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Issue 14, 2003
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Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation

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Abstract

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.

Graphical abstract: Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation

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Publication details

The article was received on 25 Apr 2003, accepted on 02 Jun 2003 and first published on 18 Jun 2003


Article type: Paper
DOI: 10.1039/B304405J
Org. Biomol. Chem., 2003,1, 2566-2571

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    Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation

    M. A. R. Matos, M. S. Miranda, V. M. F. Morais and J. F. Liebman, Org. Biomol. Chem., 2003, 1, 2566
    DOI: 10.1039/B304405J

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