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A Complete NCI Perspective: From New Bonds to Reactivity

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Applications of Topological Methods in Molecular Chemistry

Part of the book series: Challenges and Advances in Computational Chemistry and Physics ((COCH,volume 22))

Abstract

The Non-Covalent Interaction (NCI) index is a new topological tool that has recently been added to the theoretical chemist’s arsenal. NCI fills a gap that existed within topological methods for the visualization of non-covalent interactions. Based on the electron density and its derivatives, it is able to reveal both attractive and repulsive interactions in the shape of isosurfaces, whose color code reveals the nature of the interaction. It is interesting to note that NCI can even be calculated at the promolecular level, making it a suitable tool for big systems, such as proteins or DNA. Within this chapter we will review the main characteristics of NCI, its similarities with and differences from previous approaches. Special attention will be paid to the visualization of new interaction types. Being based on the electron density, NCI is not only very stable with respect to the calculation method, but it is also a suitable tool for detecting new bonding mechanisms, since all such mechanisms should have a detectable effect on the electron density. This type of approach overcomes the limitations of bond definition, revealing all interaction types, irrespective of whether they have a name or have previously been identified. Finally, we will show how this tool can be used to understand chemical change along a chemical reaction. We will show an example of torquoselectivity and put forward an explanation of selectivity based on secondary interactions which is complementary to the historical orbital approach.

Zeina Maroun can be contacted at zema@topsoe.dk

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Acknowledgments

This work undertaken (partially) in the framework of CALSIMLAB is supported by the public grant ANR-11-LABX-0037-01 overseen by the French National Research Agency (ANR) as part of the “Investissements d’Avenir” program (reference: ANR-11-IDEX-0004-02).

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Authors and Affiliations

  1. Laboratoire de Chimie Théorique, UPMC Univ Paris 06, UMR 7616, 75005, Paris, France

    Christophe Narth, Roberto A. Boto, Jean-Philip Piquemal & Julia Contreras-García

  2. Laboratoire de Chimie Théorique, CNRS, UMR 7616, 75005, Paris, France

    Christophe Narth, Roberto A. Boto, Jean-Philip Piquemal & Julia Contreras-García

  3. Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark

    Zeina Maroun

  4. Scienomics, 16 rue de l’Arcade, 75008, Paris, France

    Robin Chaudret

  5. Institut de Recherche de Chimie Paris, ENSCP, Ecole Nationale Superieure de Chimie de Paris Chimie ParisTech, UMR 8247, 75231, Paris, France

    Marie-Laure Bonnet

  6. Institut de Recherche de Chimie Paris, CNRS, UMR 8247, 75231, Paris, France

    Marie-Laure Bonnet

  7. Institut du Calcul et de la Simulation (ICS), Université Pierre et Marie Curie (UPMC), Paris VI, 75005, Paris, France

    Roberto A. Boto

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  1. Christophe Narth
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  2. Zeina Maroun
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  3. Roberto A. Boto
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Correspondence to Julia Contreras-García .

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Editors and Affiliations

  1. LCC-CNRS, Toulouse, France

    Remi Chauvin

  2. LCC-CNRS, Toulouse, France

    Christine Lepetit

  3. Théorique, UMR 761, Laboratoire de Chimie, Paris, France

    Bernard Silvi

  4. CNRS/UPM, MONARIS UMR 8233 (LADIR + LM2N), Paris, France

    Esmail Alikhani

Appendices

Behavior of Model Densities

See Fig. 18.19.

Fig. 18.19
figure 19

Behavior of s(ρ) for model densities ρ = e −αr for hydrogen and carbon

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Parameters for Promolecular Calculations

See Table 18.2.

Table 18.2 Parameterized exponents (η i ) and coefficients (c i ) of sphericalize averaged atomic densities, in atomic units
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Narth, C. et al. (2016). A Complete NCI Perspective: From New Bonds to Reactivity. In: Chauvin, R., Lepetit, C., Silvi, B., Alikhani, E. (eds) Applications of Topological Methods in Molecular Chemistry. Challenges and Advances in Computational Chemistry and Physics, vol 22. Springer, Cham. https://doi.org/10.1007/978-3-319-29022-5_18

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