Induced chirality-at-metal and diastereoselectivity at Δ/Λ-configured distorted square-planar copper complexes by enantiopure Schiff base ligands: combined circular dichroism, DFT and X-ray structural studies

Dalton Transactions : an International Journal of Inorganic Chemistry
Mohammed EnamullahChristoph Janiak

Abstract

Bidentate enantiopure Schiff base ligands, (R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldiminato-κ(2)N,O, diastereoselectively yield Δ/Λ-chiral four-coordinated, non-planar Cu(N^O)2 complexes [Ar = C6H5 R/S-L1, m-C6H4OMe R-L2, p-C6H4OMe R/S-L3, and p-C6H4Br R/S-L4]. Two N,O-chelate ligands coordinate to the copper(II) atom in distorted square-planar mode, and induce metal-centered Δ/Λ-chirality at the copper atom in the C2-symmetric complexes. In the solid state, the R-L1 (or R-L4) ligand chirality diastereoselectively induces a Λ-Cu configuration in Λ-Cu-R-L1 (or Λ-Cu-R-L4), the S-L1 ligand a Δ-Cu configuration in Δ-Cu-S-L1, forming enantiopure crystals upon crystallization. Conversely, the R-L2 ligand combines both Λ/Δ-Cu-R-L2 as a diastereomeric pair in the crystals. In solution, electronic circular dichroism (CD) spectra show full or partial diastereoselectivity towards Λ-Cu for R ligands and towards Δ-Cu for S ligands. The electronic CD spectra measured on all complexes obtained from R ligands (or S ligands), e.g. Cu-R-L1, Cu-R-L2, Cu-R-L3, and Cu-R-L4 (or Cu-S-L1, Cu-S-L3, and Cu-S-L4), show consistent spectral features. TDDFT calculations of the electronic CD spectra for the diastereomers Λ-Cu-R-L1 and Δ-Cu-R-L1 suggest that t...Continue Reading

References

Aug 6, 2000·Acta Crystallographica. Section A, Foundations of Crystallography·H D Flack, G Bernardinelli
Apr 10, 2003·Journal of the American Chemical Society·Glenn M Sammis, Eric N Jacobsen
Aug 14, 2003·Chemical Reviews·Harald Gröger
Aug 12, 2004·Journal of the American Chemical Society·Glenn M SammisEric N Jacobsen
Sep 9, 2004·Chemical Society Reviews·Pier Giorgio Cozzi
Dec 8, 2004·Acta Crystallographica. Section C, Crystal Structure Communications·Takashiro Akitsu, Yasuaki Einaga
Feb 20, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Lei YangRobert P Houser
Aug 31, 2007·Chemical Communications : Chem Comm·Kazuhiro MatsumotoTsutomu Katsuki
Oct 10, 2007·Chirality·H D Flack, G Bernardinelli
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Dec 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Jen-Jeh LeeJwu-Ting Chen
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Mar 19, 2009·Chemical Communications : Chem Comm·Suzanne E HowsonPeter Scott
May 7, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Christoph JaniakMohammed Enamullah
May 7, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Jochen NiemeyerGerhard Erker
May 14, 2009·Accounts of Chemical Research·Masakatsu ShibasakiNaoya Kumagai
Feb 18, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Jan M BeckerPeter Scott
May 4, 2010·Chemistry : a European Journal·William CleggRiccardo Pasquale
Jun 5, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Anaïs ZulaufEmmanuelle Schulz
Sep 18, 2010·Organic Letters·Eduardo C Escudero-AdánArjan W Kleij
Sep 30, 2010·Chemical Communications : Chem Comm·Beatriz Gil-HernándezChristoph Janiak
Dec 22, 2010·Acta Crystallographica. Section A, Foundations of Crystallography·H D FlackD J Watkin
Jun 17, 2011·Chemical Society Reviews·Gennaro PescitelliNina Berova
Dec 4, 2012·Physical Chemistry Chemical Physics : PCCP·Gennaro PescitelliFabrizio Santoro
Jun 8, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·André KelchPeter G Jones

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Citations

Dec 1, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Mohammed EnamullahChristoph Janiak
Apr 29, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Xue-Quan ZhouShi-Ping Yan
Feb 20, 2015·Inorganic Chemistry·Anne-Christine ChamayouSteffen Lüdeke
May 6, 2020·Physical Chemistry Chemical Physics : PCCP·Irina OsadchukEric Clot
May 4, 2017·Annual Review of Physical Chemistry·Monika Srebro-Hooper, Jochen Autschbach
Jun 9, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Nazanin KordestaniMohammed Enamullah
Jun 16, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Mohammed EnamullahChristoph Janiak
Sep 16, 2021·Angewandte Chemie·Dipankar GhoshKrishna K Damodaran

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