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

Tetrahedron Letters

Volumn 46, Issue 23, 2005, Pages 4077-4080

  Domene, Carmen ^a   Jenneskens, Leonardus W ^b   Fowler, Patrick W ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UTRECHT UNIVERSITY   (Netherlands)

^c UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Ab initio calculations; Aromaticity; Ring currents

Indexed keywords

1,2 BENZISOXAZOLE; 2,1 BENZISOXAZOLE; BENZENE; BENZOXAZOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; OXAZOLE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CALCULATION; CIRCULATION; DENSITY; ISOMER; THERMODYNAMICS;

EID: 18844428628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.014     Document Type: Article

References (8)

1. M.K. Cyraňski, T.M. Krygowski, A.R. Katritsky, and P. von R. Schleyer J. Org. Chem. 67 2002 1333 1338
2. P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, and N.J.R. van Eikema Hommes J. Am. Chem. Soc. 118 1996 6317 6318
3. M.A.R. Matos, M.S. Miranda, V.M.F. Morias, and J.L. Liebman Eur J. Org. Chem. 2004 3340 3345
4. tot values: 1 -397.231996, 2 -397.255196, 3 -397.305473, 4 -244.594185, 5 -244.638741 and 6 (planar geometry), -398.272222 hartree
5. E. Steiner, and P.W. Fowler J Phys Chem A 105 2001 9553 9562
6. A. Soncini, R.W.A. Havenith, P.W. Fowler, L.W. Jenneskens, and E. Steiner J. Org. Chem. 67 2002 4753 4758
7. 5 The ability to sustain an anticlockwise diatropic current is taken as the signature of aromaticity in a cyclic molecule; in a similar way, a clockwise paratropic ring current corresponds to antiaromaticity. See for a recent review: Fowler, P. W.; Steiner, E.; Havenith, R. W. A.; Jenneskens, L. W. Magn. Reson. Chem. 2004, 42, S68-S78
8. E. Steiner, and P.W. Fowler Chem. Commun. 2001 2220 2221