Co-crystal synthesis of 2- and 4-mercaptopyridines with thiourea and its analogue, trithiocyanuric acid

Wzgarda-Raj, Kinga; Książkiewicz, Olga; Palusiak, Marcin

doi:10.1039/d2ce00592a

Cited by 6 publications

(4 citation statements)

References 43 publications

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“…It is also worth mentioning that the spontaneous in situ synthesis of mercaptopyridine sulfides from 3-and 4-mercaptopyridine has been reported recently (Wzgarda-Raj et al, 2021a,b), together with a proposed mechanism (Wzgarda-Raj et al, 2021a). In addition, it has been demonstrated that spontaneous in situ sulfide generation takes place under light conditions (Wzgarda-Raj et al, 2022). The three PTP(+) crystal structures deposited in the Cambridge Structural Database (CSD; Groom et al, 2016) are shown in Fig.…”

Section: Introductionmentioning

confidence: 80%

1-(Pyridin-4-yl)-4-thiopyridine (PTP) in the crystalline state – pure PTP and a cocrystal and salt

Wzgarda-Raj,

Wlaźlak,

Ksiąźkiewicz

et al. 2023

Acta Crystallogr C

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The first in situ preparation and single-crystal structure identification of pure 1-(pyridin-4-yl)-4-thiopyridine (PTP), C10H8N2S, a simple and basic derivative of mercaptopyridine, from a crystallization mixture is described. The same PTP was found in two multicomponent crystal forms with 3,5-dinitrobenzoic acid as a classic two-component cocrystal, namely, 1-(pyridin-4-yl)-4-thiopyridine–3,5-dinitrobenzoic acid (1/1), C7H4N2O6·C10H8N2S, and with 2-hydroxy-3,5-dinitrobenzoic acid as a salt formed via proton transfer from the hydroxy group of the acid to the pyridyl N atom of PTP, namely, 4-(4-sulfanylidene-1,4-dihydropyridin-1-yl)pyridin-1-ium 1-carboxy-3,5-dinitrophenolate, C10H9N2S+·C7H3N2O7 −. The protonation energy of PTP is 944.64 kJ mol−1, indicating slightly greater N-basicity compared to pyridine, a well characterized and very basic chemical reference. A variety of molecular interactions can be observed in the three new crystal structures of PTP, which are all discussed in detail. Our findings confirm those of previous studies, indicating that PTP and 4-mercaptopyridine may, under suitable conditions, be chemically converted to one another, and that this process can be stimulated by light (UV–Vis).

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Section: Introductionmentioning

confidence: 80%

1-(Pyridin-4-yl)-4-thiopyridine (PTP) in the crystalline state – pure PTP and a cocrystal and salt

Wzgarda-Raj,

Wlaźlak,

Ksiąźkiewicz

et al. 2023

Acta Crystallogr C

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“…This interaction connects the thiourea molecules. An analysis of the structural properties collected for such contacts found in thiourea crystal structures deposited at the Cambridge Structural Database (CSD; Groom et al, 2016) has been performed in a previous article (Wzgarda-Raj et al, 2022).…”

Section: Figurementioning

confidence: 99%

The pattern of bifurcated hydrogen bonds in thiourea cocrystals with diazine derivatives: experimental and quantum theoretical studies

Wzgarda-Raj,

Olszewski,

Palusiak

2024

Acta Crystallogr C Struct Chem

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Cocrystals of thiourea with pyrazine N-oxide as thiourea–pyrazine N-oxide (2/1), C4H4N2O·2CH4N2S, (I), and with phenazine as thiourea–phenazine (6/7), 7C12H8N2·6CH4N2S, (II), both crystallize in the monoclinic space group P21/c. In the crystalline state, molecules of both components are linked by N—H...N hydrogen bonds. In addition, there are R 2 2(8) hydrogen-bond synthons between thiourea molecules in both crystal structures. Furthermore, bifurcated hydrogen bonds between the –NH groups in the thiourea molecule and the N and O atoms in the N-oxide ring [in (I)], as well as the N atom in the central phenazine ring [in (II)], play a significant role in both structures. This emerging motif was thoroughly examined using quantum chemistry methods.

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“…Mercaptopyridine is a thiol compound with C 5 H 5 NS chemical formula that contains more than one hetero atom (i.e., S and N atoms) [ [28] , [29] , [30] ]. Mercaptopyridine derivatives are examples of organosulfur compounds that possess an important role in industry, pharmacology, and biology [ 31 ]. By dint of such hetero atoms, Mercaptopyridine derivatives gain the π-acidic nature, which imputes their promising role in coordination chemistry [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

Elucidating the adsorption of 2-Mercaptopyridine drug on the aluminum phosphide (Al12P12) nanocage: A DFT study

Rady¹,

Moussa²,

Mohamed³

et al. 2023

Heliyon

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Co-crystal synthesis of 2- and 4-mercaptopyridines with thiourea and its analogue, trithiocyanuric acid

Abstract: This article describes the synthesis of four new co-crystals obtained via cross-crystallisation of 2- and 4-mercaptopyridine with thiourea and trithiocyanuric acid, and examines their crystal structures. The resulting structures are...

Cited by 6 publications

References 43 publications

1-(Pyridin-4-yl)-4-thiopyridine (PTP) in the crystalline state – pure PTP and a cocrystal and salt

1-(Pyridin-4-yl)-4-thiopyridine (PTP) in the crystalline state – pure PTP and a cocrystal and salt

The pattern of bifurcated hydrogen bonds in thiourea cocrystals with diazine derivatives: experimental and quantum theoretical studies

Elucidating the adsorption of 2-Mercaptopyridine drug on the aluminum phosphide (Al12P12) nanocage: A DFT study

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