Abstract
The crystal structure of the newly synthesized 4-methoxyphenyl(phenyl)iodonium thiocyanate, [PhI(4-C6H4OMe)](SCN), represents the first example of 16-membered cyclic heterooctamer formed by halogen bonding between the iodonium cation and SCN−. Results of density functional theory (DFT) calculations followed by the topological analysis of the electron density distribution within the framework of the quantum theory of atoms in molecules (QTAIM) method at the ωB97XD/DZP-DKH level of theory reveal that energies of attractive intermolecular noncovalent interactions I···S and I···N (responsible for the formation of heterooctameric supramolecular clusters {PhI(4-C6H4OMe)}4·{SCN}4 in the solid state structure of [PhI(4-C6H4OMe)](SCN)) vary from 0.9 to 8.5 kcal/mol.
Highlights
Halogen bonding (XB) has drawn increased attention in the past decade as a powerful tool for crystal engineering and supramolecular chemistry [1,2,3,4,5], drug design [6,7,8], organic synthesis [9,10,11], and as a route for facile tuning of physicochemical properties [12,13]
Upon our processing of CCDC, we found two more structures of diaryliodonium thiocyanates such
I1···N1A distances are closer to the relevant values observed in polymeric 2, rather than those in 3; High-resolution electrospray ionization (HRESI) mass-spectra were obtained on a Bruker maXis we assume that this is probably because of the electron withdrawing effect of C6F5 in 3
Summary
Halogen bonding (XB) has drawn increased attention in the past decade as a powerful tool for crystal engineering and supramolecular chemistry [1,2,3,4,5], drug design [6,7,8], organic synthesis [9,10,11], and as a route for facile tuning of physicochemical properties [12,13]. Bock and Hall [18,19,20] have identified XB between SCN− and iodine centers in tetraiodoethylene or tetraiodothiophene; SCN− in Crystals 2020, 10, 230; doi:10.3390/cryst10030230 www.mdpi.com/journal/crystals dropwise to a solution of KSCN (5 mmol, 485 mg) in water (1 mL) at RT, whereupon the reaction mixture was stirred for 30 min, the precipitate formed was filtered off and washed with water
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
