Halogen-Bonded Mono-, Di-, and Tritopic N-Alkyl-3-iodopyridinium Salts
Rautiainen, J. M., Green, M., Mähönen, M., Moilanen, J. O., Lahtinen, M., & Valkonen, A. (2023). Halogen-Bonded Mono-, Di-, and Tritopic N-Alkyl-3-iodopyridinium Salts. Crystal Growth and Design, 23(4), 2361-2374. https://doi.org/10.1021/acs.cgd.2c01351
Published inCrystal Growth and Design
DisciplineEpäorgaaninen kemiaResurssiviisausyhteisöNanoscience CenterOrgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaInorganic ChemistrySchool of Resource WisdomNanoscience CenterOrganic ChemistryInorganic and Analytical Chemistry
© The Authors. Published by American Chemical Society
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. ...
PublisherAmerican Chemical Society (ACS)
ISSN Search the Publication Forum1528-7483
Publication in research information system
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Related funder(s)Academy of Finland
Funding program(s)Research costs of Academy Research Fellow, AoF; Academy Research Fellow, AoF
Additional information about fundingThe Academy of Finland (A.V., Grant nos. 314343 and 335600 and J.O.M., Grant nos. 315829, 320015, and 345484) and the University of Jyväskylä are gratefully acknowledged for financial support. The authors thank Spec. Lab. Tech. Mirja Lahtiperä and Dr. Elina Kalenius for their work with mass spectrometry. We are also grateful to Prof. Kari Rissanen for his support and suggestions for the research. The CSC-IT Centre for Science in Finland, the Finnish Grid and Cloud Infrastructure (persistent identifier urn:nbn:fi:research-infras-2016072533) and Prof. H. M. Tuononen (University of Jyväskylä) are acknowledged for providing computational resources for the project. ...
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