Racemic Tartrate/Malate Anions Combine with Racemic Complex Cations to Form Optically Active Ionic Crystals
| Autor: | Takumi Konno, Masashi Uno, Nobuto Yoshinari, Tatsuhiro Kojima, Naoto Kuwamura |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Resolution (electron density) Ionic crystal General Chemistry Tartrate Optically active 010402 general chemistry Crystal engineering 01 natural sciences Catalysis 0104 chemical sciences law.invention chemistry.chemical_compound Crystallography law Crystallization Homochirality Chirality (chemistry) |
| Zdroj: | Chemistry (Weinheim an der Bergstrasse, Germany). 27(32) |
| ISSN: | 1521-3765 |
| Popis: | Spontaneous resolution has attracted continuing attention in various research fields since Pasteur's work on the crystallization behavior of racemic tartrate. Here, a unique example of this phenomenon is reported, involving ionic crystals generated from racemic RR/SS- tartrate or R/S-malate and racemic ΔΔ/ΛΛ-[Ag3 Rh2 (2-aminoethanethiolato)6 ]3+ (ΔΔ/ΛΛ-[1]3+ ) in water. RR- and SS-tartrate selectively recognize the ΛΛ and ΔΔ isomers of [1]3+ to produce ionic crystals of (ΛΛ-[1])2 (RR-tartrate)3 and (ΔΔ-[1])2 (SS-tartrate)3 , respectively, which can undergo spontaneous resolution. While spontaneous resolution also occurs when using R/S-malate, R- and S-malate select the opposite isomers of [1]3+ to give ionic crystals of (ΔΔ-[1])2 (R-malate)3 and (ΛΛ-[1])2 (S-malate)3 , respectively. In the presence of S-aspartate, (ΛΛ-[1])2 (R-tartrate)3 and (ΔΔ-[1])2 (S-tartrate)3 are preferentially crystallized from ΔΔ/ΛΛ-[1]3+ and RR/SS-tartrate at solution pH values of 6 and 10, respectively. This finding provides significant insight into the optical resolution of chemical species by spontaneous resolution and the origin of homochirality in nature. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|