Synthesis 2020; 52(04): 521-528
DOI: 10.1055/s-0039-1690209
paper
© Georg Thieme Verlag Stuttgart · New York

π-Hole Interactions with Various Nitro Compounds Relevant for Medicine: DFT Calculations and Surveys of the Cambridge Structural Database (CSD) and the Protein Data Bank (PDB)

Jari M. Hoffmann
,
Akshay K. Sadhoe
,
Tiddo J. Mooibroek  ∗
van’t Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands   eMail: t.j.mooibroek@uva.nl
› InstitutsangabenT.J.M. conducted the work with funds from the research program ‘VIDI­’ with project number 723.015.006, which is financed by the Nederlandse Organisatie voor Wetenschappelijk Onderzoek (Netherlands Organization for Scientific Research, NWO).
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Publikationsverlauf

Received: 22. August 2019

Accepted after revision: 16. September 2019

Publikationsdatum:
09. Oktober 2019 (online)

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Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

Model DFT computations and a thorough evaluation of the Cambridge structural database (CSD) and the protein data bank (PDB) were conducted to assess the occurrence and significance of intermolecular π-hole interactions with various nitro compounds relevant to medicine. DFT calculations indicate interaction energies between –3.9 to –6.5 kcal·mol–1, which is in the order of typical hydrogen- and halogen­-bonding interactions. Ample structural evidence for the occurrence of nitro π-hole interactions was found within the CSD and the PDB.

Key words

hydrogen bonding - halogen bonding - interaction energy - van der Waals overlap - crystal sructure - protein structure

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690209.
  • Supporting Information
 

  • References and Notes

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