Synthesis, redox properties, and molecular structure of 4,5-diethylthio-4-cyclopenten-1,3-dione: Cyclic voltammetric evidence for a kinetically stable radical anion View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2006-01

AUTHORS

William H. Watson, Guanmin Wu, Praveen Vadapally, Michael G. Richmond

ABSTRACT

The preparation of the new disulfide compound 4,5-diethylthio-4-cyclopenten-l,3-dione (1) from 4,5-dichloro- 4-cyclopenten-l,3-dione and ethanethiol is described. The title compound has been isolated and characterized in solution by IR and NMR spectroscopies, and the solid-state structure solved by X-ray crystallography. 4,5-Diethylthio-4-cyclopenten-l,3-dione crystallizes in the triclinic space group P-l, a = 7.230(4) Å, b = 8.191(5) Å, c = 10.187(6) Å, α = 108.48(1)°, β = 97.75(1)°, γ = 105.90(1)°, V = 533.8(6) Å3, Z = 2, and dcalc = 1.346 Mg/m3; R = 0.0406, Rw = 0.0967 for 1394 reflections with I > 2σ(I). The redox properties of 4,5-diethylthio-4-cyclopenten-l,3-dione have been examined by cyclic voltammetry in CH2C12 solution, where a reversible one-electron reduction was found. The reduction behavior of the diethylthio derivative is discussed relative to the closely related 4,5-bis(p-tolylthio)-4-cyclopenten-l,3-dione, whose radical anion exhibits quasi-reversible reduction behavior due to competitive C(dione ring)–S bond cleavage. The differences in the electrochemical behavior of the two disulfides are discussed with respect to the ancillary R group. More... »

PAGES

55-60

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s10870-005-9023-y

DOI

http://dx.doi.org/10.1007/s10870-005-9023-y

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1049804684


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