Investigation of Structural Relationships between Racemic Alkali and Ammonium Hydrogen Tartrates and their Chiral Counterparts

Abstract

Single crystals of racemic anhydrous alkali and ammonium hydrogen tartrates of the composition M(C4H5O6) with M = K, Rb, Cs, NH4 as well as MxM′1−x(C4H5O6) with {M = K, M′ = Rb, x = 0.5}, {M = K, M′ = NH4, x = 0.56} and {M = Rb, M′ = NH4, x = 0.61} were obtained from the reaction of D,L‐tartaric acid with the corresponding hydroxides MOH and / or M′OH. These compounds form an isostructural series (monoclinic, P21/c, Z = 4). The structures consist of alternating tartrate anion layers and cation layers. Each tartrate layer is held together by a number of hydrogen bonds and contains exclusively either the D or the L‐form of the tartrate. Structural analogies between these crystals and their chiral counterparts are investigated. The smilarity of cell parameters between racemic and chiral structures is shown to be a consequence of certain packing features that occur in both groups.

Structural systematics of 4,4′-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures

“…This interrelationship also extends to analogues of carbamazepine. The present results enhance our conviction, drawn from some published observations (Vrcelj et al, 2003;Gelbrich et al, 2004;Gerber et al, 2004;Gelbrich & Hursthouse, 2005;Aragoni et al, 2007) and many unpublished ones, of the widespread occurrence, perhaps extending even to universality, of this phenomenon. The 133 crystal structures of benzenesulfonamidobenzenes forming the present set are elaborated from only nine basic supramolecular connectivity motifs.…”

“…Many large sets of structures have been examined in these studies, including alkali metal dicarboxylates, chalcones, benzamides, pyridine amides, pyridine sulfonamides, sulfathiazole solvates, tricyclics related to carbamazepine, amine tartrates and alkali metal tartrates. Of these, only part of the work on the alkali metal tartrates (Gelbrich et al, 2004(Gelbrich et al, , 2006a, and the crystal structure of an aberrant product encountered in the present work (Gelbrich et al, 2006b) have so far been published. The present set has been chosen as the first report from this study because of its completeness and relative simplicity of distribution of crystal structure types amongst the compounds in the set.…”

Rediscovering Pasteur's Quasiracemates

“…Each bitartrate and bimalate component participates in strong CO 2 H⋅⋅⋅ − O 2 C interactions with translationally related neighbors to give homomeric 1D chains along the a axis (Figure 4 a). These motifs are antiparallel and are further linked through OH⋅⋅⋅ − O 2 C and N + H⋅⋅⋅O contacts to give a molecular assembly that mimics the previously reported centrosymmetric structure of ammonium (±)‐bitartrate (space group P 2 1 / c ) 13…”

Reversible Layer‐by‐Layer Deposition on Solid Substrates Inspired by Mussel Byssus Cuticle

“…Zwitterionic λ 5 Si, λ 5 Si′ disilicates containing SiO 4 C skeletons with five‐ring chelates made up of hydroxy‐ and carboxy‐oxygen atoms have recently been investigated 6. Complexes of tartaric acid are also known with elements such as lithium,7,8 antimony,9 bismuth,10 vanadium,11,12 copper,13 cobalt,14 and samarium 15. In each of these compounds, the central metal is coordinated by the most acidic carboxy‐oxygen atom and the α‐hydroxy group.…”