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Preparation and Reactivity of 4,4′-diaminostilbene-2,2′disulphonate

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Abstract

The precursor compound 4,4′-diaminostilbene-2,2′disulphonic acid DAS-(SO3H)2 was successfully deprotonated through reactions with (n-Bu4N)(OH) and NaOH to produce the corresponding salts sodium 4,4′-diaminostilbene-2,2′disulphonate Na2(DAS-(SO3)2) (1) and tetrabutylammonium 4,4′-diaminostilbene-2,2′disulphonate (n-Bu4N)2(DAS-(SO3)2) (2). The structure of (n-Bu4N)2(DAS-(SO3)2) (2) was confirmed through the use of single crystal X-ray diffraction. Compound (2) crystallizes in the monoclinic space group P21/n with the lattice parameters of a = 10.0645(6), b = 14.2573(9), c = 17.6053(11), and β = 94.3160(10). The reaction of Cu2+(aq) with (n-Bu4N)2(DAS-(SO3)2) resulted in the crystallization of the molecular organocopper cluster, [CuDAS-(SO3)2]2·3H2O (3), that resembles a molecular parallelogram as revealed by single crystal X-ray diffraction. Compound (3) crystallizes in the monoclinic space group P21/n with the lattice parameters of a = 8.8647(6), b = 10.5247(7), c = 21.2265(14), and β = 93.1730(10). Within the structure of (3) each [DAS-(SO3)2]2− ligand is shown to bind two copper atoms through interactions with three of the five available metal binding sites.

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Preparation and Reactivity of 4,4′-diaminostilbene-2,2′disulphonate

Natalie C. Rader, Heather A. Nees, Paul S. Szalay*, Matthias Zeller and Allen D. Hunter

The preparation of 4,4′-diaminostilbene-2,2′disulphonic and its reactivity with copper(II) are described.

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Acknowledgements

MZ was supported by NSF grant 0111511, CLP by ACS PRF grant 37228-B3, JCW by ACS PRF grant 37228-B3-SRF, and the diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU.

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Authors and Affiliations

  1. Department of Chemistry, Muskingum College, 163 Stormont St, New Concord, OH, 43762, USA

    Natalie C. Rader, Heather A. Nees & Paul S. Szalay

  2. Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH, 44555, USA

    Matthias Zeller & Allen D. Hunter

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  1. Natalie C. Rader
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  2. Heather A. Nees
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  3. Paul S. Szalay
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  4. Matthias Zeller
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  5. Allen D. Hunter
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Correspondence to Paul S. Szalay.

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Rader, N.C., Nees, H.A., Szalay, P.S. et al. Preparation and Reactivity of 4,4′-diaminostilbene-2,2′disulphonate. J Chem Crystallogr 37, 609–614 (2007). https://doi.org/10.1007/s10870-007-9218-5

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  • DOI: https://doi.org/10.1007/s10870-007-9218-5

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