31:
1042:
1454:, 2-mercaptoethyl sulfonic acid. Thiolates, the conjugate bases derived from thiols, form strong complexes with many metal ions, especially those classified as soft. The stability of metal thiolates parallels that of the corresponding sulfide minerals.
1187:, sulfur is a relatively soft (polarizable) atom. This explains the tendency of thiols to bind to soft elements and ions such as mercury, lead, or cadmium. The stability of metal thiolates parallels that of the corresponding sulfide minerals.
1304:
1434:(non-protein-based helper molecules) feature thiols. The biosynthesis and degradation of fatty acids and related long-chain hydrocarbons is conducted on a scaffold that anchors the growing chain through a thioester derived from the thiol
815:
The thiourea route works well with primary halides, especially activated ones. Secondary and tertiary thiols are less easily prepared. Secondary thiols can be prepared from the ketone via the corresponding
443:
has been shown to be required by a specific mouse olfactory receptor, MOR244-3, which is highly responsive to MTMT as well as to various other thiols and related compounds. A human olfactory receptor,
2801:
Kazem-Rostami, Masoud; Khazaei, Ardeshir; Moosavi-Zare, Ahmad; Bayat, Mohammad; Saednia, Shahnaz (2012). "Novel One-Pot
Synthesis of Thiophenols from Related Triazenes under Mild Conditions".
2059:(1789–1847). He called it "mercaptan", a contraction of "corpus mercurio captans" (mercury-capturing substance) , because it reacted violently with mercury(II) oxide ("deutoxide de mercure") .
959:
respectively. Thiols and alcohols are also very different in their reactivity, thiols being more easily oxidized than alcohols. Thiolates are more potent nucleophiles than the corresponding
2972:
Stubbe, JoAnne; Nocera, Daniel G.; Yee, Cyril S.; Chang, Michelle C. Y. (2003). "Radical
Initiation in the Class I Ribonucleotide Reductase: Long-Range Proton-Coupled Electron Transfer?".
1327:, the thiol group plays a very important role in biology. When the thiol groups of two cysteine residues (as in monomers or constituent units) are brought near each other in the course of
1466:
consists mainly of low-molecular-weight thiols and derivatives with a foul odor, which protects the skunk from predators. Owls are able to prey on skunks, as they lack a sense of smell.
2523:
1757:
2939:
1355:
of multi-unit proteins by forming fairly strong covalent bonds between different peptide chains. A physical manifestation of cysteine-cystine equilibrium is provided by
271:– are about 40 picometers longer than typical C−O bonds. The C−S−H angles approach 90° whereas the angle for the C−O−H group is more obtuse. In solids and liquids, the
403:
consists mainly of low-molecular-weight thiols and derivatives. These compounds are detectable by the human nose at concentrations of only 10 parts per billion. Human
2923:
2039:"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"
1924:[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].
1393:. Cysteine residues may also react with heavy metal ions (Zn, Cd, Pb, Hg, Ag) because of the high affinity between the soft sulfide and the soft metal (see
527:, in 1937. Many gas distributors were odorizing gas prior to this event. Most currently-used gas odorants contain mixtures of mercaptans and sulfides, with
3266:
3172:
168:(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
1984:"Das Mercaptan, nebst Bemerkungen über einige andere neue Erzeugnisse der Wirkung schwefelweinsaurer Salze, wie auch des schweren Weinöls auf Sulphurete"
542:(LPG, propane). In situations where thiols are used in commercial industry, such as liquid petroleum gas tankers and bulk handling systems, an oxidizing
4185:
2243:
Andersen K. K.; Bernstein D. T.; Caret R. L.; Romanczyk L. J., Jr. (1982). "Chemical
Constituents of the Defensive Secretion of the Striped Skunk (
709:
Such reactions are conducted in the presence of acidic catalysts. The other principal route to thiols involves the addition of hydrogen sulfide to
4190:
2041:[On mercaptan; with observations on other products resulting from the action of sulfovinates as well as oil of wine on metal sulfides].
1252:. They arise from or can be generated by a number of routes, but the principal method is H-atom abstraction from thiols. Another method involves
2515:
574:
have similar solubility characteristics and boiling points, whereas the same is not true of alcohols and their corresponding isomeric ethers.
3073:
2140:
1941:"Das Mercaptan, nebst Bermerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl"
1882:
3209:
Applications, Properties, and
Synthesis of ω-Functionalized n-Alkanethiols and Disulfides – the Building Blocks of Self-Assembled Monolayers
2070:"Das Mercaptan, nebst Bemerkungen über einige neue Producte aus der Einwirkung der Sulfurete auf weinschwefelsaure Salze und auf das Weinöl"
3219:
2867:
M. E. Alonso; H. Aragona (1978). "Sulfide
Synthesis in Preparation of Unsymmetrical Dialkyl Disulfides: Sec-butyl Isopropyl Disulfide".
2097:
546:
is used to destroy the odor. A copper-based oxidation catalyst neutralizes the volatile thiols and transforms them into inert products.
3234:
2050:
2956:
2029:
1256:
of organic disulfides. In biology thiyl radicals are responsible for the formation of the deoxyribonucleic acids, building blocks for
2330:
2153:
1922:"Mercaptanet, med bemaerkninger over nogle andre nye producter af svovelvinsyresaltene, som og af den tunge vinolie, ved sulfureter"
1854:
1821:
1669:
1165:
2584:
3080:
Sulfhydryls are scavengers of free radicals, protecting chemical damage induced by either ionizing radiation or alkylating agents.
1754:
3056:
Koch, Cameron J.; Parliament, Matthew B.; Brown, J. Martin; Urtasun, Raul C. (2010). "Chemical
Modifiers of Radiation Response".
