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

doi:10.1055/s-0039-1690209

Synthesis, Table of Contents

Synthesis 2020; 52(04): 521-528
DOI: 10.1055/s-0039-1690209

paper

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

› Author Affiliations

Abstract

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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

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References

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