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RESEARCH PRODUCT

Influence of Substituents in the Aromatic Ring on the Strength of Halogen Bonding in Iodobenzene Derivatives

Matti HaukkaMaria V. ChernyshevaMargarita BulatovaXin Ding

subject

Halogen bond010405 organic chemistryIodobenzeneSubstituentGeneral ChemistryMesomeric effect010402 general chemistryCondensed Matter PhysicsRing (chemistry)01 natural sciencesMedicinal chemistryHexaiodobenzene0104 chemical scienceschemistry.chemical_compoundchemistryHalogenGeneral Materials Science

description

Halogen bonding properties of 3,4,5-triiodobenzoic acid (1, 2), 1,2,3-triiodobenzene (3), pentaiodobenzoic acid ethanol solvate (4), hexaiodobenzene (5a, 5b, 5c), 2,4-diiodoaniline (6), 4-iodoaniline (7), 2-iodoaniline (8), 2-iodophenol (9), 4-iodophenol (10), 3-iodophenol (11) and 2,4,6-triiodophenol (12) has been studied. The results suggested that substituents other than halogen in aromatic ring affect XB properties of iodine substituents in ortho-, meta- and para-positions. The effect depends on the electron-withdrawing/electron-donating properties of the substituent. Thus, electron-withdrawing substituents with negative mesomeric effect favor m-iodines to act as XB donors and o- and p-iodines to act as XB acceptors. By contrast, electron substituents with positive mesomeric effect favor o- and p-iodines to act as XB donors and m-iodines to act as XB acceptors.

yearjournalcountryeditionlanguage
2020-09-17Crystal Growth & Design
https://doi.org/10.1021/acs.cgd.0c00866