Abstract
The interest in diphenyl ditelluride (Ph2Te2) is related to its strict analogy to diphenyl diselenide (Ph2Se2), whose capacity to reduce organic peroxides is largely exploited in catalysis and green chemistry. Since the latter is also a promising candidate as an antioxidant drug and mimic of the ubiquitous enzyme glutathione peroxidase (GPx), the use of organotellurides in medicinal chemistry is gaining importance, despite the fact that tellurium has no recognized biological role and its toxicity must be cautiously pondered. Both Ph2Se2 and Ph2Te2 exhibit significant conformational freedom due to the softness of the inter-chalcogen and carbon–chalcogen bonds, preventing the existence of a unique structure in solution. Therefore, the accurate calculation of the NMR chemical shifts of these flexible molecules is not trivial. In this study, a detailed structural analysis of Ph2Te2 is carried out using a computational approach combining classical molecular dynamics and relativistic density functional theory methods. The goal is to establish how structural changes affect the electronic structure of diphenyl ditelluride, particularly the 125Te chemical shift.
Highlights
Diphenyl ditelluride (Ph2 Te2 ) was first synthesized in 1894 [1,2,3]
Increasing the number of the functions resulted in a more accurate description of the PES of Ph2 Te2, which correctly returned both optimized structures with minimal relative energy differences. These results indicate that the main issue to consider in order to calculate a δ(125 Te) close to the experimental value is rooted in the accurate description of the molecular geometry and of the PES of Ph2 Te2 and all functionals perform quite
Relativistic density functional theory-based 125 Te-NMR calculations were performed using fully optimized conformers of Ph2 Te2 as well as on structures extracted from a classical molecular dynamics (MD) trajectory
Summary
Diphenyl ditelluride (Ph2 Te2 ) was first synthesized in 1894 [1,2,3]. Since the study on organotellurides has been rapidly increasing. Organotellurides are currently widely used in organic synthesis to obtain useful intermediates, e.g., via transmetallation or cross-coupling reactions, and in the interconversion of functional groups [6,7,8]. Ph2 Te2 proved to be efficient in catalytic oxidations of olefins [9]. In this reaction, the active catalyst is phenyl tellurol which forms upon Te–Te bond cleavage and can be oxidized to phenyltellurenic and phenyltellurinic acid. The chalcogen–chalcogen bond is soft and polarizable and can be broken [10], much more after initial oxidation, as reported for diphenyl diselenide (Ph2 Se2 ) [11,12]
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