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. 2025 Mar 24;64(11):5487-5494.
doi: 10.1021/acs.inorgchem.4c05384. Epub 2025 Feb 10.

Water-Mediated Chiral Resolution of Ag-NHC(Nucleobase) Complexes

Alvaro Polo  1 , Ricardo Rodríguez  1 , Ramón Macías  1 , Daniel Cobo Paz  1 , Pablo J Sanz Miguel  1
Affiliations

Water-Mediated Chiral Resolution of Ag-NHC(Nucleobase) Complexes

Alvaro Polo et al. Inorg Chem. .

Abstract

This study reveals a novel role of water as a chiral inducer, demonstrating its ability to drive the asymmetric resolution of prochiral silver-nucleobase complexes. During crystallization, helical water columns spontaneously form, selectively recognizing one enantiomer of the silver complex. This enantiospecific interaction drives the separation of the P and M enantiomers, leading to the formation of enantiopure crystals, whose chirality was confirmed through X-ray crystallography.

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Figures

1
1. Formation of Compounds 1, 2[OTf]2, 2[Br]2, and 3
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1
VT 1H NMR spectra (CD2Cl2, 400 MHz) of 3.
2
2
View of 1 with atom numbering scheme.
3
3
Front view of cation 2 in 2[OTf]2.
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4
Detail of the host–guest system {Br,MeOH ⊂ 2} in 2[Br]2·CH3OH. A Br– anion has been omitted for clarity.
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5
Side view of the (P)-3 enantiomer in 3·2DMSO. For P- and M-chirality see Figure .
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Conceptual depiction of the helical chirality exhibited by the (P)-3 and (M)-3 enantiomers in 3·2DMSO.
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Staggered arrangement of 3 in 3·2DMSO featuring π–π stacking. For P- and M-chirality see Figure .
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Schematic representation of the P-helical backbone within the water cluster of (M)-3·(P)-3H2O. Red dot: oxygen atom.
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Detail of the helical arrangement of 3 in (M)-3·(P)-3H2O around the respective chiral water chains.
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Two enantiomeric helical superstructures within the crystal packings of 3·3H2O.
See this image and copyright information in PMC

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