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Formation and isomerization of dicyclopenta[de,mn]anthracene. Electronic Structure Study

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Abstract

The formation of dicyclopenta[de,mn]anthracene (P1) and its isomerization into dicyclopenta[jk,mn]phenanthrene (P3) was investigated using density functional theory. It was shown that P1 is formed from 1,4-diethynilanthracene, but due to its instability, it undergoes further transformation. This transformation involves rearrangements of some hydrogen atoms and ring contraction/ring expansion process, yielding as a final product the isomer P3. The energies of activation for the P1→P3 intraconversion show that this reaction is competitive to the other, previously investigated isomerization of P1 into dicyclopenta[de,kl]anthracene (P2). In addition, our investigation shows that the formation of P3 from P1 is energetically more favorable than the formation of P3 from P2. Thus, the presence of the isomer P3 in the reaction mixtures could also be caused by the isomerization of the very unstable isomer P1.

Isomerization of 1,4-diethynilanthracene to dicyclopenta[jk,mn]phenanthrene via dicyclopenta[de,mn]anthracene

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Acknowledgements

This work is supported by the Ministry of Science of Serbia, project No 144015G and 142025.

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Authors and Affiliations

  1. Faculty of Science, University of Kragujevac, P.O. Box 60, 34000, Kragujevac, Serbia

    Sonja Stanković, Svetlana Marković, Slavko Radenković & Ivan Gutman

Authors
  1. Sonja Stanković
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  2. Svetlana Marković
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  3. Slavko Radenković
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  4. Ivan Gutman
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Corresponding author

Correspondence to Sonja Stanković.

Electronic Supplementary Material

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ESM 1

Total energies, enthalpies, free energies (Table 1) and Cartesian coordinates for all computed species (I1, TS1, I2, TS2, I3, TS3, I4, TS4, P1, TS5, I5, TS6, I6, TS7, I7, TS8, and P3), IRC calculation for TS1 (Fig. 1) (DOC 214 KB)

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Stanković, S., Marković, S., Radenković, S. et al. Formation and isomerization of dicyclopenta[de,mn]anthracene. Electronic Structure Study. J Mol Model 15, 953–958 (2009). https://doi.org/10.1007/s00894-009-0453-x

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  • DOI: https://doi.org/10.1007/s00894-009-0453-x

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