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Synthesis and Crystal Structure Determination of 3-Phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one

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Abstract

A new type of substituted benzothiopyranone, 3-phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one, has been prepared by the condensation-acid cyclization of polylithiated phenylacetic acid phenylhydrazide with lithiated methyl thiosalicylate. Absorption spectra, especially 13C NMR, provided good indication of its structure, which was conclusively established with X-ray crystal structure analysis. In comparison to the few benzothiopyran X-ray reports documented, the benzothiopyranone ring of the molecule was found to be essentially planar, with the 3-phenyl ring nearly perpendicular to the benzothiopyranone fused-ring system. Crystals of C21H16N2OS are orthorhombic, P212121, a = 10.140(4) Å, b = 10.432(4) Å, c = 16.228(7) Å, Z = 4, V = 1717(1) Å3, R 1 = 0.0267 and wR 2 = 0.0725 for reflections with I > 2σ(I). The molecular packing in the crystal is the result of N–H···O hydrogen bonding.

Graphical Abstract

X-ray crystal analysis confirmed the structure of 3-phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one prepared by the condensation–cyclization of polylithiated phenylacetic acid phenylhydrazide with lithiated methyl thiosalicylate.

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Fig. 1
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Acknowledgements

We wish to thank the following sponsors: the Research Corporation, the National Science Foundation grants CHE # 9708014 and # 0212699 for Research at Undergraduate Institutions, the United States Department of Agriculture, NRICGP # 2003-35504-12853, and the Petroleum Research Fund, Administered by the American Chemical Society. The College of Charleston awarded summer grants through its Summer Undergraduate Research Forum (SURF-2006) to J. D. Knight.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC, 29424, USA

    Clyde R. Metz, John D. Knight, Stefan J. Pastine & Charles F. Beam

  2. Department of Chemistry, Clemson University, Clemson, SC, 29634, USA

    William T. Pennington

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  1. Clyde R. Metz
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  2. John D. Knight
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  3. Stefan J. Pastine
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  4. William T. Pennington
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  5. Charles F. Beam
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Correspondence to Charles F. Beam.

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Metz, C.R., Knight, J.D., Pastine, S.J. et al. Synthesis and Crystal Structure Determination of 3-Phenyl-2-(2-phenylhydrazino)-4H-1-benzothiopyran-4-one. J Chem Crystallogr 40, 536–540 (2010). https://doi.org/10.1007/s10870-010-9692-z

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