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Title

The effect of perfluorination on the aromaticity of benzene and heterocyclic six-membered rings

AuthorsWu, J. I.; Pühlhofer, F. G.; Von Ragué Schleyer, P.; Puchta, R.; Kiran, B.; Mauksch, M.; Van Eikema Hommes, N. J. R.; Alkorta, Ibon ; Elguero, José
Issue Date2009
PublisherAmerican Chemical Society
CitationThe journal of physical chemistry, A, Molecules, spectroscopy, kinetics, environment & general theory 113: 6789- 6794 (2009)
AbstractDespite having six highly electronegative F's, perfluorobenzene C 6F6 is as aromatic as benzene. Ab initio block-localized wave function (BLW) computations reveal that both C6F6 and benzene have essentially the same extra cyclic resonance energies (ECREs). Localized molecular orbital (LMO)-nucleus-independent chemical shifts (NICS) grids demonstrates that the F's induce only local paratropic contributions that are not related to aromaticity. Thus, all of the fluorinated benzenes (C 6FnH(6-n), n = 1-6) have similar ring-LMONICSπzz values. However, 1,3-difluorobenzene 2b and 1,3,5-trifluorobenzene 3c are slightly less aromatic than their isomers due to a greater degree of ring charge alternation. Isoelectronic C5H 5Y heterocycles (Y = BH-, N, NH+) are as aromatic as benzene, based on their ring-LMO-NICSπzz and ECRE values, unless extremely electronegative heteroatoms (e.g., Y = O+) are involved. © 2009 American Chemical Society.
Publisher version (URL)http://dx.doi.org/10.1021/jp902983r
URIhttp://hdl.handle.net/10261/66273
DOI10.1021/jp902983r
Identifiersdoi: 10.1021/jp902983r
issn: 1089-5639
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