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 editors: Koivuporras, Alisa; Mailman, Aaron; Guo, Hongshuang; Priimagi, Arri; Puttreddy, Rakesh
Journal or series: Crystal Growth and Design
ISSN: 1528-7483
eISSN: 1528-7505
Publication year: 2023
Publication date: 15/11/2023
Volume: 23
Issue number: 12
Pages range: 8889-8896
Publisher: American Chemical Society
Publication country: United States
Publication language: English
DOI: https://doi.org/10.1021/acs.cgd.3c00958
Publication open access: Openly available
Publication channel open access: Partially 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.
Free keywords: molecular interactions; nitrogen; noncovalent interactions; thiophenes
Contributing organizations
Ministry reporting: Yes
VIRTA submission year: 2023
JUFO rating: 2
- Inorganic Chemistry (Department of Chemistry CHEM)
- Nanoscience Center (Department of Physics PHYS, JYFL) (Faculty of Mathematics and Science) (Department of Chemistry CHEM) (Department of Biological and Environmental Science BIOENV) NSC
- The Unit of Applied Chemistry (Kokkola University Consortium Chydenius KYC, CHYD)
- Organic Chemistry (Department of Chemistry CHEM) KEO