A1 Journal article (refereed)
Halogen Bonding in Halothiophene Building Blocks (2023)


Koivuporras, A., Mailman, A., Guo, H., Priimagi, A., & Puttreddy, R. (2023). Halogen Bonding in Halothiophene Building Blocks. Crystal Growth and Design, 23(12), 8889-8896. https://doi.org/10.1021/acs.cgd.3c00958


JYU authors or editors


Publication details

All authors or editorsKoivuporras, Alisa; Mailman, Aaron; Guo, Hongshuang; Priimagi, Arri; Puttreddy, Rakesh

Journal or seriesCrystal Growth and Design

ISSN1528-7483

eISSN1528-7505

Publication year2023

Publication date15/11/2023

Volume23

Issue number12

Pages range8889-8896

PublisherAmerican Chemical Society

Publication countryUnited States

Publication languageEnglish

DOIhttps://doi.org/10.1021/acs.cgd.3c00958

Publication open accessOpenly available

Publication channel open accessPartially open access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/91958


Abstract

Thiophenes bearing monotopic and symmetric ditopic halogen substituents and asymmetric ditopic halogen and pyridine substituents that act as halogen bond acceptors were evaluated for their halogen bonding interactions with 1,4-diiodotetrafluorobenzene and N-iodosuccinimide. The combinations resulted in C/N–I···X′ (X′ = Cl, Br, I) and C/N–I···NPy (Py = pyridine) interactions, the former characterized by an interaction energy (ΔEint) ranging from −4.4 to −18.7 kJ mol–1 and the latter from −26.3 to −56.0 kJ mol–1. X-ray crystallography studies show that the ditopic asymmetric systems consisting of both halogens and pyridine self-associate through C–X···NPy (X = Cl, Br, I) halogen bonding, and in their optimized structures the energies range from −5.4 to −19.6 kJ mol–1 depending on the type of halogen atom present. The 1H NMR association constants of N–I···NPy halogen bonds range between 1405 and 6397 M–1. The σ-hole strengths of halogens have been useful in describing the interaction energies and solution models.


Keywordsnitrogenhalogens

Free keywordsmolecular interactions; nitrogen; noncovalent interactions; thiophenes


Contributing organizations


Ministry reportingYes

VIRTA submission year2023

JUFO rating2


Last updated on 2024-12-10 at 18:16