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dc.date.accessioned2018-01-31T13:54:53Z
dc.date.available2018-01-31T13:54:53Z
dc.date.issued2017-07-07
dc.identifier.issn1420-3049
dc.identifier.uriurn:nbn:de:hebis:34-2018013154265
dc.identifier.urihttp://hdl.handle.net/123456789/2018013154265
dc.description.sponsorshipGefördert durch den Publikationsfonds der Universität Kassel
dc.language.isoeng
dc.subjectconjugated mesomeric betaineeng
dc.subjectcoinage metalseng
dc.subjectcoppereng
dc.subjectcrystal structureeng
dc.subjectgoldeng
dc.subjectN-heterocyclic carbeneeng
dc.subjectsilvereng
dc.subject1,2,4-triazol-5-ylideneeng
dc.subject.ddc500
dc.titleCoinage Metal Complexes of the Carbenic Tautomer of a Conjugated Mesomeric Betaine Akin to Nitroneng
dc.typeAufsatz
dcterms.abstractThis study was motivated by our recent observation that the analytical reagent Nitron (2) is an “instant carbene”, whose reaction with coinage metal salts MX afforded complexes of its carbenic tautomer 1,4-diphenyl-3-phenylamino-1,2,4-triazol-5-ylidene (2′). Our aim was to establish an alkyl homologue of 2 in order to achieve a carbenic tautomer of higher donicity. For this purpose 1-tert-butyl-4-methyl-1,2,4-triazol-4-ium-3-tert-butylaminide (6) was synthesized. Its reactions with MX afforded complexes of the carbenic tautomer 1-tert-butyl-3-tert-butylamino-4-methyl-1,2,4-triazol-5-ylidene (6′). With a stoichiometric ratio of 1:1 complexes of the type [MX(6′)] were obtained. A ratio of 2:1 furnished complexes of the type [MX(6′)2] or [M(6′)2]X. 6′ is a better σ-donor and less electrophilic than 2′ according to NMR spectroscopic data of 6H[BF4] and 6′ = Se, respectively, and IR spectroscopic data of [RhCl(6′)(CO)2] confirm that its net electron donor capacity is superior to that of 2′. A comparison of the complexes of 2′ and 6′ reveals two pronounced structural differences. [CuX(6′)2] (X = Cl, Br) exhibit more acute C‒Cu‒C bond angles than [CuX(2′)2]. In contrast to [CuCl(2′)], [CuCl(6′)] aggregates through Cu···Cu contacts of ca. 2.87 Å, compatible with cuprophilic interactions. These differences may be explained by the complementary steric requirements of the t-Bu and the Me substituent of 6′.eng
dcterms.accessRightsopen access
dcterms.bibliographicCitationIn: Molecules. - Basel : MDPI. - 2017, 22(7), 1133, 1-22
dcterms.creatorThie, Charlotte
dcterms.creatorBruhn, Clemens
dcterms.creatorLeibold, Michael
dcterms.creatorSiemeling, Ulrich
dc.relation.doidoi:10.3390/molecules22071133


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