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Edge modification of PAHs: the effect of embedded heterocycles on the aromaticity pattern

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Abstract

The NICS(1) values of the dibenzo[fg,ij]pentaphene system with embedded heteroatoms in the five-membered ring were calculated to explore the effect of the different heteroelements on the local aromaticities of the eight constituting rings. The calculated NICS(1) values in general are in accordance with Clar’s rule, while the local aromaticity in the five-membered ring correlates with that in the isolated rings. The NICS(1) aromaticities of the embedded six-membered ring span a nearly 10 ppm range with the variation of the heteroelement, correlating with the aromaticity of the neighbouring five-membered ring.

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Acknowledgments

This work is supported by Balaton PHC (830386K)—TÉT_12_FR-1-2013-0017; OTKA NN 113772; Campus France; TAMOP-4.2.1/B-09/1/KMR-2010-0002; and COST-STSM-CM1302 (SIPS).

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Authors and Affiliations

  1. Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szt. Gellért tér 4, Budapest, 1111, Hungary

    Rózsa Szűcs & László Nyulászi

  2. Institut des Sciences Chimiques de Rennes, UMR6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042, Rennes Cedex, France

    Rózsa Szűcs, Pierre-Antoine Bouit & Muriel Hissler

Authors
  1. Rózsa Szűcs
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  2. Pierre-Antoine Bouit
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  3. Muriel Hissler
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  4. László Nyulászi
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Corresponding authors

Correspondence to Muriel Hissler or László Nyulászi.

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Dedicated to Professor Magdolna Hargittai on the occasion of her 70th birthday.

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Szűcs, R., Bouit, PA., Hissler, M. et al. Edge modification of PAHs: the effect of embedded heterocycles on the aromaticity pattern. Struct Chem 26, 1351–1357 (2015). https://doi.org/10.1007/s11224-015-0665-x

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  • DOI: https://doi.org/10.1007/s11224-015-0665-x

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