2113:
2405:
Lin, Dayu; Zhang, Shaozhong; Block, Eric; Katz, Lawrence C. (2005). "Encoding social signals in the mouse main olfactory bulb".
4223:
3259:
1785:
991:
Thiols are easily deprotonated. Relative to the alcohols, thiols are more acidic. The conjugate base of a thiol is called a
1943:[Mercaptan together with comments on some new products from the effect of hydrogen sulfide on salts of ethyl sulfate ((C
2456:
Duan, Xufang; Block, Eric; Li, Zhen; Connelly, Timothy; Zhang, Jian; Huang, Zhimin; Su, Xubo; Pan, Yi; et al. (2012).
2274:
Wood W. F.; Sollers B. G.; Dragoo G. A.; Dragoo J. W. (2002). "Volatile
Components in Defensive Spray of the Hooded Skunk,
4089:
3208:
1739:
1394:
2895:
1977:( … I name the substance absorbed by mercury "mercaptum" (from: the body (substance) has been absorbed by mercury) … )
570:
than alcohols of similar molecular weight. For this reason also, thiols and their corresponding sulfide functional group
3201:
1921:
520:
504:. The effect of the latter compound is present only at low concentrations. The pure mercaptan has an unpleasant odor.
4218:
3662:
3252:
2117:
1664:
614:
Volatile thiols are easily and almost unerringly detected by their distinctive odor. Sulfur-specific analyzers for
2894:
Akhmadullina, A. G.; Kizhaev, B. V.; Nurgalieva, G. M.; Khrushcheva, I. K.; Shabaeva, A. S.; et al. (1993).
2326:
2056:
1940:
1692:
276:
215:
3164:
399:. The odors of thiols, particularly those of low molecular weight, are often strong and repulsive. The spray of
3699:
1712:
1375:
1308:
1261:
283:
1983:
760:
efficient owing to the competing formation of sulfides. Instead, alkyl halides are converted to thiols via an
447:, has been identified which, in the presence of copper, is highly responsive to the gas odorants (see below)
4172:
1679:
1600:
1431:
539:
4072:
1659:
1268:, an antioxidant in biology. Thiyl radicals (sulfur-centred) can transform to carbon-centred radicals via
901:
Thiols are prepared by reductive dealkylation of sulfides, especially benzyl derivatives and thioacetals.
876:
654:
485:
423:
SH; MTMT) is a strong-smelling volatile thiol, also detectable at parts per billion levels, found in male
80:
1419:
4179:
4067:
1955:) and heavy oil of wine (a mixture of diethyl sulfate, diethyl sulfite, and polymerized ethylene)].
1398:
1288:
1253:
1020:
263:. Thiols and alcohols have similar connectivity. Because sulfur atoms are larger than oxygen atoms, C−S
99:
2169:
Andersen K. K.; Bernstein D. T. (1978). "Some
Chemical Constituents of the Scent of the Striped Skunk (
305:
of sulfur and hydrogen. In contrast, O−H bonds in hydroxyl groups are more polar. Thiols have a lower
4148:
3593:
2469:
2414:
2217:
2081:
1654:
1555:
1352:
1273:
658:
493:
3454:
1572:
1083:
769:
721:
326:
134:
30:
3225:
2915:
2818:
2438:
2303:
2190:
1356:
1344:
1038:
of 2.68. Thus, thiolates can be obtained from thiols by treatment with alkali metal hydroxides.
662:
306:
717:
displacement, using the suitable organic halide and sodium hydrogen sulfide has also been used.
4138:
4108:
3866:
3488:
3146:
3101:
3069:
3038:
2989:
2952:
2837:
2779:
2747:
2719:
2691:
2632:
2497:
2430:
2387:
2295:
2149:
2069:
1878:
1850:
1817:
1674:
1630:
1387:
1237:
1180:
1087:
825:
741:
737:
615:
571:
524:
302:
298:
236:
46:
2038:
3843:
3337:
3275:
3231:
3136:
3128:
3093:
3061:
3028:
3020:
2981:
2944:
2907:
2876:
2849:
2810:
2667:
2614:
2610:
2487:
2477:
2422:
2377:
2369:
2287:
2256:
2225:
2182:
2089:
2021:
2009:
1995:
1904:
1842:
1809:
1707:
1649:
1639:
1407:
1371:
1196:
880:
820:. A related two-step process involves alkylation of thiosulfate to give the thiosulfonate ("
674:
428:
272:
175:
118:
56:
4213:
4062:
3821:
3816:
3799:
3782:
3583:
3332:
3238:
2208:
Andersen K. K., Bernstein D. T.; Bernstein (1978). "1-Butanethiol and the
Striped Skunk".
1789:
1761:
1743:
1620:
1605:
1527:
1415:
1390:
1383:
528:
459:
452:
2322:
415:)-3-methyl-3-mercapto-1-ol (MSH), detectable at 2 parts per billion and having a fruity,
2576:
2473:
2418:
2221:
2085:
974:
Thiols, or more specific their conjugate bases, are readily alkylated to give sulfides:
713:. Such reactions are usually conducted in the presence of an acid catalyst or UV light.
4133:
4128:
4004:
3999:
3994:
3787:
3754:
3538:
3520:
3510:
3141:
3116:
3065:
3033:
3008:
2492:
2457:
2382:
2353:
1777:
1731:
1635:
1514:
1340:
1041:
753:
374:
2560:
Luo, Y.-R.; Cheng, J.-P. (2017). "Bond
Dissociation Energies". In J. R. Rumble (ed.).
