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Theoretical description of halogen bonding : an insight based on the natural orbitals for chemical valence combined with the extended-transition-state method (ETS-NOCV)

Theoretical description of halogen bonding : an ...

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dc.contributor.author Mitoraj, Mariusz [SAP11019444] pl
dc.contributor.author Michalak, Artur [SAP11015048] pl
dc.date.accessioned 2015-06-23T11:49:10Z
dc.date.available 2015-06-23T11:49:10Z
dc.date.issued 2013 pl
dc.identifier.issn 1610-2940 pl
dc.identifier.uri http://ruj.uj.edu.pl/xmlui/handle/item/10118
dc.language eng pl
dc.rights Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa *
dc.rights.uri http://creativecommons.org/licenses/by/4.0/pl/legalcode *
dc.title Theoretical description of halogen bonding : an insight based on the natural orbitals for chemical valence combined with the extended-transition-state method (ETS-NOCV) pl
dc.type JournalArticle pl
dc.description.physical 4681-4688 pl
dc.identifier.weblink https://link.springer.com/content/pdf/10.1007%2Fs00894-012-1474-4.pdf pl
dc.abstract.en In the present study we have characterized the halogen bonding in selected molecules H 3 N – ICF 3 ( 1- NH 3 ), (PH 3 ) 2 C – ICF 3 ( 1-CPH 3 ), C 3 H 7 Br – (IN 2 H 2 C 3 ) 2 C 6 H 4 ( 2-Br ), H 2 – (IN 2 H 2 C 3 ) 2 C 6 H 4 ( 2-H 2 ) and Cl – (IC 6 F 5 ) 2 C 7 H 10 N 2 O 5 ( 3-Cl) , containing from one halogen bond ( 1-NH 3 , 1-CPH 3 ) up to four connections in 3-Cl (the two Cl – HN and two Cl – I), based on recently proposed ETS- NOCV analysis. It was found based on the NOCV- deformation density components that the halogen bonding C – X ... B (X-halogen atom, B-Lewis base), contains a large degree of covalent contribution (the charge transfer to X ... B inter-atomic region) supported further by the electron dona- tion from base atom B to the empty σ *(C – X) orbital. Such charge transfers can be of similar importance compared to the electrostatic stabilization. Further, the covalent part of halogen bonding is due to the presence of σ -hole at outer part of halogen atom (X). ETS-NOCV approach allowed to visualize formation of the σ -hole at iodine atom of CF 3 I molecule. It has also been demonstrated that strongly elec- trophilic halogen bond donor, [C 6 H 4 (C 3 H 2 N 2 I) 2 ][OTf] 2 , can activate chemically inert isopropyl bromide ( 2-Br ) moiety via formation of Br – I bonding and bind the hydrogen mol- ecule ( 2-H 2 ). Finally, ETS-NOCVanalysis performed for 3- Cl leads to the conclusion that, in terms of the orbital- interaction component, the strength of halogen (Cl – I) bond is roughly three times more important than the hydrogen bonding (Cl – HN). pl
dc.description.volume 19 pl
dc.description.number 11 pl
dc.identifier.doi 10.1007/s00894-012-1474-4 pl
dc.identifier.eissn 0948-5023 pl
dc.title.journal Journal of Molecular Modeling pl
dc.language.container eng pl
dc.date.accession 2018-07-12 pl
dc.affiliation Wydział Chemii : Zakład Chemii Teoretycznej im. K. Gumińskiego pl
dc.affiliation Wydział Chemii : Zakład Metod Obliczeniowych Chemii pl
dc.subtype Article pl
dc.rights.original CC-BY; inne; ostateczna wersja wydawcy; w momencie opublikowania; 0 pl
dc.identifier.project ROD UJ / P pl
.pointsMNiSW [2013 A]: 25


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Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa Except where otherwise noted, this item's license is described as Udzielam licencji. Uznanie autorstwa 4.0 Międzynarodowa