Spontaneous Resolution of a Triple‐Stranded Dinickel(II) Helicate Generated via Intermolecular Transamination Reaction of<i>S</i>‐Methylisothiocarbohydrazide in the Presence of Ni<sup>2+</sup>

The effect of the metal ion and ligand design on the enantioselectivity and linkage isomerization of neutral cobalt and zinc bisthiosemicarbazone metallohelicates has been investigated in this work. The electrochemical synthesis has afforded the enantioselective formation of chirally pure cobalt helicates, and the ΛΛ isomer of a single enantiomer has been crystallized as only product for the cobalt methyl-substituted thiosemicarbazone helicate. Interestingly linkage isomers have been formed from zinc ethyl-substituted thiosemicarbazone helicate enantiomers for the first time. The co-existence of these isomers has been evaluated from the point of view of both experimental results and computational calculations.

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Effect of the Metal Ion on the Enantioselectivity and Linkage Isomerization of Thiosemicarbazone Helicates

Romero

Suárez

Fernández-Fariña

et al. 2017

Chemistry A European J

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Solution‐Stable Triple Helicates of Quaterimidazole: Three‐Dimensional Crystal Structures and Optical Resolution by Chiral‐Column HPLC

et al. 2011

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Complex formation of quaterimidazole with FeII, CoII, and NiII yielded dinuclear triple helicates in the solution state by the self‐assembling ability of the ligand based on the strong chelating coordination bonds. Crystallization of the CoII complex from aqueous solution afforded the CoIII complex with a triple‐helical structure. X‐ray crystal structure analyses revealed that the helicates are linked through N–H···X hydrogen bonds with counteranions and solvent molecules to form three‐dimensional networks. The spectrophotometric titration experiment showed that quaterimidazole forms triple helicates with various d‐block transition metal ions with high selectivity. The outward intermolecular interactions and high stability of the helicates from the rigid molecular structures combined with the intramolecular π–π interactions of imidazole moieties and their strong chelating coordination enabled the successful optical resolution of right‐ and left‐handed helicates by chiral‐column HPLC.

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Coordination versatility of 1,5-bis(salicylidene)carbohydrazide in Ni(II) complexes

Sutradhar

Barman

Rentschler

2014

Inorganic Chemistry Communications

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Spontaneous Resolution of a Triple‐Stranded Dinickel(II) Helicate Generated via Intermolecular Transamination Reaction ofS‐Methylisothiocarbohydrazide in the Presence of Ni²⁺

Abstract: Keywords: Triple-stranded helicates / Nickel(II) / Spontaneous resolution / Chiroptical properties / Magnetic properties

Cited by 7 publications

References 35 publications

Effect of the Metal Ion on the Enantioselectivity and Linkage Isomerization of Thiosemicarbazone Helicates

Effect of the Metal Ion on the Enantioselectivity and Linkage Isomerization of Thiosemicarbazone Helicates

Solution‐Stable Triple Helicates of Quaterimidazole: Three‐Dimensional Crystal Structures and Optical Resolution by Chiral‐Column HPLC

Coordination versatility of 1,5-bis(salicylidene)carbohydrazide in Ni(II) complexes

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Spontaneous Resolution of a Triple‐Stranded Dinickel(II) Helicate Generated via Intermolecular Transamination Reaction ofS‐Methylisothiocarbohydrazide in the Presence of Ni2+

Abstract: Keywords: Triple-stranded helicates / Nickel(II) / Spontaneous resolution / Chiroptical properties / Magnetic properties

Cited by 7 publications

References 35 publications

Effect of the Metal Ion on the Enantioselectivity and Linkage Isomerization of Thiosemicarbazone Helicates

Effect of the Metal Ion on the Enantioselectivity and Linkage Isomerization of Thiosemicarbazone Helicates

Solution‐Stable Triple Helicates of Quaterimidazole: Three‐Dimensional Crystal Structures and Optical Resolution by Chiral‐Column HPLC

Coordination versatility of 1,5-bis(salicylidene)carbohydrazide in Ni(II) complexes

Contact Info

Product

Resources

About

Spontaneous Resolution of a Triple‐Stranded Dinickel(II) Helicate Generated via Intermolecular Transamination Reaction ofS‐Methylisothiocarbohydrazide in the Presence of Ni²⁺