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Small cycloalkane 1,1',2,2'-tetracyano structures are highly directional non-covalent carbon-bond donors

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dc.contributor.author Bauzá Riera, Antonio
dc.contributor.author Mooibroek, Tiddo J.
dc.contributor.author Frontera Beccaria, Antonio
dc.date.accessioned 2018-10-04T10:28:06Z
dc.identifier.uri http://hdl.handle.net/11201/147917
dc.description.abstract [eng] High-level calculations (RI-MP2/def2-TZVP) disclosed that the s-hole in between two C atoms of cycloalkane X2C CX2 structures (X=F, CN) is increasingly exposed with decreasing ring size. The interacting energy of complexes of F , HO , N C , and H2CO with cyclopropane and cyclobutane X2C CX2 derivatives was calculated. For X=F, these energies are small to positive, while for X=CN they are all negative, ranging from 6.8 to 42.3 kcal mol 1. These finding are corroborated by a thorough statistical survey of the Cambridge Structural Database (CSD). No clear evidence could be found in support of non-covalent carbon bonding between electron-rich atoms (El.R.) and F2C CF2 structures. In marked contrast, El.R.···(CN)2C C(CN)2 interactions are abundant and highly directional. Based on these findings, the hydrophobic electrophilic bowl formed by 1,1',2,2'-tetracyano cyclopropane or cyclobutane derivatives is proposed as a new and synthetically accessible supramolecular synthon.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1002/chem.201403680
dc.relation.ispartof Chemistry-A European Journal, 2014, vol. 20, p. 10245-10248
dc.rights (c) Wiley-VHC Verlag GmbH & Co., 2014
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Small cycloalkane 1,1',2,2'-tetracyano structures are highly directional non-covalent carbon-bond donors
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-04T10:28:06Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1002/chem.201403680


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