2055:"Mercaptan" (ethyl thiol) was discovered in 1834 by the Danish professor of chemistry
1311:, demonstrating the role of thiyl radicals in producing the genetic machinery of life.
4207:
4153:
4101:
4032:
3918:
3908:
3903:
3893:
3888:
3838:
3833:
3749:
3744:
3734:
3588:
3543:
3505:
3493:
3464:
3342:
3196:
2822:
2260:
1233:
1224:
1091:
908:-arylation or the replacement of diazonium leaving group with sulfhydryl anion (SH):
603:
559:
555:
432:
3094:
2919:
2307:
4084:
3971:
3966:
3943:
3694:
3533:
3459:
3396:
3391:
3369:
3325:
3310:
3300:
3214:
2194:
1782:
1500:
1476:
1439:
1292:
1241:
1229:
1200:
682:
642:-active but signals for divalent sulfur are very broad and of little utility). The
478:
339:
2442:
4143:
4096:
4057:
3938:
3826:
3811:
3806:
3794:
3359:
3354:
3320:
3315:
3305:
3283:
2770:
2742:
2714:
2686:
2627:
1615:
1541:
1486:
1447:
1363:
1265:
1184:
650:
619:
535:
516:
512:
508:
448:
264:
165:
111:
2358:(Common Skunk), with Remarks on the Physiological Properties of This Secretion"
1736:
282:
The S−H bond is much weaker than the O−H bond as reflected in their respective
4052:
4043:
3923:
3878:
3774:
3739:
3729:
3669:
3605:
3528:
3476:
2291:
1702:
1610:
1586:
1451:
1435:
1321:
940:
821:
631:
501:
474:
252:
2948:
2880:
2853:
2769:
Eliel, Ernest L.; Lynch, Joseph E.; Kume, Fumitaka; Frye, Stephen V. (1993).
2671:
2093:
2025:
1999:
4019:
3933:
3898:
3883:
3871:
3714:
3689:
3498:
3211:
by D. Witt, R. Klajn, P. Barski, B.A. Grzybowski at Northwestern University.
2482:
2145:
1411:
1379:
1332:
1067:
944:
817:
635:
582:
The S−H bond in thiols is weak compared to the O−H bond in alcohols. For CH
543:
435:, activating certain mouse olfactory sensory neurons, and attracting female
268:
3150:
3132:
3042:
2993:
2814:
2501:
2434:
2391:
2299:
1846:
1813:
1303:
824:"), followed by hydrolysis. The method is illustrated by one synthesis of
481:
and the "skunky" odor of beer that has been exposed to ultraviolet light.
4027:
3981:
3948:
3644:
3550:
3424:
3379:
3364:
2896:"Heterogeneous catalytic demercaptization of light hydrocarbon feedstock"
1697:
1625:
1324:
1269:
960:
765:
678:
558:, both with water molecules and among themselves. Hence, they have lower
467:
161:
142:
17:
2426:
2373:
1264:(see figure). Thiyl intermediates also are produced by the oxidation of
3989:
3913:
3764:
3759:
3724:
3709:
3704:
3674:
3657:
3481:
3408:
3374:
2911:
2186:
1443:
1397:). This can deform and inactivate the protein, and is one mechanism of
1348:
1336:
1328:
1122:
Oxidation can also be effected by oxygen in the presence of catalysts:
1059:
936:
894:
Phenols can be converted to the thiophenols via rearrangement of their
883:
react with sulfur to give the thiolates, which are readily hydrolyzed:
768:. This multistep, one-pot process proceeds via the intermediacy of the
714:
567:
563:
497:
325:
is added to the name of the alkane. This method is nearly identical to
275:
between individual thiol groups is weak, the main cohesive force being
3024:
3009:"Hydrogen Exchange Equilibria in Glutathione Radicals: Rate Constants"
2985:
2229:
1179:(capturing mercury) because the thiolate group bonds so strongly with
752:
In general, on the typical laboratory scale, the direct reaction of a
4077:
4009:
3853:
3562:
3555:
3449:
3430:
3419:
3403:
3349:
1643:
1463:
1367:
1281:
1277:
1244:. They have the formula RS where R is an organic substituent such as
1063:
1016:
956:
952:
948:
710:
489:
463:
444:
440:
396:
157:
138:
91:
3244:
2771:"Chiral 1,3-oxathiane from (+)-Pulegone: Hexahydro-4,4,7-trimethyl-4
2458:"Crucial role of copper in detection of metal-coordinating odorants"
1280:-centred radicals could lead to protein damage via the formation of
2840:[A new method for the preparation of aromatic mercaptans].
3958:
3928:
3719:
3684:
3679:
3652:
3600:
3567:
3471:
3295:
1302:
1245:
1173:
1055:
1040:
436:
424:
416:
404:
400:
330:
248:
219:
107:
29:
3386:
3100:(Ninth ed.). New York: Pearson Benjamin Cummings. pp.
3007:
Hofstetter, Dustin; Nauser, Thomas; Koppenol, Willem H. (2010).
1287:
Because of the weakness of the S−H bond, thiols can function as
1249:
392:
290:
S−H, the BDE is 366 kJ/mol (87 kcal/mol), while for CH
3248:
1257:
1006:
996:
639:
181:
62:
2937:
Roy, Kathrin-Maria (2005). "Thiols and Organic Sulphides".
