Inorganic chemistry,isothiocyanate is afunctional group as found in compounds with the formulaR−N=C=S. Isothiocyanates are the more common isomers ofthiocyanates, which have the formulaR−S−C≡N.
TheN=C andC=S distances are 117 and 158pm.[2] By contrast, inmethyl thiocyanate,N≡C andC−S distances are 116 and 176 pm.
Typicalbond angles forC−N=C in aryl isothiocyanates are near 165°. Again, the thiocyanate isomers are quite different withC−S−C angle near 100°.[3] In both isomers theSCN angle approaches 180°.
Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles.[7] This methodology has been applied to a polymer-supported synthesis of isothiocyanates.[8]
^abcd"Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 April 2017. Retrieved14 April 2019.
^Majewska, Paulina; Rospenk, Maria; Czarnik-Matusewicz, Bogusława; Kochel, Andrzej; Sobczyk, Lucjan; Dąbrowski, Roman (2008). "Structure and polarized IR spectra of 4-isothiocyanatophenyl 4-heptylbenzoate (7TPB)".Chemical Physics.354 (1–3):186–195.Bibcode:2008CP....354..186M.doi:10.1016/j.chemphys.2008.10.024.
^Erian, Ayman W.; Sherif, Sherif M. (1999). "The chemistry of thiocyanic esters".Tetrahedron.55 (26):7957–8024.doi:10.1016/S0040-4020(99)00386-5.
^Emergon, David W. (1971). "The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment".Journal of Chemical Education.48 (1): 81.Bibcode:1971JChEd..48...81E.doi:10.1021/ed048p81.
^Wong, R; Dolman, SJ (2007). "Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts".The Journal of Organic Chemistry.72 (10):3969–3971.doi:10.1021/jo070246n.PMID17444687.
^O'Reilly, RJ; Radom, L (2009). "Ab initio investigation of the fragmentation of 5,5-diamino-substituted 1,4,2-oxathiazoles".Organic Letters.11 (6):1325–1328.doi:10.1021/ol900109b.PMID19245242.
^Burkett, BA; Kane-Barber, JM; O'Reilly, RJ; Shi, L (2007). "Polymer-supported thiobenzophenone : a self-indicating traceless 'catch and release' linker for the synthesis of isothiocyanates".Tetrahedron Letters.48 (31):5355–5358.doi:10.1016/j.tetlet.2007.06.025.
^Hammerich, Ole; Parke, Vernon D. (1977). "The electrochemistry of cyanates and related compounds". In Patai, Saul (ed.).The Chemistry of Cyanates and Their Thio Derivatives. Vol. Part 1. Chichester: Wiley.ISBN0-471-99477-4.LCCN75-6913.
![The reaction of acetophenone enolate with phenyl isothiocyanate. In this one-pot synthesis[9] the ultimate reaction product is a Thiazolidine. This reaction is stereoselective with the formation of the Z-isomer only.](/mt/?noimg=&dark=on&url=https%3a%2f%2fen.wikipedia.org%2fwiki%2fFile%3aThiazolidineSynthesis.gif)
