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Syntheses and Structures of Diorganotin Compounds Containing a Pentadentate Schiff Base Featuring Two Chiral Centers
Author(s) -
Basu Baul Tushar S.,
Khatiwara Avishek,
Duthie Andrew,
Höpfl Herbert,
Mroß David,
Jurkschat Klaus
Publication year - 2025
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.202500164
A pentadentate Schiff base pro‐ligand, suitable for the generation of metal complexes containing two chiral centers, is synthesized. The pro‐ligand H 2 L Me is reacted with diorganotin precursors to yield the tin compounds [Me 2 Sn(L Me )] ( 1 ), [ n‐ Bu 2 Sn(L Me )] ( 2 ), [ t‐ Bu 2 Sn(L Me )] ( 3 ), [Bn 2 Sn(L Me )] ( 4 ), and [ n‐ Oct 2 Sn(L Me )] ( 5 ), where L Me = N ‐[( E )‐1‐[6‐[( E )‐ N ‐( p ‐tolylsulfonamido)‐ C ‐methylcarbonimidoyl]pyridin‐2‐yl]ethylideneamino]‐ p ‐tolylsulfonamide. Characterization in solution (NMR spectroscopy and high‐resolution mass spectrometry) and solid state (Fourier transform infrared spectroscopy and single crystal X‐ray diffraction analysis) confirms for each compound a seven‐coordinate C 2 SnN 3 O 2 environment with pentagonal‐bipyramidal geometry. The 119 Sn NMR spectra exhibit high field‐shifted signals, consistent with seven coordinated diorganotin Schiff base derivatives. In the solid state, the S(O)C 6 H 4 Me moieties in 1 – 4 are mutually anti ‐oriented, resulting in molecular topologies similar to those found in Jacobsen's catalyst. In addition to van der Waals interactions, the molecular arrangements in the 3D solid‐state structures are primarily controlled by CH⋯O hydrogen bonds, along with CH⋯N, CH⋯π, and π⋯π interactions giving macrocyclic or cage‐type assemblies.