2838:"Eine neue Methode zur Darstellung aromatischer Mercaptane"
1386:. Active site cysteine residues are the functional unit in
602:
for X = O. Hydrogen-atom abstraction from a thiol gives a
354:
in the name of the equivalent alcohol compound. Example: CH
65:
2654:
Urquhart, G. G.; Gates, J. W. Jr.; Connor, Ralph (1941). "
2516:"Copper key to our sensitivity to rotten eggs' foul smell"
681:. This method is employed for the industrial synthesis of
68:
2354:"A Chemical Study of the Secretion of the Anal Glands of
673:
In industry, methanethiol is prepared by the reaction of
199:
190:
1054:
Thiols, especially in the presence of base, are readily
458:
as well as other low molecular weight thiols, including
279:
between the highly polarizable divalent sulfur centers.
1343:(−S−S−). Disulfide bonds can contribute to a protein's
1967:" … nenne ich den vom Quecksilber aufgenommenen Stoff
500:
thiol, is responsible for the characteristic scent of
3117:"Myeloperoxidase: a target for new drug development?"
1164:
With metal ions, thiolates behave as ligands to form
511:
distributors were required to add thiols, originally
294:
O−H, the BDE is 440 kJ/mol (110 kcal/mol).
202:
187:
477:
caused by an unintended reaction between sulfur and
196:
193:
149:) group of an alcohol), and the word is a blend of "
71:
4121:
4041:
4018:
3980:
3957:
3852:
3773:
3643:
3620:
3576:
3519:
3442:
3417:
3282:
2687:"Mecaptans from Thioketals: Cyclododecyl Mercaptan"
484:Not all thiols have unpleasant odors. For example,
184:
178:
59:
3058:Leibel and Phillips Textbook of Radiation Oncology
27:Any organic compound having a sulfanyl group (–SH)
2741:Melvin S. Newman and Frederick W. Hetzel (1990).
156:Many thiols have strong odors resembling that of
1148:Thiols participate in thiol-disulfide exchange:
534:as the main odor constituent in natural gas and
431:and co-workers showed that MTMT functioned as a
317:There are several ways to name the alkylthiols:
3228:, by Columbia Gas of Pennsylvania and Maryland.
2607:Kirk-Othmer Encyclopedia of Chemical Technology
2547:Kirk-Othmer Encyclopedia of Chemical Technology
2066:(1834) was translated from the German article:
1926:Kongelige Danske Videnskabers Selskabs Skrifter
1450:on Earth, arises from the reaction mediated by
1236:, are commonly invoked to explain reactions in
935:Akin to the chemistry of alcohols, thiols form
519:(which is naturally odorless) after the deadly
466:breath, and the strong-smelling cyclic sulfide
2940:Ullmann's Encyclopedia of Industrial Chemistry
2743:"Thiophenols from Phenols: 2-Naphthalenethiol"
606:with the formula RS, where R = alkyl or aryl.
247:Thiols having the structure R−SH, in which an
3260:
618:are useful. Spectroscopic indicators are the
8:
1896:
1894:
1082:Oxidation by more powerful reagents such as
1005:of 10.5 vs 15 for butanol. Thiophenol has a
1868:
1866:
473:Thiols are also responsible for a class of
419:-like odor. (Methylthio)methanethiol (MeSCH
222:
3640:
3439:
3267:
3253:
3245:
2900:Chemistry and Technology of Fuels and Oils
1045:Synthesis of thiophenolate from thiophenol
772:, which is hydrolyzed in a separate step:
736:This method is used for the production of
309:relative to their corresponding alcohols.
3140:
3032:
2491:
2481:
2381:
1994:(1): 257–268, 345–356, 396–413, 457–475.
1875:An Introduction to Organosulfur Chemistry
720:Another method entails the alkylation of
1934:On p. 13 the word "mercaptan" is coined.
1839:The Chemistry of the Thiol Group. Part 2
1806:The Chemistry of the Thiol Group. Part 1
358:SH would be methyl mercaptan, just as CH
2685:S. R. Wilson, G. M. Georgiadis (1990).
2615:10.1002/0471238961.2008091518150205.a01
1799:
1797:
1723:
301:because of the small difference in the
1764:, Henry George Liddell, Robert Scott,
1347:if the cysteines are part of the same
1156:This reaction is important in nature.
649:band appears near 2400 cm in the
3165:"Understanding Owls – The Owls Trust"
2141:CRC Handbook of Chemistry and Physics
7:
3232:What Is the Worst Smelling Chemical?
3220:The Columbia Electronic Encyclopedia
3175:from the original on 5 February 2018
2333:from the original on October 8, 2010
1284:−C bonds or backbone fragmentation.
488:contributes to the aroma of roasted
137:(that is, sulfur takes the place of
133:. Thiols are the sulfur analogue of
2587:from the original on 23 August 2017
2037:Zeise, William Christopher (1834).
1980:German translation is reprinted in:
1920:Zeise, William Christopher (1834).
1877:. Chichester: John Wiley and Sons.
1166:transition metal thiolate complexes
160:or rotten eggs. Thiols are used as
3066:10.1016/b978-1-4160-5897-7.00004-4
2713:E. Jones and I. M. Moodie (1990).
1378:as well, contributing to covalent
1260:. This conversion is catalysed by
554:Thiols show little association by
227:('capturing mercury') because the
121:itself is referred to as either a
25:
3092:Reece, Urry; et al. (2011).
2562:Handbook of Chemistry and Physics
2144:(87th ed.). Boca Raton, FL:
1670:3-Mercapto-1-propanesulfonic acid
1185:hard/soft acid/base (HSAB) theory
2926:from the original on 2011-08-15.
2526:from the original on 10 May 2017
2100:from the original on 2015-03-20.
2064:Annales de Chimie et de Physique
2053:from the original on 2015-03-20.
2043:Annales de Chimie et de Physique
2032:from the original on 2015-03-20.
