Halogen interactions in halogenated oxindoles: Crystallographic and computational investigations of intermolecular interactions

Rodrigo A.Lemos Silva, Demetrio A. da Silva Filho, Megan E. Moberg, Ted M. Pappenfus, Daron E. Janzen

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2 Scopus citations

Abstract

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 (Eint (BSSE)) was determined using a supramolecular approach. The Eint (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.

Original languageEnglish (US)
Article number5487
JournalMolecules
Volume26
Issue number18
DOIs
StatePublished - Sep 2021

Bibliographical note

Funding Information:
Funding: D.E.J. and T.M.P. acknowledge funding for this project provided by the Minnesota Environment and Natural Resources Trust Fund as recommended by the Legislative-Citizen Commission on Minnesota Resources (LCCMR). D.E.J. acknowledges funding for this project provided by the Summer Scholars Undergraduate Research Program, St. Catherine University, and the National Science Foundation: Major Research Instrumentation award #1125975 “MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility”. D.A.d.S.F. acknowledges the financial support from the Edital DPI-UnB No. 02/2020, from CNPq (grants 305975/2019-6, 305975/2019-6, and 420836/2018-7) and FAP-DF (grants 193.001.596/2017 and 193.001.284/2016) R.A.L.S. acknowledges the financial support from CNPq (grant 164561/2017-0). D.E.J acknowledges partial funding of the APC by the Endowed Chair in the Sciences and Carondelet Scholars program, School of Humanities Arts and Sciences, St. Catherine University and partial funding by MDPI.

Funding Information:
D.E.J. and T.M.P. acknowledge funding for this project provided by the Minnesota Environment and Natural Resources Trust Fund as recommended by the Legislative-Citizen Commission on Minnesota Resources (LCCMR). D.E.J. acknowledges funding for this project provided by the Summer Scholars Undergraduate Research Program, St. Catherine University, and the National Science Foundation: Major Research Instrumentation award #1125975 ?MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility?. D.A.d.S.F. acknowledges the financial support from the Edital DPI-UnB No. 02/2020, from CNPq (grants 305975/2019-6, 305975/2019-6, and 420836/2018-7) and FAPDF (grants 193.001.596/2017 and 193.001.284/2016) R.A.L.S. acknowledges the financial support from CNPq (grant 164561/2017-0). D.E.J acknowledges partial funding of the APC by the Endowed Chair in the Sciences and Carondelet Scholars program, School of Humanities Arts and Sciences, St. Catherine University and partial funding by MDPI.

Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Halogen interactions
  • NBO
  • QTAIM
  • X-ray crystal structure

PubMed: MeSH publication types

  • Journal Article

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