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Extending the Family of N‐Heterocyclic Heavy Carbene Analogues: Synthesis and Crystal and Molecular Structures of MeN[CH 2 C(O)N(R)] 2 Sn (R = Me 2 NCH 2 CH 2 , PhCH 2 , Me 3 CCH 2 )
Author(s) -
IovkovaBerends Ljuba,
Seiger Miriam,
Westfeld Thomas,
Hoffmann Alexander,
HerresPawlis Sonja,
Jurkschat Klaus
Publication year - 2013
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201300535
Subject(s) - chemistry , intramolecular force , carbene , intermolecular force , tin , nuclear magnetic resonance spectroscopy , crystallography , crystal structure , stereochemistry , spectroscopy , single crystal , molecule , catalysis , organic chemistry , physics , quantum mechanics
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.