1232:derived from mercaptans, called
1152:RS−SR + 2 R′SH → 2 RSH + R′S−SR′
174:
55:
3121:British Journal of Pharmacology
1320:As the functional group of the
657:, free thiol groups react with
255:group (SH), are referred to as
214:, a term introduced in 1832 by
2609:, 1997, Wiley-VCH, Weinheim.
164:to assist in the detection of
1:
2842:Journal für Praktische Chemie
2605:John S Roberts, "Thiols", in
2210:Journal of Chemical Education
2074:Annalen der Physik und Chemie
1988:Journal für Praktische Chemie
1957:Annalen der Physik und Chemie
1395:hard and soft acids and bases
898:-aryl dialkylthiocarbamates.
586:X−H, the bond enthalpies are
550:Boiling points and solubility
3202:The Periodic Table of Videos
3060:. Elsevier. pp. 55–68.
2545:Roberts, J. S., ed. (1997).
2462:Proc. Natl. Acad. Sci. U.S.A
2261:10.1016/0040-4020(82)80046-X
2138:Lide, David R., ed. (2006).
1901:Oxford American Dictionaries
1405:Drugs containing thiol group
1351:chain, or contribute to the
904:Thiophenols are produced by
756:with sodium hydrosulfide is
362:OH is called methyl alcohol.
2280:Journal of Chemical Ecology
2175:Journal of Chemical Ecology
1019:. A highly acidic thiol is
521:New London School explosion
251:group (R) is attached to a
235:) bonds very strongly with
4240:
3205:(University of Nottingham)
2844:. 2nd series (in German).
2789:, vol. 8, p. 302
2757:, vol. 6, p. 824
2729:, vol. 6, p. 979
2701:, vol. 7, p. 124
2642:, vol. 4, p. 401
2577:"Sulfur-33 NMR references"
2323:"Chemistry of Skunk Spray"
2118:Royal Society of Chemistry
1959:. 2nd series (in German).
1928:. 4th series (in Danish).
1665:3-Mercaptopropane-1,2-diol
1222:
978:RSH + R′Br + B → RSR′ + Br
373:is used as a prefix, e.g.
297:An S−H bond is moderately
284:bond dissociation energies
277:Van der Waals interactions
4162:
2836:Leuckart, Rudolf (1890).
2327:Humboldt State University
2057:William Christopher Zeise
1837:Patai, Saul, ed. (1974).
1804:Patai, Saul, ed. (1974).
1693:Doctor sweetening process
1362:Sulfhydryl groups in the
947:, which are analogous to
216:William Christopher Zeise
2949:10.1002/14356007.a26_767
2881:10.15227/orgsyn.058.0147
2854:10.1002/prac.18900410114
2672:10.15227/orgsyn.021.0036
2626:Speziale, A. J. (1963).
2094:10.1002/andp.18341072402
2026:10.1002/jlac.18340110102
2012:[On mercaptan].
2000:10.1002/prac.18340010154
1713:Thiol-disulfide exchange
1309:ribonucleotide reductase
1307:The catalytic cycle for
1262:ribonucleotide reductase
1183:compounds. According to
391:Many thiols have strong
218:and is derived from the
106:, where R represents an
4173:chemical classification
2943:. Weinheim: Wiley-VCH.
2483:10.1073/pnas.1111297109
2292:10.1023/A:1020573404341
1766:A Greek–English Lexicon
1680:Pentachlorobenzenethiol
1601:Dimercaptosuccinic acid
1462:The defensive spray of
890:RSLi + HCl → RSH + LiCl
877:Organolithium compounds
540:liquefied petroleum gas
267:– typically around 180
4224:Organosulfur compounds
3197:Mercaptans (or Thiols)
3133:10.1038/sj.bjp.0707358
2815:10.1055/s-0032-1316557
2549:. Weinheim: Wiley-VCH.
2352:Aldrich, T.B. (1896).
2325:. Dept. of Chemistry,
1973:Corpus mercurio captum
1873:R. J. Cremlyn (1996).
1660:Furan-2-ylmethanethiol
1312:
1160:Metal ion complexation
1078:→ R−S−S−R + 2 HBr
1046:
665:to give a red colour.
655:nitroprusside reaction
507:In the United States,
486:furan-2-ylmethanethiol
223:
42:
39: blue highlighted
4180:chemical nomenclature
3241:, by About Chemistry.
2658:-Dodecyl Mercaptan".
2068:Zeise, W. C. (1834).
2014:Annalen der Pharmacie
2010:"Ueber das Mercaptan"
2008:Zeise, W. C. (1834).
1982:Zeise, W. C. (1834).
1939:Zeise, W. C. (1834).
1937:German translation:
1847:10.1002/9780470771327
1814:10.1002/9780470771310
1530: – CH
1399:heavy metal poisoning
1306:
1299:Biological importance
1195:Thiolates react with
1044:
1021:pentafluorothiophenol
728:RX + NaSH → RSH + NaX
243:Structure and bonding
100:organosulfur compound
33:
1778:Dictionary Reference
1732:Dictionary Reference
1655:Grapefruit mercaptan
1353:quaternary structure
1316:Cysteine and cystine
1172:is derived from the
1058:by reagents such as
1015:of 6, versus 10 for
995:. Butanethiol has a
659:sodium nitroprusside
494:grapefruit mercaptan
3636:not C, H or O)
2474:2012PNAS..109.3492D
2427:10.1038/nature03414
2419:2005Natur.434..470L
2374:10.1084/jem.1.2.323
2222:1978JChEd..55..159A
2086:1834AnP...107..369Z
1420:Sodium aurothiolate
1414:(antihypertensive)
1276:. The formation of
1084:sodium hypochlorite
1066:to give an organic
770:isothiouronium salt
722:sodium hydrosulfide
566:in water and other
395:resembling that of
382:Physical properties
329:and is used by the
4078:Hypervalent iodine
3237:2011-06-06 at the
3226:What is Mercaptan?
