2-Thiopyridone: X-ray and neutron diffraction study

Ohms, U.; Guth, Hans P.; Kutoglu, A.; Scheringer, C.

doi:10.1107/s0567740882004166

Cited by 72 publications

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“…atoms is 148.22(6)", while the angle N(1)-Sn-N(3) between to those found in the pure thione (45), as well as to those of the the mutually cis nitrogen atoms is 80.0(2)". The angles lattice thione in [CU(C~H~NS)~](C~O~).~C~H~N (46), and…”

mentioning

confidence: 93%

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

Damude¹,

Dean²,

Manivannan³

et al. 1990

Can. J. Chem.

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. Tin metal reacts with 2,2'-dithiobis (pyridine) in refluxing toluene to give the pyridine-2-thiolate complex Sn(C5H4NS)4, l a . Multinuclear ( 7 7~e , '''sn) magnetic resonance shows that ligand redistribution occurs in l~: s n ( E P h )~ (E = S or Se) mixtures to give Sn(EPh)4-,(C5H4NS)x. From the pattern of the "'~n chemical shifts of these series, compared with that of Sn(EPh),-,(SR), (R = simple alkyl or aryl group), the complexes are shown to be five-coordinate Sn(EPh)3(C5H4NS-N,S) when x = 1 and six-coordinate Sn(EPh)4-x(C4H4NS-S)x-2(C5H4NS-N,S)2 when x = 2-4. Reaction of Sn(SPh)' and (C5H&!S)2 yields pure Sn(SPh)2(C5H4NS)2. The 13C NMR spectrum of Sn(C5H4NS-S)2 (C5H4NS-N,S)' is an exchange average down to 178 K, probably as a result of fluxionality. The series Sn(EPh)4-x(L')x (E = Se, L' = 5-nitropyridine-or quinoline-2-thiolate, x = 0-4; E = S or Se, L' = pyridine-2-thiolate-N-oxide, x = 0-2) can beprepared insitu by redox between Sn(EPh)4 and the disulfide (L1)'. Treatment of l a with X2 (X = Br or E-gives SnX4-,(C5H4NS-N,S), (x = 2 or 3), which have been characterized by NMR, and provides a new synthesis of the known dihalo complexes.In a recrystallization of l a from CH2C12:hexane Sn(C5H4NS)4.CsH5NS, 2, was obtained, probably as a result of hydrolysis. The structure of 2 has been solved by single crystal X-ray diffraction techniques. The compound crystallizes in the orthorhombic space group Pbca (No. 61) with a unit cell of dimensions a = 17.132 (2) L'Ctain mitallique rCagit avec la 2,2'-dithiobis (pyridine), dans le tolukne au reflux, pour donner le complexe pyridine-2-thiolate, Sn(C5H4NS)4, l a . La rtsonance magnktique multi-noyaux ( 7 7~e , "'~n) dCmontre que, dans des mClanges de l a : Sn(EPh)4 oh E = S ou Se, il se produit une redistribution des ligands et la formation de composts du type Sn(EPh)4-,(C5H4NS)x. En se basant sur une comparaison des dtplacements chimiques du "' Sn dans les composCs de cette strie avec ceux obsewks dans les produits Sn(EPh),-,(SR), ou R = groupements aryles ou alkyles simples, on a dCmontrC que, si x = I, les complexes sont les entitCs penta-coordonnCes Sn(EPh)3(C5H4NS-N,S) alors que, si x = 2-4, les complexes sont les entitks hexa-coordonn6es Sn(EPh)4-X(C5H4NS-S)2. La reaction du Sn(SPh)' avec le (C5H$JS)2 fournit du Sn(SPh)2(C5HflS)2 a 1'Ctat pur. M&me lorsqu'on abaisse la tempkrature jusqu'i 178 K, le spectre rmn du 13C du Sn(C5H4NS-S)2(C5H4NS-N,S)2 est un spectre moyen rCsultant probablement d'un mtcanisme de fluxion. Faisant appel a une rCaction redox in situ entre l e Sn(EPh)4, et le disulfure (L1)', on peut prCparer les produits de la sCrie Sn(EPh)4-,(L')x (E = Se, L' = 5-nitropyridine-ou quinolkine-2-thiolate, x = 0-4; E = S ou Se, ' L' = pyridine-2-thiolate N-oxyde, x = 0-2). Le traitement du produit l a par du X2 (X = Br ou I) fournit les complexes SnX4-,(C5H4NS-N,S), (x = 2 ou 3) que I'on a caractCrists par rmn; ces rkactions fournissent une nouvelle synthkse de ces complexes dihalogCnCs connus.Lors de la recristallisation du produit l a dans un mClange...

