Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation.
This paper reports the results of our thermochemical/calorimetric determination of the enthalpies of combustion, phase change, and formation of isatin, isatoic anhydride, and N-methylisatin. The density functional calculations accompanied by vibrational and thermal corrections were also performed for these compounds and N-methylisatoic anhydride. Through a combination of theoretical calculations and associated isodesmic reactions, we have deduced that isatin has some antiaromatic character and isatoic anhydride enjoys some aromatic stabilization.
Matos
M Agostinha R
MA
Centro de Investigação em Química, Departamento de Química, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal. marmatos@fc.up.pt
Miranda
Margarida S
MS
Morais
Victor M
VM
Liebman
Joel F
JF