3013:Chem. Res. Toxicol
2912:10.1007/bf00728009
2775:-1,3-benzoxathiin"
2715:"2-Thiophenethiol"
2581:www.pascal-man.com
2520:chemistryworld.com
2356:Mephitis mephitiga
2187:10.1007/BF00988589
1788:2012-11-13 at the
1760:2017-05-10 at the
1742:2013-04-11 at the
1470:Examples of thiols
1380:catalytic activity
1374:with the enzyme's
1357:hair straightening
1345:tertiary structure
1333:oxidation reaction
1313:
1047:
748:Laboratory methods
663:ammonium hydroxide
616:gas chromatographs
212:mercapto compounds
153:" with "alcohol".
43:
4219:Functional groups
4201:
4200:
4139:Sulfenyl chloride
4117:
4116:
3616:
3615:
3435:(only C, H and O)
3276:Functional groups
3115:Malle, E (2007).
3075:978-1-4160-5897-7
3025:10.1021/tx100185k
3019:(10): 1596–1600.
2986:10.1021/cr020421u
2809:(13): 1893–1896.
2787:Collected Volumes
2780:Organic Syntheses
2755:Collected Volumes
2748:Organic Syntheses
2727:Collected Volumes
2720:Organic Syntheses
2699:Collected Volumes
2692:Organic Syntheses
2640:Collected Volumes
2633:Organic Syntheses
2413:(7032): 470–477.
2321:William F. Wood.
2276:Mephitis macroura
2255:(13): 1965–1970.
2245:Mephitis mephitis
2230:10.1021/ed055p159
2171:Mephitis mephitis
1884:978-0-471-95512-2
1841:. London: Wiley.
1808:. London: Wiley.
1675:1-Hexadecanethiol
1631:2-Mercaptoethanol
1388:cysteine protease
1372:noncovalent bonds
1238:organic chemistry
1177:mercurium captans
1088:hydrogen peroxide
881:Grignard reagents
826:thioglycolic acid
742:chloroacetic acid
738:thioglycolic acid
600:3.0 kcal/mol
592:2.1 kcal/mol
525:New London, Texas
327:naming an alcohol
303:electronegativity
110:or other organic
47:organic chemistry
41:sulfhydryl group.
16:(Redirected from
4231:
4168:
4073:Trifluoromethoxy
3641:
3637:
3440:
3436:
3289:
3269:
3262:
3255:
3246:
3185:
3184:
3182:
3180:
3169:theowlstrust.org
3161:
3155:
3154:
3144:
3112:
3106:
3105:
3099:
3096:Campbell Biology
3089:
3083:
3082:
3053:
3047:
3046:
3036:
3004:
2998:
2997:
2980:(6): 2167–2202.
2969:
2963:
2962:
2934:
2928:
2927:
2891:
2885:
2884:
2864:
2858:
2857:
2833:
2827:
2826:
2798:
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2617:
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2557:
2551:
2550:
2542:
2536:
2535:
2533:
2531:
2512:
2506:
2505:
2495:
2485:
2468:(9): 3492–3497.
2453:
2447:
2446:
2402:
2396:
2395:
2385:
2349:
2343:
2342:
2340:
2338:
2318:
2312:
2311:
2271:
2265:
2264:
2240:
2234:
2233:
2205:
2199:
2198:
2166:
2160:
2159:
2135:
2129:
2128:
2126:
2124:
2110:
2104:
2101:
2054:
2033:
2003:
1964:
1933:
1914:
1908:
1905:Mac OS X Leopard
1898:
1889:
1888:
1870:
1861:
1860:
1834:
1828:
1827:
1801:
1792:
1774:
1768:
1752:
1746:
1728:
1708:Saville reaction
1650:2-Mercaptoindole
1640:dithioerythritol
1559:-Butyl mercaptan
1446:, the principal
1422:(antiarthritic)
1418:(antiarthritic)
1408:6-Mercaptopurine
1391:catalytic triads
1384:catalytic triads
1214:
1213:
1212:
1197:carbon disulfide
1135:
1134:
1130:
1074:2 R−SH + Br
981:
922:
921:
920:
731:
675:hydrogen sulfide
610:Characterization
601:
599:
593:
591:
556:hydrogen bonding
532:-butyl mercaptan
456:-butyl mercaptan
429:Lawrence C. Katz
273:hydrogen-bonding
234:
226:
224:mercurio captāns
209:
208:
205:
204:
201:
198:
195:
192:
189:
186:
183:
180:
148:
127:sulfhydryl group
119:functional group
117:
105:
96:thiol derivative
78:
77:
74:
73:
70:
67:
64:
61:
40:
38:
21:
4239:
4238:
4234:
4233:
4232:
4230:
4229:
4228:
4204:
4203:
4202:
4197:
4166:
4158:
4113:
4068:Trichloromethyl
4063:Trifluoromethyl
4037:
4014:
3976:
3953:
3848:
3817:Phosphine oxide
3769:
3635:
3633:
3632:
3630:
3628:
3626:
3624:
3622:
3612:
3572:
3515:
3434:
3433:
3428:
3423:
3413:
3287:
3286:
3278:
3273:
3239:Wayback Machine
3193:
3188:
3178:
3176:
3163:
3162:
3158:
3114:
3113:
3109:
3091:
3090:
3086:
3076:
3055:
3054:
3050:
3006:
3005:
3001:
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2970:
2966:
2959:
2936:
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2931:
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2835:
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2800:
2799:
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2740:
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2725:
2712:
2711:
2707:
2697:
2684:
2683:
2679:
2653:
2652:
2648:
2638:
2628:"Ethanedithiol"
2625:
2624:
2620:
2604:
2600:
2590:
2588:
2575:Man, Pascal P.