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mentioning

confidence: 93%

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

Damude¹,

Dean²,

Manivannan³

et al. 1990

Can. J. Chem.

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“…The crystal structure of 2-pyridone was first described by Penfold (1953), in an unusual setting (Ohms et al, 1982a). Detailed structural knowledge on the tautomeric 3-hydroxypyridine (Ohms et al, 1983) as well as on the analogous 2-thiopyridone (Ohms et al, 1982b) is available.…”

Section: Introductionmentioning

confidence: 98%

2-Pyridone, C₅H₅NO, crystal structure refinements at 295 Κ and 120 Κ, experimental and theoretical deformation density studies

Ohms¹,

Guth²,

Hellner³

et al. 1984

Zeitschrift Für Kristallographie - Crystalline Materials

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2-Pyridone, C 5 H 5 NO, has been studied by single crystal diffraction at 295 Κ and 120 Κ using X-ray and neutron diffraction methods. The crystal structure of this compound was first studied by Penfold [Acta Crystallogr. 6, 591 -600 (1953)] but described in an unusual setting. We confirmed this structure at both temperatures and refined the structure in the usual setting. Deformation density studies based on the 120 Κ data were performed using the multipole and charge cloud models. They are compared with the theoretical (4 -31G + BF) dynamic deformation density.

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“…The 2MP isomer is known to be dominant in vapor, whereas the 2TP form dominates in polar solvents. In non-polar solvents, there exists an equilibrium between the two isomers and the solid is known to be a 2TP dimer 41,42 . Several studies have reported that 2TP undergoes ESPT forming the thiol 2MP 38,43 .…”

Section: Introductionmentioning

confidence: 99%

Picosecond sulfur K-edge X-ray absorption spectroscopy with applications to excited state proton transfer

Kuiken

Ross

Strader

et al. 2017

Structural Dynamics

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Picosecond X-ray absorption (XA) spectroscopy at the S K-edge (∼2.4 keV) is demonstrated and used to monitor excited state dynamics in a small organosulfur molecule (2-Thiopyridone, 2TP) following optical excitation. Multiple studies have reported that the thione (2TP) is converted into the thiol (2-Mercaptopyridine, 2MP) following photoexcitation. However, the timescale and photochemical pathway of this reaction remain uncertain. In this work, time-resolved XA spectroscopy at the S K-edge is used to monitor the formation and decay of two transient species following 400 nm excitation of 2TP dissolved in acetonitrile. The first transient species forms within the instrument response time (70 ps) and decays within 6 ns. The second transient species forms on a timescale of ∼400 ps and decays on a 15 ns timescale. Time-dependent density functional theory is used to identify the first and second transient species as the lowest-lying triplet states of 2TP and 2MP, respectively. This study demonstrates transient S K-edge XA spectroscopy as a sensitive and viable probe of time-evolving charge dynamics near sulfur sites in small molecules with future applications towards studying complex biological and material systems.

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2-Thiopyridone: X-ray and neutron diffraction study

Cited by 72 publications

References 1 publication

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

2-Pyridone, C₅H₅NO, crystal structure refinements at 295 Κ and 120 Κ, experimental and theoretical deformation density studies

Picosecond sulfur K-edge X-ray absorption spectroscopy with applications to excited state proton transfer

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2-Thiopyridone: X-ray and neutron diffraction study

Cited by 72 publications

References 1 publication

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C5H4NS)4•C5H5NS

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C5H4NS)4•C5H5NS

2-Pyridone, C5H5NO, crystal structure refinements at 295 Κ and 120 Κ, experimental and theoretical deformation density studies

Picosecond sulfur K-edge X-ray absorption spectroscopy with applications to excited state proton transfer

Contact Info

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Resources

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Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

Synthesis and multinuclear magnetic resonance study of some tin(IV) complexes of pyridine-2-thiolate and related ligands, and the X-ray structural analysis of Sn(C₅H₄NS)₄•C₅H₅NS

2-Pyridone, C₅H₅NO, crystal structure refinements at 295 Κ and 120 Κ, experimental and theoretical deformation density studies