A1 Journal article (refereed)
Influence of substituents in aromatic ring on the strength of halogen bonding in iodobenzene derivatives (2020)


Chernysheva, Maria V.; Bulatova, Margarita; Ding, Xin; Haukka, Matti (2020). Influence of substituents in aromatic ring on the strength of halogen bonding in iodobenzene derivatives. Crystal Growth and Design, 20 (11), 7197-7210. DOI: 10.1021/acs.cgd.0c00866


JYU authors or editors


Publication details

All authors or editors: Chernysheva, Maria V.; Bulatova, Margarita; Ding, Xin; Haukka, Matti

Journal or series: Crystal Growth and Design

ISSN: 1528-7483

eISSN: 1528-7505

Publication year: 2020

Volume: 20

Issue number: 11

Pages range: 7197-7210

Publisher: American Chemical Society (ACS)

Publication country: United States

Publication language: English

DOI: http://doi.org/10.1021/acs.cgd.0c00866

Open Access: Publication channel is not openly available

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/71843


Abstract

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.


Keywords: halogens; chemical bonds


Contributing organizations


Ministry reporting: Yes

Preliminary JUFO rating: 2


Last updated on 2020-09-11 at 15:57