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

• Type: Article in International Scientific Journal
• Date: 2003

Authors

Matos, MAR (Author) FCUP; Miranda, MS (Author) Other; Morais, VMF (Author) Other; Liebman, JF (Author) Other

Journal

Title: Organic and Biomolecular Chemistry

Vol. 1

Pages: 2566-2571

ISSN: 1477-0520

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 29 Citations

Scopus - 28 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-000-K8W

DOI: 10.1039/b304405j

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 6