Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands

Vadim A. Soloshonok; Taizo Ono; Hisanori Ueki; Nicolas Vanthuyne; Teodor Silviu Balaban; Jochen Buerck; Heike Fliegl; Wim Klopper; Jean-Valere Naubron; Tam T. T. Bui; Alex F. Drake; Christian Roussel

doi:10.1021/ja103296g

Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands

Vadim A. Soloshonok, Taizo Ono, Hisanori Ueki, Nicolas Vanthuyne, Teodor Silviu Balaban, Jochen Buerck, Heike Fliegl, Wim Klopper, Jean-Valere Naubron, Tam T. T. Bui, Alex F. Drake, Christian Roussel

Institute of Pharmaceutical Science

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39 Citations (Scopus)

Abstract

Binuclear square planar Ni(II) complexes are described, formed by two tridentate ligands with two imine-nitrogens coordinating two nickel atoms. Such complexes are synthetically readily available with great structural variety and present new types of ridge-tile-like chiral compounds that are reasonably stable in the appropriate "bent" conformation. Enantiomerically pure samples of these compounds have been obtained for the first time using HPLC with a chiral stationary phase. Absolute configurations and chiroptical properties are fully characterized by ECD, VCD, ORD spectroscopy, and theoretical calculations. These new compounds with ridge-tile-like chiral topology are configurationally reasonably stable [Delta G double dagger = 121.4 kJ mol(-1), t(1/2) = 14.9 h (78 degrees C, ethanol)], and therefore their chemistry, physical properties, and applications can be systematically studied.

Original language	English
Pages (from-to)	10477 - 10483
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	132
Issue number	30
DOIs	https://doi.org/10.1021/ja103296g
Publication status	Published - 4 Aug 2010

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Soloshonok, V. A., Ono, T., Ueki, H., Vanthuyne, N., Balaban, T. S., Buerck, J., Fliegl, H., Klopper, W., Naubron, J.-V., Bui, T. T. T., Drake, A. F., & Roussel, C. (2010). Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands. Journal of the American Chemical Society, 132(30), 10477 - 10483. https://doi.org/10.1021/ja103296g

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title = "Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands",

abstract = "Binuclear square planar Ni(II) complexes are described, formed by two tridentate ligands with two imine-nitrogens coordinating two nickel atoms. Such complexes are synthetically readily available with great structural variety and present new types of ridge-tile-like chiral compounds that are reasonably stable in the appropriate {"}bent{"} conformation. Enantiomerically pure samples of these compounds have been obtained for the first time using HPLC with a chiral stationary phase. Absolute configurations and chiroptical properties are fully characterized by ECD, VCD, ORD spectroscopy, and theoretical calculations. These new compounds with ridge-tile-like chiral topology are configurationally reasonably stable [Delta G double dagger = 121.4 kJ mol(-1), t(1/2) = 14.9 h (78 degrees C, ethanol)], and therefore their chemistry, physical properties, and applications can be systematically studied.",

author = "Soloshonok, {Vadim A.} and Taizo Ono and Hisanori Ueki and Nicolas Vanthuyne and Balaban, {Teodor Silviu} and Jochen Buerck and Heike Fliegl and Wim Klopper and Jean-Valere Naubron and Bui, {Tam T. T.} and Drake, {Alex F.} and Christian Roussel",

year = "2010",

month = aug,

day = "4",

doi = "10.1021/ja103296g",

language = "English",

volume = "132",

pages = "10477 -- 10483",

journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society",

number = "30",

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Soloshonok, VA, Ono, T, Ueki, H, Vanthuyne, N, Balaban, TS, Buerck, J, Fliegl, H, Klopper, W, Naubron, J-V, Bui, TTT , Drake, AF & Roussel, C 2010, 'Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands', Journal of the American Chemical Society, vol. 132, no. 30, pp. 10477 - 10483. https://doi.org/10.1021/ja103296g

Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands. / Soloshonok, Vadim A.; Ono, Taizo; Ueki, Hisanori et al.
In: Journal of the American Chemical Society, Vol. 132, No. 30, 04.08.2010, p. 10477 - 10483.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands

AU - Soloshonok, Vadim A.

AU - Ono, Taizo

AU - Ueki, Hisanori

AU - Vanthuyne, Nicolas

AU - Balaban, Teodor Silviu

AU - Buerck, Jochen

AU - Fliegl, Heike

AU - Klopper, Wim

AU - Naubron, Jean-Valere

AU - Bui, Tam T. T.

AU - Drake, Alex F.

AU - Roussel, Christian

PY - 2010/8/4

Y1 - 2010/8/4

N2 - Binuclear square planar Ni(II) complexes are described, formed by two tridentate ligands with two imine-nitrogens coordinating two nickel atoms. Such complexes are synthetically readily available with great structural variety and present new types of ridge-tile-like chiral compounds that are reasonably stable in the appropriate "bent" conformation. Enantiomerically pure samples of these compounds have been obtained for the first time using HPLC with a chiral stationary phase. Absolute configurations and chiroptical properties are fully characterized by ECD, VCD, ORD spectroscopy, and theoretical calculations. These new compounds with ridge-tile-like chiral topology are configurationally reasonably stable [Delta G double dagger = 121.4 kJ mol(-1), t(1/2) = 14.9 h (78 degrees C, ethanol)], and therefore their chemistry, physical properties, and applications can be systematically studied.

AB - Binuclear square planar Ni(II) complexes are described, formed by two tridentate ligands with two imine-nitrogens coordinating two nickel atoms. Such complexes are synthetically readily available with great structural variety and present new types of ridge-tile-like chiral compounds that are reasonably stable in the appropriate "bent" conformation. Enantiomerically pure samples of these compounds have been obtained for the first time using HPLC with a chiral stationary phase. Absolute configurations and chiroptical properties are fully characterized by ECD, VCD, ORD spectroscopy, and theoretical calculations. These new compounds with ridge-tile-like chiral topology are configurationally reasonably stable [Delta G double dagger = 121.4 kJ mol(-1), t(1/2) = 14.9 h (78 degrees C, ethanol)], and therefore their chemistry, physical properties, and applications can be systematically studied.

U2 - 10.1021/ja103296g

DO - 10.1021/ja103296g

M3 - Article

SN - 1520-5126

VL - 132

SP - 10477

EP - 10483

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 30

ER -

Ridge-Tile-like Chiral Topology: Synthesis, Resolution, and Complete Chiroptical Characterization of Enantiomers of Edge-Sharing Binuclear Square Planar Complexes of Ni(II) Bearing Achiral Ligands

Abstract

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