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Open AccessFeature PaperArticle

Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design

1
Department of Nanopharmaceutical Sciences, and Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
2
Research Center for Computational Design of Advanced Functional Materials, AIST, Tsukuba, Ibaraki 305-8568, Japan
3
Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, Jinhua 321004, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2019, 24(19), 3610; https://doi.org/10.3390/molecules24193610
Received: 24 August 2019 / Revised: 26 September 2019 / Accepted: 3 October 2019 / Published: 7 October 2019
(This article belongs to the Special Issue Fabulous Fluorine in Organic and Medicinal Chemistry)
The activation of halogen bonding by the substitution of the pentafluoro-λ6-sulfanyl (SF5) group was studied using a series of SF5-substituted iodobenzenes. The simulated electrostatic potential values of SF5-substituted iodobenzenes, the ab initio molecular orbital calculations of intermolecular interactions of SF5-substituted iodobenzenes with pyridine, and the 13C-NMR titration experiments of SF5-substituted iodobenzenes in the presence of pyridine or tetra (n-butyl) ammonium chloride (TBAC) indicated the obvious activation of halogen bonding, although this was highly dependent on the position of SF5-substitution on the benzene ring. It was found that 3,5-bis-SF5-iodobenzene was the most effective halogen bond donor, followed by o-SF5-substituted iodobenzene, while the m- and p-SF5 substitutions did not activate the halogen bonding of iodobenzenes. The similar ortho-effect was also confirmed by studies using a series of nitro (NO2)-substituted iodobenzenes. These observations are in good agreement with the corresponding Mulliken charge of iodine. The 2:1 halogen bonding complex of 3,5-bis-SF5-iodobenzene and 1,4-diazabicyclo[2.2.2]octane (DABCO) was also confirmed. Since SF5-containing compounds have emerged as promising novel pharmaceutical and agrochemical candidates, the 3,5-bis-SF5-iodobenzene unit may be an attractive fragment of rational drug design capable of halogen bonding with biomolecules. View Full-Text
Keywords: halogen bonding; fluorine; iodine; pentafluorosulfanyl; titration; ab initio calculation; NMR study; drug design halogen bonding; fluorine; iodine; pentafluorosulfanyl; titration; ab initio calculation; NMR study; drug design
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MDPI and ACS Style

Sumii, Y.; Sasaki, K.; Tsuzuki, S.; Shibata, N. Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design. Molecules 2019, 24, 3610.

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