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doi:10.22028/D291-43412
Titel: | A Cyclic Iminoborane-NHC Adduct: Synthesis, Reactivity, and Bonding Analysis |
VerfasserIn: | Koner, Abhishek Sergeieva, Tetiana Morgenstern, Bernd Andrada, Diego M. |
Sprache: | Englisch |
Titel: | Inorganic Chemistry |
Bandnummer: | 60 |
Heft: | 18 |
Seiten: | 14202-14211 |
Verlag/Plattform: | ACS |
Erscheinungsjahr: | 2021 |
Freie Schlagwörter: | Adducts Aromatic Compounds Boron Carbene Compounds Hydrocarbons |
DDC-Sachgruppe: | 500 Naturwissenschaften |
Dokumenttyp: | Journalartikel / Zeitschriftenartikel |
Abstract: | Lewis-base coordinated iminoborane adducts, in contrast to their isoelectronic analogue imines, remain largely unexplored given the lack of efficient synthetic strategies for generating robust compounds. Herein, we report the preparation of a cyclic amino iminoborane carbene complex 2 obtained in quantitative yield by adding NHC to the 1,8-(trimethylsilyl)- aminonaphthalene complex of boron 1 to induce the elimination of trimethylsilyl chloride (TMSCl). The iminoborane-NHC adduct 2 shows unprecedented thermal stability both in the solid and solution phases, due to the rigid, pre-established geometry of the 1,8-diaminonaphthalene scaffold. Theoretical calculations reveal an exceptionally strong iminoborane-NHC bond as a consequence of the enhanced boron-center acidity in combination with the lower steric and electronic shielding. We show that the chemical bond can be understood as donor−acceptor interaction, leading to a different kind of electronic situation of the BN π-bond. The high conjugation between the pz-lone pair of the tricoordinated sp2 hybridized N atom and the BN π-system results in a particularly long BN double bond distance. Taking advantage of the pendant lone pair of the dicoordinated sp2 hybridized N atom, the iminoborane-NHC adduct gives access to NHC-stabilized borenium cation 3 through the reaction with trimethylsilyl triflate (Me3SiOTf) or to the gallium adduct 4 by reacting with GaCl3. Incorporating an iminoborane functional group into a π-conjugated system brings a new bonding situation for broadening the scope of BN-containing polyaromatic systems. |
DOI der Erstveröffentlichung: | 10.1021/acs.inorgchem.1c01583 |
URL der Erstveröffentlichung: | https://pubs.acs.org/doi/10.1021/acs.inorgchem.1c01583 |
Link zu diesem Datensatz: | urn:nbn:de:bsz:291--ds-434121 hdl:20.500.11880/38924 http://dx.doi.org/10.22028/D291-43412 |
ISSN: | 1520-510X 0020-1669 |
Datum des Eintrags: | 8-Nov-2024 |
Bezeichnung des in Beziehung stehenden Objekts: | Supporting Information |
In Beziehung stehendes Objekt: | https://pubs.acs.org/doi/suppl/10.1021/acs.inorgchem.1c01583/suppl_file/ic1c01583_si_001.pdf |
Fakultät: | NT - Naturwissenschaftlich- Technische Fakultät |
Fachrichtung: | NT - Chemie |
Professur: | NT - Prof. Dr. Guido Kickelbick NT - Prof. Dr. David Scheschkewitz |
Sammlung: | SciDok - Der Wissenschaftsserver der Universität des Saarlandes |
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