Halogen Interactions in Halogenated Oxindoles: Crystallographic and Computational Investigations of Intermolecular Interactions.

Autor: Silva RAL; Institute of Physics, University of Brasilia, Brasilia 70910-900, Brazil., da Silva Filho DA; Institute of Physics, University of Brasilia, Brasilia 70910-900, Brazil.; International Center for Condensed Matter Physics, University of Brasilia, CP 04455, Brasilia 70919-970, Brazil., Moberg ME; Department of Chemistry & Biochemistry, St. Catherine University, St. Paul, MN 55105, USA., Pappenfus TM; Division of Science and Mathematics, University of Minnesota, Morris, MN 56267, USA., Janzen DE; Department of Chemistry & Biochemistry, St. Catherine University, St. Paul, MN 55105, USA.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2021 Sep 09; Vol. 26 (18). Date of Electronic Publication: 2021 Sep 09.
DOI: 10.3390/molecules26185487
Abstrakt: X-ray structural determinations and computational studies were used to investigate halogen interactions in two halogenated oxindoles. Comparative analyses of the interaction energy and the interaction properties were carried out for Br···Br, C-H···Br, C-H···O and N-H···O interactions. Employing Møller-Plesset second-order perturbation theory (MP2) and density functional theory (DFT), the basis set superposition error (BSSE) corrected interaction energy (E int (BSSE)) was determined using a supramolecular approach. The E int (BSSE) results were compared with interaction energies obtained by Quantum Theory of Atoms in Molecules (QTAIM)-based methods. Reduced Density Gradient (RDG), QTAIM and Natural bond orbital (NBO) calculations provided insight into possible pathways for the intermolecular interactions examined. Comparative analysis employing the electron density at the bond critical points (BCP) and molecular electrostatic potential (MEP) showed that the interaction energies and the relative orientations of the monomers in the dimers may in part be understood in light of charge redistribution in these two compounds.
Databáze: MEDLINE
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