Halogen Bonding Involving Isomeric Isocyanide/Nitrile Groups DOI Open Access

Andrey S. Smirnov,

Eugene A. Katlenok, Alexander S. Mikherdov

et al.

Published: July 28, 2023

2,3,5,6-Tetramethyl-1,4-diisocyanobenzene (1), 1,4-diisocyanobenzene (2), and 1,4-dicyanobenzene (3) were co-crystallized with 1,3,5-triiodotrifluorobenzene (1,3,5-FIB) to give three cocrystals, 1·1,3,5-FIB, 2·2(1,3,5-FIB), 3·2(1,3,5-FIB), which studied by XRD. Common feature of the structures is presence I···Cisocyanide or I···Nnitrile HaBs occurred between an iodine -hole isocyanide C- (or nitrile N-) atom. The diisocyanide dinitrile 2·2(1,3,5-FIB) are isostructural thus providing a basis for accurate comparison two types noncovalent linkages CN/NC groups in composition structurally similar entities one crystal environment. bonding situation was set theoretical methods. Diisocyanides more nucleophilic than they exhibit stronger binding 1,3,5-FIB. In all structures, mostly determined electrostatic interactions, but dispersion induction components also provide noticeable contribution make attractive. Charge transfer has small (<5%) HaB it higher systems. At same time, typical electron-donor -acceptor properties relation donor.

Language: Английский

Halogen Bonding Involving Isomeric Isocyanide/Nitrile Groups DOI Open Access

Andrey S. Smirnov,

Eugene A. Katlenok, Alexander S. Mikherdov

et al.

Published: July 28, 2023

2,3,5,6-Tetramethyl-1,4-diisocyanobenzene (1), 1,4-diisocyanobenzene (2), and 1,4-dicyanobenzene (3) were co-crystallized with 1,3,5-triiodotrifluorobenzene (1,3,5-FIB) to give three cocrystals, 1·1,3,5-FIB, 2·2(1,3,5-FIB), 3·2(1,3,5-FIB), which studied by XRD. Common feature of the structures is presence I···Cisocyanide or I···Nnitrile HaBs occurred between an iodine -hole isocyanide C- (or nitrile N-) atom. The diisocyanide dinitrile 2·2(1,3,5-FIB) are isostructural thus providing a basis for accurate comparison two types noncovalent linkages CN/NC groups in composition structurally similar entities one crystal environment. bonding situation was set theoretical methods. Diisocyanides more nucleophilic than they exhibit stronger binding 1,3,5-FIB. In all structures, mostly determined electrostatic interactions, but dispersion induction components also provide noticeable contribution make attractive. Charge transfer has small (<5%) HaB it higher systems. At same time, typical electron-donor -acceptor properties relation donor.

Language: Английский

Citations

1