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dc.contributor.authorAnyfanti, Goulielmina
dc.contributor.authorBauzá, Antonio
dc.contributor.authorGentiluomo, Lorenzo
dc.contributor.authorRodrigues, João
dc.contributor.authorPortalone, Gustavo
dc.contributor.authorFrontera, Antonio
dc.contributor.authorRissanen, Kari
dc.contributor.authorPuttreddy, Rakesh
dc.date.accessioned2021-05-04T06:26:38Z
dc.date.available2021-05-04T06:26:38Z
dc.date.issued2021
dc.identifier.citationAnyfanti, G., Bauzá, A., Gentiluomo, L., Rodrigues, J., Portalone, G., Frontera, A., Rissanen, K., & Puttreddy, R. (2021). Short X···N Halogen Bonds With Hexamethylenetetraamine as the Acceptor. <i>Frontiers in Chemistry</i>, <i>9</i>, Article 623595. <a href="https://doi.org/10.3389/fchem.2021.623595" target="_blank">https://doi.org/10.3389/fchem.2021.623595</a>
dc.identifier.otherCONVID_68159389
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/75287
dc.description.abstractHexamethylenetetramine (HMTA) and N-haloimides form two types of short (imide)X···N and X–X···N (X = Br, I) halogen bonds. Nucleophilic substitution or ligand-exchange reaction on the peripheral X of X–X···N with the chloride of N-chlorosuccinimide lead to Cl–X···N halogen-bonded complexes. The 1:1 complexation of HMTA and ICl manifests the shortest I···N halogen bond [2.272(5) Å] yet reported for an HMTA acceptor. Two halogen-bonded organic frameworks are prepared using 1:4 molar ratio of HMTA and N-bromosuccinimide, each with a distinct channel shape, one possessing oval and the other square grid. The variations in channel shapes are due to tridentate and tetradentate (imide)Br···N coordination modes of HMTA. Density Functional Theory (DFT) studies are performed to gain insights into (imide)X···N interaction strengths (ΔEint). The calculated ΔEint values for (imide)Br···N (−11.2 to −12.5 kcal/mol) are smaller than the values for (imide)I···N (−8.4 to −29.0 kcal/mol). The DFT additivity analysis of (imide)Br···N motifs demonstrates Br···N interaction strength gradually decreasing from 1:1 to 1:3 HMTA:N-bromosuccinimide complexes. Exceptionally similar charge density values ρ(r) for N–I covalent bond and I···N non-covalent bond of a (saccharin)N–I···N motif signify the covalent character for I···N halogen bonding.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherFrontiers Media SA
dc.relation.ispartofseriesFrontiers in Chemistry
dc.rightsCC BY 4.0
dc.subject.otherhalogen bond
dc.subject.otherhexamethylenetetraamine
dc.subject.otherHMTA
dc.subject.otherN-haloimide
dc.subject.otherdihalogen
dc.subject.otherinterhalogen
dc.titleShort X···N Halogen Bonds With Hexamethylenetetraamine as the Acceptor
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202105042601
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.relation.issn2296-2646
dc.relation.volume9
dc.type.versionpublishedVersion
dc.rights.copyright© 2021 the Authors
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber298817
dc.subject.ysohalogeenit
dc.subject.ysoorgaaniset yhdisteet
dc.subject.ysosupramolekulaarinen kemia
dc.subject.ysokemialliset sidokset
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p4164
jyx.subject.urihttp://www.yso.fi/onto/yso/p3841
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
jyx.subject.urihttp://www.yso.fi/onto/yso/p10130
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3389/fchem.2021.623595
dc.relation.funderResearch Council of Finlanden
dc.relation.funderSuomen Akatemiafi
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundinginformationThe authors gratefully acknowledge financial support from the Academy of Finland (RP: grant no. 298817) and the University of Jyväskylä. AF and AB thank the MICIU/AEI from Spain for financial support (project number CTQ2017-85821-R, FEDER funds). JR acknowledges the support of FCT-Fundação para a Ciência e a Tecnologia (Base Fund UIDB/00674/2020 and Programmatic Fund UIDP/00674/2020, Portuguese Government Funds).
dc.type.okmA1


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