Skip to main content
SpringerLink
Log in

Local aromaticity in benzo- and benzocyclobutadieno-annelated anthracenes

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Considerations based on the energetics of cyclic conjugation in individual rings indicate that benzocyclobutadieno-annelation has the opposite effect on local aromaticity in benzenoid hydrocarbons to benzo-annelation. This finding is now tested and corroborated by density functional theory (DFT) calculations of the geometry of all benzo- and benzocyclobutadieno-annelated congeners of anthracene. The harmonic oscillator model of aromaticity (HOMA) and some similar (geometry-based) indices of local aromaticity are found to have the same dependence on the modes of annelation as the molecular-graph-based energy effects.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Balaban AT, Đurđević J, Gutman I, Jeremić S, Radenković S (2010) J Phys Chem A114:5870

    Google Scholar 

  2. Balaban AT, Gutman I, Jeremić S, Đurđević J (2011) Monatsh Chem 142:53

    Article  CAS  Google Scholar 

  3. Gutman I (2005) Monatsh Chem 136:1055

    Article  CAS  Google Scholar 

  4. Đurđević J, Radenković S, Gutman I, Marković S (2009) Monatsh Chem 140:1305

    Article  Google Scholar 

  5. Schaad LJ, Hess BA (1972) J Am Chem Soc 94:3068

    Article  CAS  Google Scholar 

  6. Gutman I, Furtula B, Balaban AT (2011) J Serb Chem Soc 76:733

    Article  CAS  Google Scholar 

  7. Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 13:3839

    Article  Google Scholar 

  8. Krygowski TM (1993) J Chem Inf Comput Sci 33:70

    CAS  Google Scholar 

  9. Krygowski TM, Cyranski MK (2001) Chem Rev 101:1385

    Article  CAS  Google Scholar 

  10. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Rev A.1, Gaussian Inc, Wallingford

  11. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  12. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  13. Vijayalakshmi KP, Suresh CH (2008) J Comput Sci 29:1808

    CAS  Google Scholar 

  14. Minkin VI, Glukhovtsev MN, Simkin BY (1994) Aromaticity and antiaromaticity: electronic and structural aspects. Wiley, New York

    Google Scholar 

  15. Schaad LJ, Hess BA (2001) Chem Rev 101:1465

    Article  CAS  Google Scholar 

  16. Stanger A (2009) Chem Commun 1939

Download references

Acknowledgments

The authors thank the Serbian Ministry of Science of Serbia for financial support through Grants No. 144015G and 172016.

Author information

Authors and Affiliations

  1. Texas A & M University at Galveston, Galveston, TX, 77551, USA

    Alexandru T. Balaban

  2. Faculty of Science, Institute of Chemistry, University of Kragujevac, Kragujevac, Serbia

    Ivan Gutman, Svetlana Marković & Dušica Simijonović

Authors
  1. Alexandru T. Balaban
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ivan Gutman
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Svetlana Marković
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dušica Simijonović
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ivan Gutman.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1159 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Balaban, A.T., Gutman, I., Marković, S. et al. Local aromaticity in benzo- and benzocyclobutadieno-annelated anthracenes. Monatsh Chem 142, 797–800 (2011). https://doi.org/10.1007/s00706-011-0531-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0531-5

Keywords

Search

Navigation