Thiol

In organic chemistry, a thiol (/ˈθaɪɒl/;^[1] from Ancient Greek θεῖον (theion) 'sulfur'^[2]), or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols (that is, sulfur takes the place of oxygen in the hydroxyl (−OH) group of an alcohol), and the word is a blend of "thio-" with "alcohol".

Many thiols have strong odors resembling that of garlic or rotten eggs. Thiols are used as odorants to assist in the detection of natural gas (which in pure form is odorless), and the "smell of natural gas" is due to the smell of the thiol used as the odorant. Thiols are sometimes referred to as mercaptans (/mərˈkæptæn/)^[3] or mercapto compounds,^[4]^[5]^[6] a term introduced in 1832 by William Christopher Zeise and is derived from the Latin mercurio captāns ('capturing mercury')^[7] because the thiolate group (RS⁻) bonds very strongly with mercury compounds.^[8]

^ Dictionary Reference: thiol Archived 2013-04-11 at the Wayback Machine
^ θεῖον Archived 2017-05-10 at the Wayback Machine, Henry George Liddell, Robert Scott, A Greek–English Lexicon
^ Dictionary Reference: mercaptan Archived 2012-11-13 at the Wayback Machine
^ Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 1. London: Wiley. doi:10.1002/9780470771310. ISBN 9780470771310.
^ Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 2. London: Wiley. doi:10.1002/9780470771327. ISBN 9780470771327.
^ R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. ISBN 978-0-471-95512-2.
^ Oxford American Dictionaries (Mac OS X Leopard).
^
See:
- Zeise, William Christopher (1834). "Mercaptanet, med bemaerkninger over nogle andre nye producter af svovelvinsyresaltene, som og af den tunge vinolie, ved sulfureter" [Mercaptan, with remarks on some other new products of salts of ethyl hydrogen sulfate as well as of heavy oil of wine, by means of hydrogen sulfide]. Kongelige Danske Videnskabers Selskabs Skrifter. 4th series (in Danish). 6: 1–70. On p. 13 the word "mercaptan" is coined.
- German translation: Zeise, W. C. (1834). "Das Mercaptan, nebst Bermerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl" [Mercaptan together with comments on some new products from the effect of hydrogen sulfide on salts of ethyl sulfate ((C₂H₅)HSO₄) and heavy oil of wine (a mixture of diethyl sulfate, diethyl sulfite, and polymerized ethylene)]. Annalen der Physik und Chemie. 2nd series (in German). 31 (24): 369–431. From p. 378: " … nenne ich den vom Quecksilber aufgenommenen Stoff Mercaptum (von: Corpus mercurio captum) … " ( … I name the substance [that is] absorbed by mercury "mercaptum" (from: the body (substance) [that] has been absorbed by mercury) … )
- German translation is reprinted in:Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige andere neue Erzeugnisse der Wirkung schwefelweinsaurer Salze, wie auch des schweren Weinöls auf Sulphurete". Journal für Praktische Chemie. 1 (1): 257–268, 345–356, 396–413, 457–475. doi:10.1002/prac.18340010154.
- Summarized in: Zeise, W. C. (1834). "Ueber das Mercaptan" [On mercaptan]. Annalen der Pharmacie. 11 (1): 1–10. doi:10.1002/jlac.18340110102. Archived from the original on 2015-03-20.
- Zeise, William Christopher (1834). "Sur le mercaptan; avec des observations sur d'autres produits resultant de l'action des sulfovinates ainsi que de l'huile de vin, sur des sulfures metalliques" [On mercaptan; with observations on other products resulting from the action of sulfovinates [typically, ethyl hydrogen sulfate] as well as oil of wine [a mixture of diethylsulfate and ethylene polymers] on metal sulfides]. Annales de Chimie et de Physique. 56: 87–97. Archived from the original on 2015-03-20. "Mercaptan" (ethyl thiol) was discovered in 1834 by the Danish professor of chemistry William Christopher Zeise (1789–1847). He called it "mercaptan", a contraction of "corpus mercurio captans" (mercury-capturing substance) [p. 88], because it reacted violently with mercury(II) oxide ("deutoxide de mercure") [p. 92].
- The article in Annales de Chimie et de Physique (1834) was translated from the German article: Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl". Annalen der Physik und Chemie. 107 (27): 369–431. Bibcode:1834AnP...107..369Z. doi:10.1002/andp.18341072402. Archived from the original on 2015-03-20.

[1] Dictionary Reference: thiol Archived 2013-04-11 at the Wayback Machine

[2] θεῖον Archived 2017-05-10 at the Wayback Machine, Henry George Liddell, Robert Scott, A Greek–English Lexicon

[3] Dictionary Reference: mercaptan Archived 2012-11-13 at the Wayback Machine

[Patai-4] Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 1. London: Wiley. doi:10.1002/9780470771310. ISBN 9780470771310.

[5] Patai, Saul, ed. (1974). The Chemistry of the Thiol Group. Part 2. London: Wiley. doi:10.1002/9780470771327. ISBN 9780470771327.

[CremlynAn-6] R. J. Cremlyn (1996). An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. ISBN 978-0-471-95512-2.

[ReferenceA-7] Oxford American Dictionaries (Mac OS X Leopard).

[8] See:
Zeise, William Christopher (1834). "Mercaptanet, med bemaerkninger over nogle andre nye producter af svovelvinsyresaltene, som og af den tunge vinolie, ved sulfureter" [Mercaptan, with remarks on some other new products of salts of ethyl hydrogen sulfate as well as of heavy oil of wine, by means of hydrogen sulfide]. Kongelige Danske Videnskabers Selskabs Skrifter. 4th series (in Danish). 6: 1–70. On p. 13 the word "mercaptan" is coined.

