Paradigms and paradoxes: en route to the understanding of the aromaticity of the "iso-species" isobenzofuran, anthranil, benzofurazan and 2,1,3-benzothiadiazole

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Margarida S Miranda (Author) FCUP; Agostinha A R Matos (Author) FCUP; Victor M F Morais (Author) ICBAS; Joel F Liebman (Author) Other

Journal

Title: Structural Chemistry

Vol. 23

Pages: 1241-1243

ISSN: 1040-0400

Publisher: Springer Nature

Indexing

ISI Web of Knowledge - 5 Citations

Scopus - 4 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-002-7Q3

DOI: 10.1007/s11224-012-9975-4

Abstract (EN): Using a model reaction, we recently investigated the thermochemistry and aromaticity systematics of nitrogen, oxygen and sulfur-containing heterocycles that are isoelectronic to the carbocyclic indane and its unsaturated counterpart indene. In this study all of the benzo-annelated species, e.g. indole, indoline, phthalic anhydride, phthalan and benzothiazole, all corresponding to annelation on a formal double bond of the 5-membered ring of the single ring species. In that study we asked "What is to be done about the so-called iso-species?" such as isobenzofuran, anthranil, benzofurazan and 2,1,3-benzothiadiazole, wherein it is annelation of the formal single bond in the 5-membered ring. A modified model reaction is suggested in the current paper where we admit that it is quantitatively untested.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 3