AN UNUSUAL SUBSTITUENT EFFECT IN A CYCLOADDITION OF AN AZOLIUM YLIDE 1,3-DIPOLE - AN INVERTED V-SHAPED HAMMETT PLOT

Authors
BUTLER RN GROGAN DC BURKE LA
Citation
Rn. Butler et al., AN UNUSUAL SUBSTITUENT EFFECT IN A CYCLOADDITION OF AN AZOLIUM YLIDE 1,3-DIPOLE - AN INVERTED V-SHAPED HAMMETT PLOT, Journal of heterocyclic chemistry, 34(6), 1997, pp. 1825-1827
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
6
Year of publication
1997
Pages
1825 - 1827
Database
ISI
SICI code
0022-152X(1997)34:6<1825:AUSEIA>2.0.ZU;2-Q
Abstract
An unusual inverted V-shaped Hammett plot has been observed for substi tuent effects at the N-terminus of 1,2,3-triazolium-1-imide 1,3-dipole s in cycloaddition reactions. Theoretical studies (3-21G and 6-31G) su ggest strong resonance interactions separately stabilizing both ends o f the dipole.