Computational study on atom-economic alkyne hydrotelluration reaction using benchmarked ECP for Te

Geometry and energy calibration studies are done for arriving at a proper ECP for tellurium containing compounds. Among the various d-function included ECPs cc-pwCVTZ-PP and def2-TZVP give more reliable results. Non-catalytic and base/radical initiated hydrotelluration reactions are computationally...

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Bibliographic Details
Published in:Journal of molecular graphics & modelling 2020-11, Vol.100, p.107659-107659, Article 107659
Main Authors: Jayasree, Elambalassery G., Aswathy, Mohanan
Format: Article
Language:English
Subjects:
Calibration
ECP
Hydrotelluration
Regio- and stereoselectivity
Vinyl tellurides
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Summary:Geometry and energy calibration studies are done for arriving at a proper ECP for tellurium containing compounds. Among the various d-function included ECPs cc-pwCVTZ-PP and def2-TZVP give more reliable results. Non-catalytic and base/radical initiated hydrotelluration reactions are computationally studied using the calibrated def2-TZVP, with a special focus on the regio-and stereoselective formation of vinyl tellurides. The explored gas phase reaction mechanism indicates the addition of tellurol to unsaturated carbon-carbon triple bond via a concerted transition structure. Regioselectivity has been noticeably realized in presence of both base and radical mediated hydrotelluration leading to Markovnikov and anti-Markovnikov product respectively. [Display omitted] •Performance of various ECPs in geometry and energy calculation of tellurium containing compounds is analyzed. .•Calibrated def2-TZVP is used for analyzing the mechanistic aspects of alkyne hydrotelluration reaction. .•Base and radical mediated alkyne hydrotelluration regioselectively leads to MKV and AMKV product respectively.
ISSN:1093-3263
1873-4243
DOI:10.1016/j.jmgm.2020.107659