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Theoretical Evaluation of the Global and Local Electrophilicity Patterns to Characterize Hetero Diels‐Alder Cycloaddition in the Synthesis of Isoxazolo[4,5‐ e ](1,2,3,4‐tetrazine)
Author(s) -
SHARMA Pratibha,
KUMAR Ashok,
SINGH Jitendra,
SAHU Vinita
Publication year - 2009
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.200990146
Subject(s) - cycloaddition , chemistry , electrophile , reactivity (psychology) , reagent , computational chemistry , tetrazine , organic chemistry , catalysis , medicine , alternative medicine , pathology
A series of substituted dienophiles 1 – 10 and three 1,2‐diazadienes namely D ‐ 1 , D ‐ 2 , D ‐ 3 were chosen to understand the reactivity and selectivity of Diels‐Alder cycloaddition. The global and local electrophilicity patterns have been evaluated on a series of cycloaddition reactions to assess the reaction pathways (NDAC/IEDDAC) using the absolute scale of electrophilicity proposed by Parr et al. Regional electrophilicity at the active sites of the reagents involved in Diels‐Alder processes has been described on a quantitative basis using local or regional electrophilicity index i.e. Fukui function. Good qualitative/quantitative comparison was found between molecular energy gaps and global electronic parameters, which has been employed to assess the cycloaddition pathways successfully.