Organic Sulfur Compounds 1961
DOI: 10.1016/b978-1-4831-9982-5.50030-0
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Thiocyanates, Thiocyanogen, and Related Compounds

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1964
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Cited by 25 publications
(7 citation statements)
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“…Reaction of (SCN)2 with sulfhydryls, phenols, and heterocyclic aromatic compounds has been described previously (Wood, 1946;Bacon, 1961). The SCN moiety of (SCN)2 is introduced, to give the sulfenyl thiocyanate derivative of sulfhydryls and the aryl thiocyanate derivatives of aromatic compounds.…”
Section: Discussionmentioning
confidence: 99%
“…Reaction of (SCN)2 with sulfhydryls, phenols, and heterocyclic aromatic compounds has been described previously (Wood, 1946;Bacon, 1961). The SCN moiety of (SCN)2 is introduced, to give the sulfenyl thiocyanate derivative of sulfhydryls and the aryl thiocyanate derivatives of aromatic compounds.…”
Section: Discussionmentioning
confidence: 99%
“…41; see also ref. 42). It was shown that the resulting protein sulfenyl thiocyanate (R-S-SCN) is in equilibrium with the sulfenic acid (R-S-OH) by hydrolysis and that this sulfenic acid can also react with another thiol to form a disulfide link.…”
mentioning
confidence: 99%
“…We have shown that H 2 NC(dO)SOreacts with CySH, first to give CySSC(dO)-NH 2 , and eventually with excess CySH to give CySSCy and H 2 NC(dO)S -. While a detailed mechanistic study of the reaction of OSCNwith CySH has not yet been carried out, it has been previously demonstrated that (SCN) 2 /HOSCN reacts with CySH to give the intermediate CySSCN (24) and that CySSCN subsequently reacts with CySH (13,16) and other thiols (12) The only characterized compounds that we are aware of that contain carbamoyl moieties are the trihalomethyl derivatives X 3 CSSC(dO)NH 2 (X ) F, Cl) (26)(27)(28). However, functionalized derivatives of the parent functional group are relatively common.…”
Section: Resultsmentioning
confidence: 99%
“…We have shown that H 2 NC(O)SO − reacts with CySH, first to give CySSC(O)NH 2 , and eventually with excess CySH to give CySSCy and H 2 NC(O)S − . While a detailed mechanistic study of the reaction of OSCN − with CySH has not yet been carried out, it has been previously demonstrated that (SCN) 2 /HOSCN reacts with CySH to give the intermediate CySSCN and that CySSCN subsequently reacts with CySH , and other thiols to give disulfides. Thus, OSCN − and H 2 NC(O)SO − exhibit analogous reaction chemistry with respect to CySH.…”
Section: Discussionmentioning
confidence: 99%