On the importance of halogen bonding interactions in two X-ray structures containing all four (F, Cl, Br, I) halogen atoms

This manuscript reports the synthesis and X-ray characterization of two octahydro-1H-4,6-epoxycyclopenta[c]pyridin-1-one derivatives that contain the four most abundant halogen atoms (Ha) in the structure with the aim of studying the formation of Ha···Ha halogen bonding interactions. The anisotropy of electron density at the heavier halogen atoms provokes the formation of multiple Ha···Ha contacts in the solid state. That is, the heavier Ha-atoms exhibit a region of positive electrostatic potential (σ-hole) along the C–Ha bond and a belt of negative electrostatic potential (σ-lumps) around the atoms. The halogen bonding assemblies in both compounds were analyzed using density functional theory (DFT) calculations, molecular electrostatic potential (MEP) surfaces, the quantum theory of “atom-in-molecules” (QTAIM), the noncovalent interaction plot (NCIplot), and the electron localization function (ELF). © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Authors
Mertsalov D.F. 1 , Gomila R.M.2 , Zaytsev V.P. 1 , Grigoriev M.S.3 , Nikitina E.V. 1 , Zubkov F.I. 1 , Frontera A.2
Journal
Publisher
MDPI AG
Number of issue
11
Language
English
Status
Published
Number
1406
Volume
11
Year
2021
Organizations
  • 1 Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 2 Department of Chemistry, Universitat de les Illes Balears, Crta. de Valldemossa km 7.5, Palma, 07122, Spain
  • 3 Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31/4 Leninskiy prosp, Moscow, 119071, Russian Federation
Keywords
Crystal engineering; Halogen bonding; Supramolecular chemistry; σ-hole
Date of creation
16.12.2021
Date of change
16.12.2021
Short link
https://repository.rudn.ru/en/records/article/record/76507/
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