.1007/s10870-020-00875-w

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