1502830-49-0Relevant academic research and scientific papers
Extending the family of N-heterocyclic heavy carbene analogues: Synthesis and crystal and molecular structures of MeN[CH2C(O)N(R)] 2Sn (R = Me2NCH2CH2, PhCH 2, Me3CCH2)
Iovkova-Berends, Ljuba,Seiger, Miriam,Westfeld, Thomas,Hoffmann, Alexander,Herres-Pawlis, Sonja,Jurkschat, Klaus
, p. 5836 - 5842 (2013)
We report herein the synthesis of the N-methyl-N′N″- 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[CH 2C(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 (3-5), 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) A, 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. A novel type of intramolecularly coordinated N-heterocyclic diazastannylene is reported that holds great potential for subsequent chemistry due to its high stability in air and the many possibilities to vary the substituents.
