ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The hydrogen-bond pattern of 4-mercaptopyridine-4-thiopyridone in solution and in the solid state consists of extended chains of 4-thiopyridone associated through NH…S hydrogen bonds. The solution structure in chloroform was studied by UV-visible spectrometry and vapor pressure osmometry. A tautomerization constant of 1 · 8, favoring 4-thiopyridone, and a self-association constant of 2600 ml-1 were determined. Over 50% of the sample is aggregated near saturation with significant amounts (〉15%) of the sample present as oligomers containing four or more 4-thiopyridone monomer units. In its crystal structure, 4-mercaptopyridine-4-thiopyridone is composed of infinite chains of 4-thiopyridone associated by NH…S hydrogen bonds between glide related molecules, with N…S = 3 · 219(3) Å, H…S = 2 · 42(4) Å, N - H…S angle = 175(4)° and H…S = C angle = 96(1)°. Relationships between solution aggregation, crystal nucleation, and crystal propagation are discussed. Crystal data are as follows: space group = P21/c, a = 7 · 183(5) Å, b = 6 · 132(5) Å, c = 11 · 618(7) Å, β = 90 · 51(5)°, Z = 4, Dc = 1 · 44 g cm-3, 1623 reflections, R = 0 · 050, Rw = 0 · 072.
Additional Material:
9 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610050404
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