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Reactivity of thiazolidine-2-thione towards CuI/CuII: Synthesis and structures of [3-(2-thiazolin-2-yl)thiazolidine-2-thione]copper(I) bromide and [bis(2,2′-bipyridine)nitratocopper(II)] nitrate

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Abstract

Thiazolidine-2-thione (L1, NC3H5S2) reacted with copper(I) bromide in CH3CN under aerobic conditions and transformed through C–S bond cleavage into 3-(2-thiazolin-2-yl)thiazolidine-2-thione (L2, C3H4S2N-C3H4SN). This thio-ligand L2 with CuI ion yielded a three coordinate complex, [3-(2-Thiazolin-2-yl)thiazolidine-2-thione]copper(I)bromide 1a which crystallized in the triclinic system with the space group P1 as reported earlier. Treatment of 1a with bis(diphenylphosphino)methane (dppm) in dichloromethane also formed [3-(2-thiazolin-2-yl)thiazolidine-2-thione]copper(I) bromide 1b but it crystallized into the triclinic system with a new space group, P-1: 296(2) K, a, 7.3890(19); b, 8.473(2); c, 9.491(2) Å; α, 70.273(5); β, 67.170(5); γ, 84.949(5)∘; R, 6.79%. Reactions of copper(II) nitrate with thiazolidine-2-thione followed by the addition of 2,2′-bipyridine or with 2,2′-bipyridine first followed by the addition of thiazolidine-2-thione, gave blue crystals in both the cases. The x-ray crystallography revealed stoichiometry of the complex formed as: [Cu(κ 2-N,N′-bipy)2(κ 1-ONO2)](NO3)2, which crystallized in monoclinic crystal system with space group, P21/n(14). Crystal data: 173(2) K, a, 11.318(1), b, 12.160(1), c, 14.967(1) Å; β = 98.01(1)∘, R, 3.99%; 296(2) K, a, 11.340(5), b, 12.249(5), c, 15.065(6) Å; β = 98.04(2)∘, R, 4.09%.

Thiazolidine-2-thione with copper(I) bromide in CH3CN under aerobic conditions yielded red brown crystals which on treatment with bis(diphenylphosphino)methane in dichloromethane formed [3-(2-thiazolin-2-yl)thiazolidine-2-thione]copper(I) bromide which crystallized into triclinic system with space group, P-1.

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Acknowledgements

Financial assistance in the form of Emeritus Scientist Grant [21(0904)/12-EMR-II] to T.S. Lobana, from the Council of Scientific and Industrial Research (CSIR), New Delhi, and from Department of Science and Technology (DST) for x-ray diffractometer grant to Department of Chemistry, GNDU, Amritsar are gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Guru Nanak Dev University, Amritsar, 143 005, India

    TARLOK S LOBANA, ANU RANI & AMANPREET K JASSAL

  2. Department of Chemistry, Keene State College, Keene, NH, 03435–2001, USA

    JERRY P JASINSKI

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  1. TARLOK S LOBANA
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Correspondence to TARLOK S LOBANA.

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Supplementary Information

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies of the data can be obtained free of charge on quoting the depository numbers CCDC 1006272 for 1b, 988896 for 2a and 988897 for 2b (Fax: + 44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk). (See Tables S1 and S2 for more details about nitrate coordination, complete bond lengths/angles for 2as well as for bonding trends of nitrate in presence of 2,2′-bipyridines).

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LOBANA, T.S., RANI, A., JASSAL, A.K. et al. Reactivity of thiazolidine-2-thione towards CuI/CuII: Synthesis and structures of [3-(2-thiazolin-2-yl)thiazolidine-2-thione]copper(I) bromide and [bis(2,2′-bipyridine)nitratocopper(II)] nitrate. J Chem Sci 127, 149–153 (2015). https://doi.org/10.1007/s12039-014-0760-3

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