Synthesis, characterization and coordination behavior of 2-(1-carboxyl-2-hydroxyphenyl)thiazolidine

Abstract

The reaction of 3-formylsalicylic acid with 2-aminoethanethiol produces 2-(1-carboxyl-2-hydroxyphenyl)thiazolidine (H₂chptz) which remains in equilibrium in solution with its corresponding Schiff base, 3-carboxysalicylidenethioethanolimine (H₃mcsalim) having an NSO-donor set of atoms. The reactions of the thiazolidine ligand with different metal salts leading to the synthesis of many new metal complexes and organometallic derivatives have been studied. For all the complexes the dianion of the Schiff base, H₃mcsalim acts as a tridentate NSO donor ligand. The reactions of [(Hmcsalim)Ti(π-C₅H₅)Cl] and [(Hmcsalim)Sn(Me)Cl], isolated in this study, with Me₃SiE (where, E stands for SMe, NMe₂ and C≡CPh) have also been studied. The elemental analyses, magnetic susceptibilities, molar conductance values, EPR-study, CV, molecular weights and spectroscopic (UV-Vis, IR, ¹H NMR) data characterize all the compounds under study. Based upon these data the geometry of the compounds has also been proposed.

Keywords:

• Schiff base
• Thiazolidine
• Organogroup(IV) compounds
• Organometallics
• Transition metals

Acknowledgements

This work is financially (partly) supported by the University of Kalyani. We are grateful to the Regional Sophisticated Instrumentation Centre, Central Drug Research Institute, Lucknow for elemental analyses and some spectroscopic measurements. Facilities provided by the Department of Science and Technology, Govt. of India, New Delhi under Funds for Improvement in Science and Technology are gratefully acknowledged.