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Experimental and DFT studies for substituent effects on cycloadditions of C,N-disubstituted nitrones to cinnamoyl piperidine

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Title Experimental and DFT studies for substituent effects on cycloadditions of C,N-disubstituted nitrones to cinnamoyl piperidine
 
Creator Mandal, Sutapa
Maiti, Kaustabh K
Banerji, Avijit
Prangé, Thierry
Neuman, Alain
Acharjee, Nivedita
 
Subject Cycloadditions
Computational chemistry
Density functional theory
Activation energy
Transition state
 
Description 108-119
Cycloaddition reactions of <em>C</em>-aryl-<em>N</em>-methyl nitrones (with varied electron demand character) to cinnamoyl piperidines have been studied by both experimental and theoretical approaches. The reactions are completely regioselective.<em> Endo</em>/<em>meta</em> selectivity of the major isomer has been confirmed on the basis of UV-Vis, IR, NMR and X-ray studies. Global properties of the reactants have been analyzed. Delocalization and activation energies of the located transition states have been calculated. Concerted mechanism of the reactions has been confirmed from trajectory simulations. Computational studies have rationalized the preferred <em>endo</em> stereoselectivity and have also indicated that increase in electron withdrawing character of nitrone <em>C</em>-aryl substituent decreases the activation energies and increases the diastereomeric excess along the reaction pathway.
 
Date 2018-01-11T10:00:58Z
2018-01-11T10:00:58Z
2018-01
 
Type Article
 
Identifier 0975-0983(Online); 0376-4699(Print)
http://nopr.niscair.res.in/handle/123456789/43414
 
Language en_US
 
Rights <img src='http://nopr.niscair.res.in/image/cc-license-sml.png'> <a href='http://creativecommons.org/licenses/by-nc-nd/2.5/in' target='_blank'>CC Attribution-Noncommercial-No Derivative Works 2.5 India</a>
 
Publisher NISCAIR-CSIR, India
 
Source IJC-B Vol.57B(01) [January 2018]