Molecular recognition properties of tartrates and metal‐tartrates in solution and gas phase

Abstract

Solution phase and gas phase chiral molecular recognition properties of tartrates (salts or esters of tartaric acid) and metal tartrates (binuclear tartrato(4-)-metal-bridged complexes) are reviewed in conjunction with their applications in enantiomeric separation science and their mass spectrometric chiral discrimination properties.

New structural insight for antimony(III)-tartrate

“…This structure is similar to that of the binuclear vanadyl tartrate complex, which is often used as a model to explain most of the tartrato(4-) metal complexes [6]. Enantioselective molecular recognition properties of tartar emetic in solution and in the gas phase have often been explained based on this particular geometry [5]. However, explicating our observations [7][8][9][10], particularly the proton-assisted enantioselective character of tartar emetic was not trivial using this particular structure alone.…”

“…Bactericidal activity of tartar emetic at higher concentrations (compared to penicillin) has also been reported [2]. Further, the asymmetric nature of this economical and easily synthesizable anionic metal complex has prompted its use as a chiral resolving agent [5]. Despite initial few reports on its potential capacity as a drug and a resolving agent [1][2][3][4][5][6], further developments of its applications have not materialized.…”

“…Further, the asymmetric nature of this economical and easily synthesizable anionic metal complex has prompted its use as a chiral resolving agent [5]. Despite initial few reports on its potential capacity as a drug and a resolving agent [1][2][3][4][5][6], further developments of its applications have not materialized. This is likely due, in part, to the lack of understanding of its structure and molecular recognition chemistry.…”

The “Bridge” Game: Role of the Fourth Player in Chiral Recognition

“…[1][2][3][4] In recent years, mass spectrometry (MS) proved to be a powerful means for investigating chiral recognition in the gas phase, that is, in the absence of perturbing environmental phenomena. [4][5][6][7][8] The study of isolated chiral clusters may provide some insights into the origin of homochirality in biological systems and into the amazing enantioselectivity of many chiral catalysts, like enzymes. In their seminal work, Fales and Wright first demonstrated the selective selfassociation of homochiral tartrates in the gas phase.…”

Antimony(III)-D, L-tartrates exhibit proton-assisted enantioselective binding in solution and in the gas phase

“…Recent reports by Kass et al show solution phase species are produced and recorded in respective mass spectra when ACN/H 2 O (compared with MeOH/H 2 O) mixtures are employed as the electrospray solvent [17][18][19]. Nevertheless, while metaltartrates have been demonstrated to be useful for enantioselective resolution of a variety of compound classes in the solution phase [16], a general model for describing their relevant binding chemistry is still missing.…”