Show simple item record

dc.contributor.authorTruong, Khai-Nghi
dc.contributor.authorRautiainen, J. Mikko
dc.contributor.authorRissanen, Kari
dc.contributor.authorPuttreddy, Rakesh
dc.date.accessioned2020-06-23T13:18:12Z
dc.date.available2020-06-23T13:18:12Z
dc.date.issued2020
dc.identifier.citationTruong, K.-N., Rautiainen, J. M., Rissanen, K., & Puttreddy, R. (2020). The C–I・・・⁻O–N⁺ Halogen Bonds with Tetraiodoethylene and Aromatic N-oxides. <i>Crystal Growth and Design</i>, <i>20</i>(8), 5330-5337. <a href="https://doi.org/10.1021/acs.cgd.0c00560" target="_blank">https://doi.org/10.1021/acs.cgd.0c00560</a>
dc.identifier.otherCONVID_36024523
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/70287
dc.description.abstractThe nature of C–I⋯⁻O–N⁺ interactions, first of its kind, between non-fluorinated tetraiodoethylene XB-donor and pyridine N-oxides (PyNO) are studied by single-crystal X-ray diffraction (SCXRD) and Density Functional Theory (DFT) calculations. Despite the non-fluorinated nature of the C2I4, the I⋯O halogen bond distances are similar to well-known perfluorohaloalkane/-arene donor-PyNO analogues. With C2I4, oxygens of the N-oxides adopt exclusively 2-XB-coordination in contrast to the versatile bonding modes observed with perfluorinated XB-donors. The C2I4 as the XB donor forms with PyNO’s one-dimensional chain polymer structures in which the C2I4⋯(μ-PyNO)2⋯C2I4 segments manifesting two bonding motifs, namely, side-by-side (vicinal di-iodo) and head-to-head (geminal di-iodo), due to the nearly symmetric square planar structure of the C2I4. While the attractive nature between I- and O-atoms is mainly electrostatic, the narrow range of C⋯O bond parameters demonstrate that the -bond between four iodine atoms also plays an important role in enhancing the -hole strength. DFT-based monodentate XB interaction energies, ΔEint, in thirteen 1:1 XB complexes vary between 31.9 – 46.5 kJ mol–1, the strongest remarkably exceeding the value reported for I–I⋯⁻O–N⁺ = 42.0 kJ mol–1. In case of C2I4・(pyridine N-oxide) [31.9 kJ mol–1], the monodentate XB energy is on a par with perfluorinated donor complexes, namely, CF3I・(pyridine N-oxide) [31.1 kJ mol–1] and C6F5I・(pyridine N-oxide) [32.3 kJ mol–1].en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesCrystal Growth and Design
dc.rightsIn Copyright
dc.subject.otherhalogeenisidokset
dc.subject.otherHalogen bond
dc.subject.otherN-oxide
dc.subject.otherpyridine
dc.subject.otherpyridine N-oxide
dc.subject.othertetraiodoethylene
dc.titleThe C–I・・・⁻O–N⁺ Halogen Bonds with Tetraiodoethylene and Aromatic N-oxides
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202006234479
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange5330-5337
dc.relation.issn1528-7483
dc.relation.numberinseries8
dc.relation.volume20
dc.type.versionacceptedVersion
dc.rights.copyright© 2020 American Chemical society
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber298817
dc.subject.ysokemialliset sidokset
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p10130
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi10.1021/acs.cgd.0c00560
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundinginformationThe research work is funded by Academy of Finland (RP: grant no. 298817), and Prof. H. M. Tuononen (University of Jyvaskyla) provided the computational resources. The authors gratefully acknowledge University of Jyvaskyla for providing laboratory and SCXRD resources.


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record

In Copyright
Except where otherwise noted, this item's license is described as In Copyright