reactions of thiols

PubMed Google Scholar. volume 43, pages319–346(2007)Cite this article. Shirini, F., Zolfigol, M.A., Lakouraj, M.M., and Azadbar, M.R., Russ. Kumar, P., Rao, T.A., and Pandey, B., J. Chem. For oxidation reactions, however, this similarity disappears. 33, p. 665. Although the basicity of ethers is roughly a hundred times greater than that of equivalent sulfides, the nucleophilicity of sulfur is much greater than that of oxygen, leading to a number of interesting and useful electrophilic substitutions of sulfur that are not normally observed for oxygen. J. Org. 30, p. 1249. Oxidation would affect the sulphur atom in thiols, whereas in alcohol it would lead to the generation of a new product where it changes the oxidation state of a carbon atom. Nikitina, L.E., Pashagin, A.E., and Plemenkov, V.V., Russ. 31, p. 1477. Res., 1991, vol. [2][3] This reaction is accepted as a click chemistry reaction given the reactions’ high yield, stereoselectivity, high rate, and thermodynamic driving force. Otani, T., Sugihara, Y., Ishii, A., and Nakayama, J., Chem. The final expression has a Gaussian-like shape.[8]. Anisimov, A.V., Tarakanova, A.V., and Tkhanaa Al’-Khaddad, Neftekhimiya, 1999, vol. © 1997-2020 LUMITOS AG, All rights reserved, https://www.chemeurope.com/en/encyclopedia/Thiol.html, Your browser is not current. It is also responsible for some sort of wine faults that have resulted due to some unintended reactions caused between sulphur and yeast. Ross. Alks, Y., Keith, D.D., and Sufrin, R.J., Synthesis, 1992, p. 623. van den Bos, J.C., Vloon, W.J., Koomen, G.-J., and Pandit, U.K., Tetrahedron, 1991, vol. Yoneda, K., Ota, A., and Kawashima, Y., Chem. 28, p. 273. In the biochemistry lab, proteins are often maintained in their reduced (free thiol) state by incubation in buffer containing an excess concentration of b-mercaptoethanol (BME) or dithiothreitol (DTT). Kannan, P., Shayira, H.B., and Pitchumani, K., Proc. In both cases, NADPH is the ultimate electron donor, reducing FAD back to FADH2 in each catalytic cycle. By itself the -SH group is called a mercapto group. 133, p. 79. Pharm., 1993, vol. 41, p. 1283. Palomo, C., Oiarbide, M., Lopez, R., and Gomez-Bengoa, E., Tetrahedron Lett., 2000, vol. 35, p. 1663. 38, p. 232. 35, p. 951. Mal’kina, A.G., Andriyankova, A.G., Nosyreva, V.V., and Trofimov, B.A., Russ. Chem., 1992, vol. Nakata, M., Akiyama, N., Kojima, K., Masuda, H., Kinoshita, M., and Tatsuta, K., Tetrahedron Lett., 1990, vol. [4] The carbon-centered radical can undergo chain-growth polymerization depending on the thiol and ene functional groups. J. Org. Article  J. Org. Org. Cossu, S., De Lucchi, O., Peluso, P., and Volpicelli, R., Synth. The mechanism for this and other similar reactions is not yet completely understood, but evidence points to an initial thiol-disulfide exchange reaction with a pair of cysteines from the enzyme, (phase 1 below) followed by flavin-dependent reduction of the cysteine-cysteine disulfide (phase 2). 29, p. 1321. Estaf’eva, I.T., Levkovskaya, G.G., Bannikova, O.B., and Mirskova, A.N., Zh. and Smirnov, L.D., Khim. Takashira, E., Nakamura, Y., and Fujimoto, K., Tetrahedron Lett., 1999, vol. Imtiaz, M.H. Chem., 1999, vol. Org. Kasavan, V., Bonnet-Delpon, D., and Begue, J.-P., Tetrahedron Lett., 2000, vol. Thiols are usually prepared by using the hydrosulfide anion (-SH) as a neucleophile in an S N 2 reaction with alkyl halides. 113, p. 6317. Chem., 1992, vol. Akad. Thiols are also responsible for a class of wine faults caused by an unintended reaction between sulfur and yeast. Back, G.T., Baron, L.D., and Yangl, K., J. Org. Chem., 2001, vol. Soc., 1991, vol. Therefore, the S-H bond in the thiols have a lower dipole moment as compared to the alcohol's O-H bond. B, 1992, vol. Lee, J.M., Lee, W.-C., Jung, J.H., and Oh, Y.D., Synth. Org. 57, p. 1547. 33, p. 395. Chem., 1999, vol. 64, p. 781. As the functional group of the amino acid cysteine, the thiol group plays an important role in biological systems. Am. 40, p. 7015. Khim. Org. J. Org. He is author of more than 200 publications, including 20 reviews on modern problems of organoelement chemistry. The positive charge on the sulfur also makes it an excellent leaving group, as the resulting product will be a neutral and very stable sulfide. Rodin, A.P., Safarova, G.M., Makaeva, R.M., Zorin, V.V., and Karakhanov, R.A., Zh. Czech. Chem., 1991, vol. 37, p. 297. For more complex substance alkylthio is used instead of alkoxy. [5], Thiol-ene reactions are known to proceed through a Michael addition pathway. 74, p. 1843. 41, p. 561. 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