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1. Halogen Bonding Provides Heterooctameric Supramolecular Aggregation of Diaryliodonium Thiocyanate

Author

Natalia S. Soldatova, Vitalii V. Suslonov, Troyana Yu. Kissler, Daniil M. Ivanov, Alexander S. Novikov, Mekhman S. Yusubov, Pavel S. Postnikov, and Vadim Yu. Kukushkin

Subjects
halogen bonding, noncovalent interactions, dft, qtaim, hypervalent iodine, diaryliodonium salts, thiocyanate, Crystallography, QD901-999
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.

Published
2020
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2. Diaryliodonium as a double σ-hole donor: the dichotomy of thiocyanate halogen bonding provides divergent solid state arylation by diaryliodonium cations

Author

Pavel S. Postnikov, Vitalii V. Suslonov, Troyana Yu. Kissler, Vadim Yu. Kukushkin, Natalia S. Soldatova, Mekhman S. Yusubov, Antonio Frontera, Daniil M. Ivanov, and Bartomeu Galmés

Subjects
chemistry.chemical_classification, Crystallography, chemistry.chemical_compound, Halogen bond, Thiocyanate, Chemistry, Organic Chemistry, Atoms in molecules, Supramolecular chemistry, Solid-state, Non-covalent interactions, Density functional theory, Chemoselectivity
Abstract

X-ray crystallography data revealed the dichotomy of thiocyanate-involving noncovalent interactions in [Ar1Ar2I](SCN), as reflected in the generation of two types of supramolecular aggregates: (i) previously unreported 4-membered heterotetramers (Ar1/Ar2 = 4-ClC6H4/2,4,6-(MeO)3C6H2, 4-BrC6H4/2,4,6-(MeO)3C6H2; 2 examples) featuring exclusively halogen bond (XB) N-XB-bound SCN− anions, and (ii) the 8-membered cyclic heterotetramers (Ar1/Ar2 = Ph/Ph, Ph/2,4,6-(MeO)3C6H2, 4-FC6H4/2,4,6-(MeO)3C6H2, 3,5-Me2C6H3/4-MeOC6H4, 3,5-Me2C6H3/2,4,6-(MeO)3C6H2; 5 examples) with two N,S-XB-bound thiocyanates featuring both S⋯I and N⋯I noncovalent contacts. In all cases, the IIII centers function as a double σ-hole donor to provide two directional XBs. The XB preorganization affects the chemoselectivity of the thiocyanate arylation in the solid-state: the heating of [Ar1Ar2I](SCN) exhibiting either N-, or N,S preorganized XBs leads to extremely rare N-arylation or the conventional S-arylation, respectively. The charge-assisted XBs in [Ar1Ar2I](SCN) were studied using density functional theory (DFT) calculations combined with a molecular electrostatic potential surface analysis and the quantum theory of atoms in molecules (QTAIM). Competition between the N- and N,S-XB interactions was studied, including the recognition of energy differences between the I⋯N and I⋯S contacts. The computational data were useful to rationalize the divergent solid-state N- or S-arylation of thiocyanates.

Published
2020

3. Halogen Bonding Provides Heterooctameric Supramolecular Aggregation of Diaryliodonium Thiocyanate

Author

Pavel S. Postnikov, Troyana Yu. Kissler, Mekhman S. Yusubov, Daniil M. Ivanov, Vitalii V. Suslonov, Vadim Yu. Kukushkin, Natalia S. Soldatova, and Alexander S. Novikov

Subjects
qtaim, General Chemical Engineering, Supramolecular chemistry, Crystal structure, 010402 general chemistry, 01 natural sciences, Inorganic Chemistry, noncovalent interactions, chemistry.chemical_compound, lcsh:QD901-999, Non-covalent interactions, General Materials Science, chemistry.chemical_classification, thiocyanate, Halogen bond, Thiocyanate, 010405 organic chemistry, Chemistry, halogen bonding, noncovalent interactions, DFT, QTAIM, hypervalent iodine, diaryliodonium salts, thiocyanate, Intermolecular force, Atoms in molecules, dft, Condensed Matter Physics, 0104 chemical sciences, Crystallography, hypervalent iodine, halogen bonding, diaryliodonium salts, Density functional theory, lcsh:Crystallography
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&ndash, 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 &omega, B97XD/DZP-DKH level of theory reveal that energies of attractive intermolecular noncovalent interactions I&middot, &middot, S and I&middot, N (responsible for the formation of heterooctameric supramolecular clusters {PhI(4-C6H4OMe)}4&middot, {SCN}4 in the solid state structure of [PhI(4-C6H4OMe)](SCN)) vary from 0.9 to 8.5 kcal/mol.

Published
2020

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