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An unusual substituent effect in a cycloaddition of an azolium ylide 1,3‐dipole: An inverted V‐shaped hammett plot
Author(s) -
Butler Richard N.,
Grogan Denise C.,
Burke Luke A.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340631
Subject(s) - substituent , chemistry , hammett equation , dipole , ylide , cycloaddition , imide , resonance (particle physics) , computational chemistry , stereochemistry , organic chemistry , reaction rate constant , atomic physics , physics , quantum mechanics , kinetics , catalysis
An unusual inverted V‐shaped Hammett plot has been observed for substituent effects at the N ‐terminus of 1,2,3‐triazolium‐1‐imide 1,3‐dipoles in cycloaddition reactions. Theoretical studies (3‐21G and 6‐31G) suggest strong resonance interactions separately stabilizing both ends of the dipole.