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Hirshfeld surface analysis and spectroscopic and DFT studies of p-acetotoluidide and p-thioacetotoluidide

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Abstract

The Hirshfeld surface analysis, theoretical calculation, and IR and Raman spectra of p-acetotoluidide and p-thioacetotoluidide were reported. Hirshfeld surfaces and fingerprint plot have been used for visualizing, exploring, and quantifying intermolecular interactions in the crystal lattice of the title compounds. The packing of the molecules in the crystal structure of p-acetotoluidide and p-thioacetotoluidide forms the chains of N–H···O and N–H···S hydrogen bonds, respectively. The close contacts are also dominated by H···H and H···C/C···H interactions. The analysis of Hirshfeld surface has been well correlated with the spectroscopic studies. Theoretical calculations of the title compounds’ isolated molecule have been carried out using DFT at the B3LYP level.

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Acknowledgments

This work was founded by the grant of the Institute of Mechanized Construction and Rock Mining (No. 19-71/415-01/2014). All of the calculations were performed with the aid of hardware and software at the Wrocław Centre for Networking and Supercomputing WCSS, Wrocław, Poland.

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Authors and Affiliations

  1. Research Centre of Building Materials “Izolacja”, Building Materials Technologies Group, Institute of Mechanized Construction and Rock Mining, W. Korfantego 193A Street, 40-157, Katowice, Poland

    Wioleta Śmiszek-Lindert

  2. School of Pharmacy with Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia, Katowice, Poland

    Elżbieta Chełmecka

  3. Department of Statistics, Medical University of Silesia, 30 Ostrogórska Street, 41-200, Sosnowiec, Poland

    Elżbieta Chełmecka

  4. Institute of Building Materials and Structures, Faculty of Civil Engineering, Cracow University of Technology, 31-155, Cracow, Poland

    Anna Dudzińska

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  1. Wioleta Śmiszek-Lindert
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  2. Elżbieta Chełmecka
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  3. Anna Dudzińska
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Correspondence to Wioleta Śmiszek-Lindert.

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Śmiszek-Lindert, W., Chełmecka, E. & Dudzińska, A. Hirshfeld surface analysis and spectroscopic and DFT studies of p-acetotoluidide and p-thioacetotoluidide. Struct Chem 27, 1093–1106 (2016). https://doi.org/10.1007/s11224-015-0731-4

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  • DOI: https://doi.org/10.1007/s11224-015-0731-4

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