Skip to main content
SpringerLink
Log in

The 'wired' universe of organic chemistry

  • Perspective
  • Published:

From Nature Chemistry

View current issue Submit your manuscript

Abstract

The millions of reactions performed and compounds synthesized by organic chemists over the past two centuries connect to form a network larger than the metabolic networks of higher organisms and rivalling the complexity of the World Wide Web. Despite its apparent randomness, the network of chemistry has a well-defined, modular architecture. The network evolves in time according to trends that have not changed since the inception of the discipline, and thus project into chemistry's future. Analysis of organic chemistry using the tools of network theory enables the identification of most 'central' organic molecules, and for the prediction of which and how many molecules will be made in the future. Statistical analyses based on network connectivity are useful in optimizing parallel syntheses, in estimating chemical reactivity, and more.

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

Figure 1: Construction and architecture of the network of organic chemistry.
Figure 2: Examples of synthetic pathways and synthetically challenging molecules identified by network analysis.
Figure 3: The universe of organic chemistry is a scale-free network evolving according to the mechanism of preferential attachment.
Figure 4: Network-based optimization of multiple syntheses and monitoring of restricted substances.

Similar content being viewed by others

References

  1. Tietze, L. F. & Beifuss, U. Sequential transformations in organic chemistry — a synthetic strategy with a future. Angew. Chem. Int. Ed. Engl. 32, 131–163 (1993).

    Article  Google Scholar 

  2. Corey, E. J. & Cheng, X.-M. The Logic of Chemical Synthesis (Wiley-Interscience, New York, 1995).

    Google Scholar 

  3. Nicolaou, K. C., Vourloumis, D., Winssinger, N. & Baran, P. S. The art and science of total synthesis at the dawn of the twenty-first century. Angew. Chem. Int. Ed. 39, 44–122 (2000).

    Article  CAS  Google Scholar 

  4. Fialkowski, M., Bishop, K. J. M., Chubukov, V. A., Campbell, C. J. & Grzybowski, B. A. Architecture and evolution of organic chemistry. Angew. Chem. Int. Ed. 44, 7263–7269 (2005).

    Article  CAS  Google Scholar 

  5. Bishop, K. J. M., Klajn, R. & Grzybowski, B. A. The core and most useful molecules in organic chemistry. Angew. Chem. Int. Ed. 45, 5348–5354 (2006).

    Article  CAS  Google Scholar 

  6. Albert, R. & Barabasi, A. L. Statistical mechanics of complex networks. Rev. Mod. Phys. 74, 47–97 (2002).

    Article  Google Scholar 

  7. Jeong, H., Tombor, B., Albert, R., Oltval, Z. N. & Barabasi, A. L. The large-scale organization of metabolic networks. Nature 407, 651–654 (2000).

    Article  CAS  Google Scholar 

  8. Albert, R., Jeong, H. & Barabasi, A. L. Diameter of the World-Wide Web. Nature 401, 130–131 (1999).

    Article  CAS  Google Scholar 

  9. Broder, A. et al. Graph structure in the Web. Comput. Netw. 33, 309–320 (2000).

    Article  Google Scholar 

  10. Amaral, L. A. N. & Ottino, J. M. Complex networks — Augmenting the framework for the study of complex systems. Eur. Phys. J. B 38, 147–162 (2004).

    Article  CAS  Google Scholar 

  11. Chemical Market Reporter: Chemical prices, 7 March 2005 http://www.chemicalmarketreporter.com.

  12. Allu, T. K. & Oprea, T. I. Rapid evaluation of synthetic and molecular complexity for in silico chemistry. J. Chem. Inf. Model. 45, 1237–1243 (2005).

    Article  CAS  Google Scholar 

  13. Faloutsos, M., Faloutsos, P. & Faloutsos, C. On power-law relationships of the internet topology. Comput. Commun. Rev. 251–262 (1999).

  14. Redner, S. How popular is your paper? An empirical study of the citation distribution. Eur. Phys. J. B 4, 131–134 (1998).

    Article  CAS  Google Scholar 

  15. Liljeros, F., Edling, C. R., Amaral, L. A. N., Stanley, H. E. & Aberg, Y. The web of human sexual contacts. Nature 411, 907–908 (2001).

    Article  CAS  Google Scholar 

  16. Kirkpatrick, S., Gelatt, C. D. & Vecchi, M. P. Optimization by simulated annealing. Science 220, 671–680 (1983).

    Article  CAS  Google Scholar 

  17. Fukui, K. & Fujimoto, H. Frontier Orbitals and Reaction Paths: Selected Papers of Kenichi Fukui (World Scientific, Singapore, 1997).

    Book  Google Scholar 

  18. Ugi, I. et al. Computer-assistance in the design of syntheses and a new generation of computer-programs for the solution of chemical problems by molecular logic. Pure Appl. Chem. 60, 1573–1586 (1988).

    Article  CAS  Google Scholar 

  19. Ugi, I. et al. Computer-assisted solution of chemical problems — the historical development and the present state-of-the-art of a new discipline of chemistry. Angew. Chem. Int. Ed. Engl. 32, 201–227 (1993).

    Article  Google Scholar 

  20. Anelli, P. L. et al. Molecular Meccano 1. [2]rotaxanes and a [2]catenane made to order. J. Am. Chem. Soc. 114, 193–218 (1992).

    Article  CAS  Google Scholar 

  21. Bissell, R. A., Cordova, E., Kaifer, A. E. & Stoddart, J. F. A chemically and electrochemically switchable molecular shuttle. Nature 369, 133–137 (1994).

    Article  CAS  Google Scholar 

  22. Iijima, T. et al. Controllable donor-acceptor neutral [2]rotaxanes. Chem.-Eur. J. 10, 6375–6392 (2004).

    Article  CAS  Google Scholar 

  23. Asakawa, M. et al. A chemically and electrochemically switchable [2]catenane incorporating a tetrathiafulvalene unit. Angew. Chem. Int. Ed. 37, 333–337 (1998).

    Article  CAS  Google Scholar 

  24. Amabilino, D. B. & Stoddart, J. F. Interlocked and intertwined structures and superstructures. Chem. Rev. 95, 2725–2828 (1995).

    Article  CAS  Google Scholar 

  25. Stoddart, J. F. & Colquhoun, H. M. Big and little Meccano. Tetrahedron 64, 8231–8263 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical and Biological Engineering, Northwestern University, 2145 Sheridan Road, Evanston, 60208, Illinois, USA

    Bartosz A. Grzybowski, Kyle J. M. Bishop, Bartlomiej Kowalczyk & Christopher E. Wilmer

  2. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, 60208, Illinois, USA

    Bartosz A. Grzybowski

Authors
  1. Bartosz A. Grzybowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kyle J. M. Bishop
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bartlomiej Kowalczyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Christopher E. Wilmer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bartosz A. Grzybowski.

Supplementary information

Supplementary information

Supplementary information (PDF 2710 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Grzybowski, B., Bishop, K., Kowalczyk, B. et al. The 'wired' universe of organic chemistry. Nature Chem 1, 31–36 (2009). https://doi.org/10.1038/nchem.136

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1038/nchem.136

  • Springer Nature Limited

This article is cited by

Search

Navigation