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)

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 indi...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2020-02, Vol.52 (4), p.521-528
Main Authors: Hoffmann, Jari M., Sadhoe, Akshay K., Mooibroek, Tiddo J.
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0039-1690209