German translation: Zeise, W. C. (1834). "Das Mercaptan, nebst Bermerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl" [Mercaptan together with comments on some new products from the effect of hydrogen sulfide on salts of ethyl sulfate ((C₂H₅)HSO₄) and heavy oil of wine (a mixture of diethyl sulfate, diethyl sulfite, and polymerized ethylene)]. Annalen der Physik und Chemie. 2nd series (in German). 31 (24): 369–431. From p. 378: " … nenne ich den vom Quecksilber aufgenommenen Stoff Mercaptum (von: Corpus mercurio captum) … " ( … I name the substance [that is] absorbed by mercury "mercaptum" (from: the body (substance) [that] has been absorbed by mercury) … )

German translation is reprinted in:Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige andere neue Erzeugnisse der Wirkung schwefelweinsaurer Salze, wie auch des schweren Weinöls auf Sulphurete". Journal für Praktische Chemie. 1 (1): 257–268, 345–356, 396–413, 457–475. doi:10.1002/prac.18340010154.

Summarized in: Zeise, W. C. (1834). "Ueber das Mercaptan" [On mercaptan]. Annalen der Pharmacie. 11 (1): 1–10. doi:10.1002/jlac.18340110102. Archived from the original on 2015-03-20.

Zeise, William Christopher (1834). "Sur le mercaptan; avec des observations sur d'autres produits resultant de l'action des sulfovinates ainsi que de l'huile de vin, sur des sulfures metalliques" [On mercaptan; with observations on other products resulting from the action of sulfovinates [typically, ethyl hydrogen sulfate] as well as oil of wine [a mixture of diethylsulfate and ethylene polymers] on metal sulfides]. Annales de Chimie et de Physique. 56: 87–97. Archived from the original on 2015-03-20. "Mercaptan" (ethyl thiol) was discovered in 1834 by the Danish professor of chemistry William Christopher Zeise (1789–1847). He called it "mercaptan", a contraction of "corpus mercurio captans" (mercury-capturing substance) [p. 88], because it reacted violently with mercury(II) oxide ("deutoxide de mercure") [p. 92].

The article in Annales de Chimie et de Physique (1834) was translated from the German article: Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl". Annalen der Physik und Chemie. 107 (27): 369–431. Bibcode:1834AnP...107..369Z. doi:10.1002/andp.18341072402. Archived from the original on 2015-03-20.

[9] Zeise, William Christopher (1834). "Mercaptanet, med bemaerkninger over nogle andre nye producter af svovelvinsyresaltene, som og af den tunge vinolie, ved sulfureter" [Mercaptan, with remarks on some other new products of salts of ethyl hydrogen sulfate as well as of heavy oil of wine, by means of hydrogen sulfide]. Kongelige Danske Videnskabers Selskabs Skrifter. 4th series (in Danish). 6: 1–70. On p. 13 the word "mercaptan" is coined.

[10] German translation: Zeise, W. C. (1834). "Das Mercaptan, nebst Bermerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl" [Mercaptan together with comments on some new products from the effect of hydrogen sulfide on salts of ethyl sulfate ((C₂H₅)HSO₄) and heavy oil of wine (a mixture of diethyl sulfate, diethyl sulfite, and polymerized ethylene)]. Annalen der Physik und Chemie. 2nd series (in German). 31 (24): 369–431. From p. 378: " … nenne ich den vom Quecksilber aufgenommenen Stoff Mercaptum (von: Corpus mercurio captum) … " ( … I name the substance [that is] absorbed by mercury "mercaptum" (from: the body (substance) [that] has been absorbed by mercury) … )

[11] German translation is reprinted in:Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige andere neue Erzeugnisse der Wirkung schwefelweinsaurer Salze, wie auch des schweren Weinöls auf Sulphurete". Journal für Praktische Chemie. 1 (1): 257–268, 345–356, 396–413, 457–475. doi:10.1002/prac.18340010154.

[12] Summarized in: Zeise, W. C. (1834). "Ueber das Mercaptan" [On mercaptan]. Annalen der Pharmacie. 11 (1): 1–10. doi:10.1002/jlac.18340110102. Archived from the original on 2015-03-20.

[13] Zeise, William Christopher (1834). "Sur le mercaptan; avec des observations sur d'autres produits resultant de l'action des sulfovinates ainsi que de l'huile de vin, sur des sulfures metalliques" [On mercaptan; with observations on other products resulting from the action of sulfovinates [typically, ethyl hydrogen sulfate] as well as oil of wine [a mixture of diethylsulfate and ethylene polymers] on metal sulfides]. Annales de Chimie et de Physique. 56: 87–97. Archived from the original on 2015-03-20. "Mercaptan" (ethyl thiol) was discovered in 1834 by the Danish professor of chemistry William Christopher Zeise (1789–1847). He called it "mercaptan", a contraction of "corpus mercurio captans" (mercury-capturing substance) [p. 88], because it reacted violently with mercury(II) oxide ("deutoxide de mercure") [p. 92].

[14] The article in Annales de Chimie et de Physique (1834) was translated from the German article: Zeise, W. C. (1834). "Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl". Annalen der Physik und Chemie. 107 (27): 369–431. Bibcode:1834AnP...107..369Z. doi:10.1002/andp.18341072402. Archived from the original on 2015-03-20.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]