Sulfur extrusion and sulfur oxidation of 2,2′-dithiodibenzoic acid in combination with Cu(II) ion and in the absence of co-ligands: Structural, spectroscopic and thermogravimetric evidence

A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

“…1(b). Such oxidation of the original 2-thiobenzoic acid to DTBA is well known in co-crystallization studies (Broker & Tiekink, 2007;Gorobet et al, 2018). In terms of stoichiometry, the formation of the title 1:2 co-crystal is consistent with the 1:1 stoichiometry of the original grinding experiment.…”

Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]

“…Recent studies of co-crystals designed to incorporate n-mercaptobenzoic acid as a conformer [10,11] resulted in unexpected outcomes, e.g. oxidation of the thiol, a well known phenomenon for n-mercaptobenzoic acids [12], and desulfurization [13], again observed previously [14]. As a follow up to these studies, a co-crystallization experiment between an authenticated [5] sample of (2-py)-CH=N-C 6 H 10 -N=CH-(2-py) and 3-mercaptobenzoic acid was undertaken which lead to the isolation of the title 1:2 salt, that is, [H 3 NC 6 H 10 NH 3 ]: 2[C 6 H4NO 2 ].…”

“…The hydrogen bond donated by ammonium-N-H1n atoms is bifurcated, effectively bridging O(carboxylate) and N(pyridyl) atoms of the same anion forming a fivemembered {H· · · OC 2 N· · · } synthon [N2-H1n· · · O1 i : H1n· · · O1 i = 2.181(14) Å, N2· · · O1 i = 2.9429(17) Å with angle at H1n = 143.1(12)°; N2-H1n· · · N1 i : H1n· · · N1 i = 2.190(15) Å, N2· · · N1 i = 2.9352(16) Å with angle at H1n = 140.8(12)°; symmetry operation (i) 1 − x, 1 − y, 2 − z]. The H1n· · · O1 edge of this synthon, edge "1", is connected to another edge "1" via a second ammonium-N1-H3n· · · O1 hydrogen bond to form an eight-membered {· · · HNH· · · O} 2 synthon [N2-H3n· · · O1: H3n· · · O1 = 1.889(13) Å, N2· · · O1 = 2.7687 (14) Å with angle at H3n = 170.2(18)°], indicating the carboxylate-O1 atom participates in two hydrogen bonds. The remaining hydrogen bond involves the carboxylate-O2 atom and involves edge "2" of the aforementioned synthon, where two of these are linked into a 12-membered {· · · HNH· · · OCO} 2 synthon [N2-H2n· · · O2 ii : H2n· · · O2 ii = 1.883(15) Å, N2· · · O2 ii = 2.7663(16) Å with angle at H2n = 170.4(13)°; symmetry operation (ii) − x, 1 − y, 2 − z].…”

A 1:1:1 co-crystal solvate comprising 2,2′-dithiodibenzoic acid, 2-chlorobenzoic acid and N,N-dimethylformamide: crystal structure, Hirshfeld surface analysis and computational study

“…One reason for the scarcity of cocrystals containing 2-MBA is the propensity for the acid to be oxidized, to generate DTBA, during co-crystallization experiments with bipyridyl-type molecules (Broker & Tiekink, 2007) and with other carboxylic acids (Tan & Tiekink, 2019a). Another, less common, outcome of crystallization experiments with 2-MBA is the sulfur extrusion product, 2,2 0 -thiodibenzoic acid (Tan & Tiekink, 2018;Gorobet et al, 2018). Herein, ISSN 2056-9890 another unexpected product from a co-crystallization experiment involving 2-MBA is described.…”