119Sn NMR characterization, X-ray structural studies, and Hirshfeld surface analysis of organotin(IV) macroheterocycles synthesized by a Barbier approach via ultrasound activation

• Published in: Structural chemistry Vol. 35; no. 2; pp. 659 - 667
• Main Authors: García-González, J. Viridiana, Alvarado-Rodríguez, José G., Andrade-López, Noemí, Guerra-Poot, Cristian G., Martínez-Otero, Diego
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.04.2024; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Computer Applications in Chemistry; Magnesium; Molecular structure; NMR; Nuclear magnetic resonance; Oxygen atoms; Physical Chemistry; Single crystals; Structural analysis; Surface analysis (chemical); Theoretical and Computational Chemistry; Tin isotopes; Organotin compounds; Hirshfeld surfaces; Macroheterocycles; Barbier reaction
• ISSN: 1040-0400; 1572-9001
• DOI: 10.1007/s11224-023-02222-z

Two series of dinuclear organotin macroheterocycles of general formula [R 2 Sn{ Ch (C 6 H 4 CH 2 ) 2 } 2 SnR 2 ] [ Ch  = O with R =  n -Bu ( 2a ), Bn ( 3a ), Ph ( 4a ) and Ch  = S with R =  n -Bu ( 2b ), Bn ( 3b ), Ph ( 4b )] were easily synthetized by a Barbier-type reaction assisted by sonochemical activation of metallic magnesium. The 119 Sn{ 1 H} NMR data for all compounds and the X-ray single-crystal diffraction studies for 2a and 4a confirmed the presence of a central Sn atom in a four-coordinate environment. The molecular structures of 2a and 4a showed puckered 16-membered macroheterocycles. The tin and oxygen atoms are in the interior of the cavity of the macrocycle, surrounded by hydrophobic C–H bonds. A Hirshfeld surface analyses of 2a and 4a showed that the macrocycles are linked by weak C–H···π, C···C, and H···H non-covalent interactions. The pairwise interaction energies showed that the cohesion between the macrocycles are mainly due to dispersion forces.