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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.
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Organizations and authors

University of Jyväskylä

Valkonen Arto Orcid -palvelun logo

Moilanen Jani

Lahtinen Manu Orcid -palvelun logo

Rautiainen Mikko Orcid -palvelun logo

Publication type

Publication format

Article

Parent publication type

Journal

Article type

Original article

Audience

Scientific

Peer-reviewed

Peer-Reviewed

MINEDU's publication type classification code

A1 Journal article (refereed), original research

Publication channel information

Parent publication name

Crystal Growth & Design

Volume

23

Issue

4

Pages

2361-2374

​Publication forum

54281

​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

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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