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Extending the Family of N-Heterocyclic Heavy Carbene Analogues: Synthesis and Crystal and Molecular Structures of MeN[CH2C(O)N(R)]2Sn (R = Me2NCH2CH2, PhCH2, Me3CCH2)

Authors

  • Ljuba Iovkova-Berends,

    1. Lehrstuhl für Anorganische Chemie II der Technischen Universität, 44221 Dortmund, Germany Homepage: http://www.chemie.tu-dortmund.de/fb03/de/Forschung/AC/Jurkschat/index.html
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  • Miriam Seiger,

    1. Lehrstuhl für Anorganische Chemie II der Technischen Universität, 44221 Dortmund, Germany Homepage: http://www.chemie.tu-dortmund.de/fb03/de/Forschung/AC/Jurkschat/index.html
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  • Thomas Westfeld,

    1. CURRENTA Analytik, CHEMPARK, 51368 Leverkusen, Germany
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  • Alexander Hoffmann,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, 81377 München, Germany
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    • DFT calculations.

  • Sonja Herres-Pawlis,

    1. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5–13, 81377 München, Germany
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    • DFT calculations.

  • Klaus Jurkschat

    1. Lehrstuhl für Anorganische Chemie II der Technischen Universität, 44221 Dortmund, Germany Homepage: http://www.chemie.tu-dortmund.de/fb03/de/Forschung/AC/Jurkschat/index.html
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  • Dedicated to Professor Clemens Mügge on the occasion of his 60th birthday

Abstract

We report herein the synthesis of the N-methyl-NN″-diorganoiminodiacetic acid diamides MeN[CH2C(O)N(R)H]2 [3: R = Me2N(CH2)2; 4: R = PhCH2; 5: R = Me3CCH2] and the novel tin(II) derivatives MeN[CH2C(O)N(R)]2Sn [6: R = Me2N(CH2)2; 7: R = PhCH2; 8: R = Me3CCH2]. The compounds were characterized by elemental analyses, 1H NMR spectroscopy (35), solid-state 13C and 119Sn NMR spectroscopy (8), and single-crystal X-ray diffraction analysis (5, 8). Compound 8 shows intramolecular N→Sn and intermolecular O→Sn interactions with distances of 2.370(2) and 2.406(2) Å, respectively, the latter indicating that 8 is a coordination polymer. DFT calculations revealed covalent Sn–NC(O) and coordinative N→Sn and C=O→Sn bonds. The wB97Xd functional, which takes into account dispersive interactions, was employed for a correct theoretical description of, in particular, the latter bond.

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