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Synthesis 2020; 52(04): 521-528
DOI: 10.1055/s-0039-1690209
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)
T.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).Further Information
Publication History
Received: 22 August 2019
Accepted after revision: 16 September 2019
Publication Date:
09 October 2019 (online)
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 structureSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690209.
- Supporting Information
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