2574:
2573:
2569:
2559:
2558:
2554:
2544:
2543:
2539:
2529:
2527:
2514:
2513:
2509:
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2404:
2403:
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2351:
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2320:
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2315:
2273:
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2268:
2242:
2241:
2237:
2207:
2206:
2202:
2168:
2167:
2163:
2156:
2137:
2136:
2132:
2122:
2120:
2112:
2111:
2107:
2080:(27): 369–431.
2067:
2062:The article in
2036:
2007:
2006:Summarized in:
1981:
1954:
1950:
1946:
1938:
1919:
1915:
1911:
1899:
1892:
1885:
1872:
1871:
1864:
1857:
1836:
1835:
1831:
1824:
1803:
1802:
1795:
1790:Wayback Machine
1775:
1771:
1762:Wayback Machine
1753:
1749:
1744:Wayback Machine
1729:
1725:
1721:
1689:
1684:
1621:Metallothionein
1606:Thioacetic acid
1596:
1592:
1582:
1578:
1568:
1564:
1551:
1547:
1537:
1533:
1528:Allyl mercaptan
1524:
1520:
1510:
1506:
1496:
1492:
1482:
1472:
1460:
1428:
1416:D-penicillamine
1335:can generate a
1318:
1301:
1227:
1221:
1211:
1208:
1207:
1206:
1204:
1193:
1162:
1143:
1139:
1132:
1128:
1127:
1117:
1113:
1109:
1105:
1102:R−SH + 3 H
1097:
1090:can also yield
1077:
1052:
1037:
1030:
1026:
1013:
1003:
989:
979:
972:
933:
926:
923:+ SH → ArSH + N
919:
916:
915:
914:
912:
872:
868:
864:
860:
851:
847:
843:
839:
835:
810:
806:
802:
798:
791:
787:
783:
779:
764:-alkylation of
750:
732:(X = Cl, Br, I)
729:
704:
700:
696:
692:
671:
648:
626:-exchangeable S
623:
612:
597:
595:
589:
587:
585:
580:
552:
462:found in human
460:allyl mercaptan
422:
389:
384:
361:
357:
336:
315:
293:
289:
245:
232:
177:
173:
146:
115:
103:
58:
54:
36:
35:
28:
23:
22:
15:
12:
11:
5:
4237:
4235:
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4216:
4206:
4205:
4199:
4198:
4196:
4195:
4194:
4193:
4188:
4176:
4169:
4163:
4160:
4159:
4157:
4156:
4154:Sulfinylamines
4151:
4146:
4141:
4136:
4134:Phosphoramides
4131:
4129:Isothiocyanate
4125:
4123:
4119:
4118:
4115:
4114:
4112:
4111:
4106:
4105:
4104:
4094:
4093:
4092:
4082:
4081:
4080:
4075:
4070:
4065:
4060:
4049:
4047:
4039:
4038:
4036:
4035:
4030:
4024:
4022:
4016:
4015:
4013:
4012:
4007:
4005:Selenenic acid
4002:
4000:Seleninic acid
3997:
3995:Selenonic acid
3992:
3986:
3984:
3978:
3977:
3975:
3974:
3969:
3963:
3961:
3955:
3954:
3952:
3951:
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3941:
3936:
3931:
3926:
3921:
3916:
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3906:
3901:
3896:
3891:
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3876:
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3874:
3864:
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3856:
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3849:
3847:
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3841:
3836:
3831:
3830:
3829:
3819:
3814:
3809:
3804:
3803:
3802:
3792:
3791:
3790:
3788:Phosphodiester
3779:
3777:
3771:
3770:
3768:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3717:
3712:
3707:
3702:
3697:
3692:
3687:
3682:
3677:
3672:
3667:
3666:
3665:
3660:
3649:
3647:
3638:
3634:(one element,
3618:
3617:
3614:
3613:
3611:
3610:
3609:
3608:
3598:
3597:
3596:
3591:
3580:
3578:
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3558:
3548:
3547:
3546:
3541:
3536:
3525:
3523:
3517:
3516:
3514:
3513:
3511:Methylenedioxy
3508:
3503:
3502:
3501:
3496:
3486:
3485:
3484:
3479:
3469:
3468:
3467:
3457:
3452:
3446:
3444:
3437:
3415:
3414:
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3411:
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3345:
3340:
3330:
3329:
3328:
3323:
3318:
3313:
3308:
3303:
3292:
3290:
3288:(only C and H)
3280:
3279:
3274:
3272:
3271:
3264:
3257:
3249:
3243:
3242:
3229:
3223:
3212:
3206:
3192:
3191:External links
3189:
3187:
3186:
3156:
3127:(6): 838–854.
3107:
3084:
3074:
3048:
2999:
2964:
2958:978-3527306732
2957:
2929:
2906:(3): 108–109.
2886:
2859:
2828:
2793:
2761:
2733:
2705:
2677:
2646:
2618:
2598:
2567:
2552:
2537:
2507:
2448:
2397:
2368:(2): 323–340.
2344:
2313:
2286:(9): 1865–70.
2266:
2235:
2216:(3): 159–160.
2200:
2181:(4): 493–499.
2161:
2154:
2130:
2114:"Alkanethiols"
2105:
2103:
2102:
2060:
2034:
2004:
1978:
1963:(24): 369–431.
