Investigating the structural chemistry of organotin(IV) compounds: recent advances

Abstract

Organotin(IV) compounds have been considered for their outstanding industrial, medical and specific applications in the synthesis of various types of chemical compounds. In this review, we have focused on the structural chemistry of organotin(IV) compounds, including coordination chemistry, the effect of structure on reactions, bond formations from the perspective of structure and investigation of the structure of organotin(IV) compounds in different phases. The structural chemistry of organotin(IV) compounds is subject to interest due to their major impact on predicting the properties and drumming up support for pushing back the frontiers of synthesis of organotin(IV) compounds with advanced properties.

Formation of Dimethyl Carbonate from CO2 and Methanol Catalyzed by Me2SnO: A Density Functional Theory Approach

“…As proposed for formation of the first DMC by Miyake et al, the initial step is the rotation of the carbonate site, forming the complex 26. The activation barrier for this rotation should be similar to that commented above for rotation in the intermediate dimer Me 2 Sn(OMe)(OC(O)OMe 2 (19). 27 In the complex 26, the carbon atom of the carbonyl group is more electrophilic, favoring the attack by methanol, forming species 27, with a tetrahedral carbon.…”

“…This was confirmed by IRC calculations starting from the respective transition structures. The stationary point [Me 2 Sn-(OMe)(OC(O)OMe)] 2 (19) is the key intermediate for the formation of DMC and was identified previously by X-ray crystallography. 24 The energy profile identified in the present work agrees with previous computational studies of Miyake et al 27 and de Souto et al 28 As was the case for the methanol activation, the potential energy surface in the implicit solvent (bold) shows higher relative energies than in the gas phase (lightface) due to solvent stabilization of the charge polarization, disfavoring the CO 2 insertion into the complex.…”

“…17,23 In solution, these species tend to form dimers, with OH or OR as bridge groups between the monomers. 19 The first Sn alkoxide employed for DMC synthesis was Me 2 Sn(OMe) 2 , the simplest alkoxytin compound for this reaction. 24 These initial uses of the organotin and respective intermediates stimulated further studies to ascertain the proposed catalytic cycle for homogeneous catalysis in DMC synthesis (Scheme 2).…”

“…Sn-based catalysts present large applicability and efficiency. ,, Their catalytic activity is based on two principles: increased nucleophilicity of methoxy groups by stannylation and/or increased electrophilicity due the Lewis acid character of the Sn center . The use of Sn (IV) alkoxides (R 2 Sn­(OR) 2 ) and oxides (R 2 SnO) in the direct DMC synthesis has been described since the 90s. , The key for the effectiveness of these processes is the organotin capacity to absorb CO 2 and form the final product .…”

Glutamine conjugated organotin(IV) Schiff base compounds: Synthesis, structure, and anticancer properties

“…[ 2 ] During the last few decades, organotin(IV) compounds have been outshined for their exceptional structural and chemical properties and a broad range of applications in the agriculture industry, food industry, and medical science. [ 3,4 ] This has encouraged and nudged researchers towards developing a series of organotin compounds with the characteristic anti‐bacterial/anti‐fungal, anti‐leishmanial and antitumor properties. [ 5–7 ] Some of the organotin(IV) compounds have been reported for their remarkable antitumor properties, even better than cisplatin, which is of considerable importance in the field of organometallic oncology.…”