Synthesis and structural characterization of 2-(−)-menthoxycarbonylethyltin compounds

• Published in: Polyhedron 2005-10, Vol.24 (15), p.2027-2034
• Main Authors: Tian, Lai-Jin, Sun, Yu-Xi, Liu, Xi-Jie, Yang, Guo-Ming, Shang, Zhi-Cai
• Format: Article
• Language: English
• Subjects: 2-(−)-Menthoxycarbonylethyltin; Ester tin; Intramolecular coordination; X-ray crystal structure
• ISSN: 0277-5387
• DOI: 10.1016/j.poly.2005.05.025

The title compounds, (−)-MenOCOCH 2CH 2SnCl n Ph 3- n ( n = 0, 1; 1, 2; 2, 3; 3, 4) and [(−)-MenOCOCH 2CH 2Sn(OH)Cl 2] 2 · 2(C 2H 5) 2O ( 5 · 2(C 2H 5) 2O) were synthesized and characterized by means of elemental analysis, IR, NMR ( 1H, 13C and 119Sn) and X-ray crystallography. Compounds 2– 5 · 2(C 2H 5) 2O contain intramolecular carbonyl-to-tin coordination, and the strengths of the interaction between the C O and Sn generally increase in order 1 < 2 < 3 < 4 < 5 · 2(C 2H 5) 2O. The title compounds, (−)-MenOCOCH 2CH 2SnCl n Ph 3− n ( n = 0, 1; 1, 2; 2, 3; 3, 4) and [(−)-MenOCOCH 2CH 2Sn(OH)Cl 2] 2 · 2(C 2H 5) 2O ( 5 · 2(C 2H 5) 2O) were synthesized and characterized by means of elemental analysis, IR and NMR ( 1H, 13C and 119Sn) spectra. The solid-state structures of the compounds 1, 3, 4 and 5 · 2(C 2H 5) 2O have been determined by X-ray diffraction methods. The tin atom in 1 possesses a distorted tetrahedral geometry with an intramolecular weak C O⋯Sn interaction of 3.342(4) Å. The compounds 3 and 4 have distorted trigonal bipyramidal geometry, in which there is an intramolecular carbonyl-to-tin coordination. The tin atom in 5 · 2(C 2H 5) 2O approximates to octahedral geometry via an intramolecular carbonyl-to-tin coordination and hydroxo-bridging. The strengths of the interaction between C O and Sn generally increase in the order 1 < 2 < 3 < 4 < 5 · 2(C 2H 5) 2O.