Premium
Investigation into the Regiochemistry of 1,3‐Dipolar Cycloaddition of C , N ‐Diphenyl Nitrone with Some Vinyl Sulfoximines as Dipolarophile: Theoretical Studies
Author(s) -
Moeinpour Farid
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201180262
Subject(s) - regioselectivity , cycloaddition , nitrone , chemistry , 1,3 dipolar cycloaddition , computational chemistry , density functional theory , electrophile , reactivity (psychology) , nucleophile , organic chemistry , catalysis , medicine , alternative medicine , pathology
The regiochemistry of 1,3‐dipolar cycloaddition reactions of C , N ‐diphenyl nitrone with some vinyl sulfox‐ imines as dipolarophile was investigated using density functional theory (DFT)‐based reactivity indexes and activation energy calculations at B3LYP/6‐31G(d) level of theory. Analysis of the geometries and bond orders (BOs) at the TS structures associated with the different reaction pathways shows that these 1,3‐dipolar cycloaddition reactions occur via an asynchronous concerted mechanism. Analysis of the local electrophilicity and nucleophilicity indexes permits an interpretation about the regioselectivity of these 1,3‐dipolar cycloaddition reactions. The theoretical results obtained in the work clearly predict the regiochemistry of the isolated cycloadducts and agree to experimental outcomes.