5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

Crystals

MinoR. Caira¹  Denisa Dumitrescu²  Florea Dumitrascu³  IsabelaC. Man³  MarcelMirel Popa³  Sergiu Shova⁴ 

[1] Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;Faculty of Pharmacy, Ovidius University Constanta, Campus Corp C, Str. Cpt. Av. Al. Serbanescu, 900470 Constanta, Romania;“C.D. Nenitzescu” Center for Organic Chemistry, Romanian Academy, Spl. Independetei 202B, 060023 Bucharest, Romania;“Petru Poni” Institute for Macromolecular Chemistry, Department of Inorganic Polymers, Romanian Academy, Aleea Grigore Ghica Voda, 41A, 700487 Iasi, Romania;

关键词: halogen bond;    σ-hole;    5-iodo-pyrazole;    X-ray diffraction;    Hirshfeld analysis;   

DOI  :  10.3390/cryst10121149

来源: DOAJ

【 摘 要 】

5-Iodo-1-arylpyrazoles are interesting templates for investigating the halogen bond propensity in small molecules other than the already well-known halogenated molecules such as tetrafluorodiiodobenzene. Herein, we present six compounds with different substitution on the aryl ring attached at position 1 of the pyrazoles and investigate them in the solid state in order to elucidate the halogen bonding significance to the crystallographic landscape of such molecules. The substituents on the aryl ring are generally combinations of halogen atoms (Br, Cl) and various alkyl groups. Observed halogen bonding types spanned by these six 5-iodopyrazoles included a wide variety, namely, C–I⋯O, C–I⋯π, C–I⋯Br, C–I⋯N and C–Br⋯O interactions. By single crystal X-ray diffraction analysis combined with the descriptive Hirshfeld analysis, we discuss the role and influence of the halogen bonds among the intermolecular interactions.

【 授权许可】

Unknown