Halogen-Bonded Mono-, Di-, and Tritopic N-Alkyl-3-iodopyridinium Salts
Year of publication
2023
Authors
Rautiainen, J. Mikko; Green, Maryna; Mahonen, Minna; Moilanen, Jani O.; Lahtinen, Manu; Valkonen, Arto
Abstract
Halogen bonding interactions of 15 crystalline 3-iodopyridinium systems were investigated. These systems were derived from four N-alkylated 3-iodopyridinium salts prepared in this study. The experimental results in the solid state show that halogen bonding acts as a secondary intermolecular force in these charged systems but sustains the high directionality of interaction in the presence of other intermolecular forces. Halogen bonds donated by polytopic 3-iodopyridinium cations are also sufficient to enclose guest molecules inside the formed supramolecular cavities. The experimental data were supplemented by computational gas-phase and solid-state studies for selected halogen-bonded systems. Calculations of the model systems with the increasing number of halogen bond donors and acceptors showed the halogen bond strengths to be exaggerated for the smallest of model systems. The agreement between experimental and calculated structures improved for larger systems that were able to account for the influence of other intermolecular interactions. The best agreement between experimental and calculated structural parameters were found for solid-state calculations with periodic boundary conditions. Comparison of the halogen bond interaction strengths with the strength of other lattice interactions showed the halogen bonds to come second to electrostatic interactions in stabilizing the structures but having a major role in directing the packing of the solid-state structures.
Show moreOrganizations and authors
University of Helsinki
Green Maryna
Publication type
Publication format
Article
Parent publication type
Journal
Article type
Original article
Audience
ScientificPeer-reviewed
Peer-ReviewedMINEDU's publication type classification code
A1 Journal article (refereed), original researchPublication channel information
Journal
Parent publication name
Publisher
Volume
23
Issue
4
Pages
2361-2374
ISSN
Publication forum
Publication forum level
2
Open access
Open access in the publisher’s service
Yes
Open access of publication channel
Partially open publication channel
Self-archived
Yes
Other information
Fields of science
Chemical sciences; Biochemistry, cell and molecular biology
Keywords
[object Object],[object Object],[object Object],[object Object]
Publication country
United States
Internationality of the publisher
International
Language
English
International co-publication
No
Co-publication with a company
No
DOI
10.1021/acs.cgd.2c01351
The publication is included in the Ministry of Education and Culture’s Publication data collection
Yes