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)

Abstract

Abstract We report herein the synthesis of the N ‐methyl‐ N ′ N″ ‐diorganoiminodiacetic acid diamides MeN[CH 2 C(O)N(R)H] 2 [ 3 : R = Me 2 N(CH 2 ) 2 ; 4 : R = PhCH 2 ; 5 : R = Me 3 CCH 2 ] and the novel tin(II) derivatives MeN[CH 2 C(O)N(R)] 2 Sn [ 6 : R = Me 2 N(CH 2 ) 2 ; 7 : R = PhCH 2 ; 8 : R = Me 3 CCH 2 ]. The compounds were characterized by elemental analyses, 1 H NMR spectroscopy ( 3 – 5 ), solid‐state 13 C and 119 Sn 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.