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Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole |
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| Authors: | Carmen Domene Patrick W Fowler |
| Institution: | a Physical and Theoretical Chemistry Laboratory, Oxford University, South Parks Road, Oxford OX1 3QZ, UK b Debye Institute, Organic Chemistry and Catalysis, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands c Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK |
| Abstract: | 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. |
| Keywords: | Aromaticity Ring currents Ab initio calculations |
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