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Synthesis, Single Crystal Structure and Spectroscopic Aspects of Benzo[b]thiophene-3-carbaldehyde Based Chalcones

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Abstract

The present study highlights the synthesis, single crystal structure and complete spectral characterization of two heteroaryl chalcones, namely (i) (E)-3-(benzo[b]thiophen-3-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (C17H12O2S) and (ii) (E)-1-(2-aminophenyl)-3-(benzo[b]thio phen-3-yl)prop-2-en-1-one (C17H13NOS). In both of these compounds, the molecules show weak intermolecular C–H···O interactions utilizing the keto group in addition to hydrogen bonding including hydroxyl and amino groups. In the case of compound (ii) water molecules are trapped in voids of the crystal lattice. π–π stacking interactions between phenyl and benzothiazole rings are observed in the crystal packing. In addition to crystallographic data, both the structures are also described for the first time with 1H NMR, H–H Cosy, 13C NMR, DEPT-135, HR-MS, TGA-DTG, DSC, IR and UV spectral data.

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The synthesis, single crystal structure and complete spectral characterization of benzo[b]thiophene-3-carbaldehyde based novel heteroaryl chalcones.

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Acknowledgements

One of the authors Paresh N. Patel is thankful to Indian Institute of Technology Madras for the Institute post doctoral fellowship. Authors thank SAIF, IIT Madras for all the spectral analysis and Professor K. Venkatesan, Professor T. N. Guru Row, Mr. Amar, Indian Institute of Science, Bangalore and Professor N. Gautham, University of Madras, Chennai for their valuable discussions.

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Authors and Affiliations

  1. Laboratory of Bioorganic Chemistry, Department of Biotechnology, Indian Institute of Technology Madras, Chennai, Tamil Nadu, 600 036, India

    Paresh N. Patel & Anju Chadha

  2. National Center for Catalysis Research, Indian Institute of Technology Madras, Chennai, Tamil Nadu, 600 036, India

    Anju Chadha

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  1. Paresh N. Patel
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  2. Anju Chadha
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Correspondence to Anju Chadha.

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Patel, P.N., Chadha, A. Synthesis, Single Crystal Structure and Spectroscopic Aspects of Benzo[b]thiophene-3-carbaldehyde Based Chalcones. J Chem Crystallogr 46, 245–251 (2016). https://doi.org/10.1007/s10870-016-0653-z

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  • DOI: https://doi.org/10.1007/s10870-016-0653-z

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