Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole

Journal article

Direct computation of the π-current density, that is, the 'ring current', of anthranil (1) and its isomers 1,2-benzisoxazole (2) and benzoxazole (3) reveals different patterns of current flow: isomers 2 and 3 sustain strong benzene-like currents in the six-membered and bifurcated flow in the five-membered ring, whereas, in keeping with its lower thermodynamic stability, 1 has only a perimeter circulation without separate monocycle currents. Although the ring current criterion does not offer a sharp distinction between 2 and 3, their difference in thermodynamic stability is identical to that between isoxazole (4) and oxazole (5) suggesting an aromaticity order 1 < 2 ≈ 3. © 2005 Elsevier Ltd. All rights reserved.

Authors: Domene, C; Jenneskens, L; Fowler, P

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 46
• Issue: 23
• Pages: 4077-4080
• Publication date: 2005-06-06
• DOI: 10.1016/j.tetlet.2005.04.014
• ISSN: 0040-4039
• Language: English
• Keywords: ab initio calculations; ring currents; aromaticity