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Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide

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Abstract

Bis(2-amino-5-fluoro-3-methylphenyl)disulfide was obtained by oxidation of 2-amino-5-fluoro-3-methylbenzenethiol and was characterized by elemental analysis, IR and 1H-NMR spectroscopy. The X-ray structure was determined. Crystal data: C14H14N2F2S2: Monoclinic, P21 /n, a = 11.8268(3), b = 9.5770(3), c = 12.3977(3) Å, β = 98.079(2)°, V = 1390.29(7) Å, Z = 4. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.

Index Abstract

Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide

J. E. Drake1, M. B. Hursthouse2, M. E. Light2, R. Maheshwari3, K.G. Ojha3, R. Ratnani3*

Bis(2-amino-5-fluoro-3-methylphenyl)disulfide is linked into a three-dimensional frame work by a combination of intermolecular N–H···F and N–H···N and intramolecular N–H···S hydrogen bonds. The supramolecular structure arises because the NH2 groups form three center S···H···F hydrogen bonds and two center N–H···F and N–H···S hydrogen bonds.

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Acknowledgments

RM is grateful to CSIR, New Delhi for financial support. M.B.H. thanks the UK Engineering and Physical Sciences Council for support of the X-ray facilities at Southampton. J.E.D. thanks the University of Windsor for financial support.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, Canada, N9B 3P4

    J. E. Drake

  2. Department of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK

    M. B. Hursthouse & M. E. Light

  3. Department of Pure & Applied Chemistry, M.D.S. University, Ajmer, 305 009, India

    R. Maheshwari, K. G. Ojha & R. Ratnani

Authors
  1. J. E. Drake
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  2. M. B. Hursthouse
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  3. M. E. Light
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  4. R. Maheshwari
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  5. K. G. Ojha
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  6. R. Ratnani
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Correspondence to R. Ratnani.

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Drake, J.E., Hursthouse, M.B., Light, M.E. et al. Inter- and Intra-Molecular Hydrogen Bonding in Bis(2-amino-5-fluoro-3-methylphenyl)disulfide. J Chem Crystallogr 38, 553–556 (2008). https://doi.org/10.1007/s10870-008-9353-7

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  • DOI: https://doi.org/10.1007/s10870-008-9353-7

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