1952:
1948:
1944:
1935:
1909:
1890:
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1855:
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1688:
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1672:
1667:
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1657:
1652:
1647:
1636:Dithiothreitol
1633:
1628:
1623:
1618:
1613:
1608:
1603:
1598:
1594:
1590:
1584:
1580:
1576:
1570:
1566:
1562:
1553:
1549:
1545:
1539:
1535:
1531:
1525:
1522:
1518:
1515:2-Propanethiol
1512:
1508:
1504:
1501:1-Propanethiol
1498:
1494:
1490:
1484:
1480:
1473:
1471:
1468:
1459:
1456:
1427:
1424:
1359:technologies.
1341:disulfide bond
1317:
1314:
1300:
1297:
1272:atom exchange
1234:thiyl radicals
1223:Main article:
1220:
1219:Thiyl radicals
1217:
1209:
1192:
1189:
1161:
1158:
1154:
1153:
1146:
1145:
1141:
1137:
1126:2 R–SH +
1120:
1119:
1115:
1111:
1107:
1103:
1095:
1092:sulfonic acids
1080:
1079:
1075:
1051:
1048:
1035:
1028:
1024:
1011:
1001:
988:
985:
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983:
971:
965:
932:
929:
928:
927:
924:
917:
892:
891:
888:
887:RLi + S → RSLi
874:
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862:
858:
854:
853:
849:
845:
841:
837:
833:
813:
812:
808:
804:
800:
796:
795:Br + NaOH → CH
793:
789:
785:
781:
777:
749:
746:
734:
733:
707:
706:
702:
698:
694:
690:
670:
667:
646:
632:H NMR spectrum
630:signal in the
621:
611:
608:
594:for X = S and
583:
579:
576:
568:polar solvents
560:boiling points
551:
548:
420:
388:
385:
383:
380:
379:
378:
375:mercaptopurine
363:
359:
355:
344:
334:
314:
311:
291:
287:
244:
241:
131:sulfanyl group
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4236:
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4095:
4091:
4088:
4087:
4086:
4083:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4055:
4054:
4051:
4050:
4048:
4046:
4045:
4040:
4034:
4033:Telluroketone
4031:
4029:
4026:
4025:
4023:
4021:
4017:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3987:
3985:
3983:
3979:
3973:
3970:
3968:
3965:
3964:
3962:
3960:
3956:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3919:Sulfonic acid
3917:
3915:
3912:
3910:
3909:Sulfinic acid
3907:
3905:
3904:Thiosulfonate
3902:
3900:
3897:
3895:
3894:Thiosulfinate
3892:
3890:
3889:Sulfenic acid
3887:
3885:
3882:
3880:
3877:
3873:
3870:
3869:
3868:
3865:
3863:
3860:
3859:
3857:
3855:
3851:
3845:
3844:Phosphaallene
3842:
3840:
3839:Phosphaalkyne
3837:
3835:
3834:Phosphaalkene
3832:
3828:
3825:
3824:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3801:
3798:
3797:
3796:
3793:
3789:
3786:
3785:
3784:
3781:
3780:
3778:
3776:
3772:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3696:
3693:
3691:
3688:
3686:
3683:
3681:
3678:
3676:
3673:
3671:
3668:
3664:
3661:
3659:
3656:
3655:
3654:
3651:
3650:
3648:
3646:
3642:
3639:
3619:
3607:
3604:
3603:
3602:
3599:
3595:
3592:
3590:
3587:
3586:
3585:
3582:
3581:
3579:
3575:
3569:
3566:
3564:
3561:
3557:
3554:
3553:
3552:
3549:
3545:
3542:
3540:
3537:
3535:
3532:
3531:
3530:
3527:
3526:
3524:
3522:
3518:
3512:
3509:
3507:
3506:Ethylenedioxy
3504:
3500:
3497:
3495:
3492:
3491:
3490:
3487:
3483:
3480:
3478:
3475:
3474:
3473:
3470:
3466:
3463:
3462:
3461:
3458:
3456:
3453:
3451:
3448:
3447:
3445:
3441:
3438:
3432:
3426:
3421:
3416:
3410:
3407:
3405:
3402:
3398:
3395:
3393:
3390:
3389:
3388:
3385:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3352:
3351:
3348:
3344:
3341:
3339:
3336:
3335:
3334:
3331:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3307:
3304:
3302:
3299:
3298:
3297:
3294:
3293:
3291:
3285:
3281:
3277:
3270:
3265:
3263:
3258:
3256:
3251:
3250:
3247:
3240:
3236:
3233:
3230:
3227:
3224:
3222:
3221:
3216:
3213:
3210:
3207:
3204:
3203:
3198:
3195:
3194:
3190:
3174:
3170:
3166:
3160:
3157:
3152:
3148:
3143:
3138:
3134:
3130:
3126:
3122:
3118:
3111:
3108:
3103:
3098:
3097:
3088:
3085:
3081:
3077:
3071:
3067:
3063:
3059:
3052:
3049:
3044:
3040:
3035:
3030:
3026:
3022:
3018:
3014:
3010:
3003:
3000:
2995:
2991:
2987:
2983:
2979:
2975:
2968:
2965:
2960:
2954:
2950:
2946:
2942:
2941:
2933:
2930:
2925:
2921:
2917:
2913:
2909:
2905:
2901:
2897:
2890:
2887:
2882:
2878:
2874:
2870:
2863:
2860:
2855:
2851:
2847:
2843:
2839:
2832:
2829:
2824:
2820:
2816:
2812:
2808:
2804:
2797:
2794:
2788:
2782:
2781:
2776:
2774:
2765:
2762:
2756:
2750:
2749:
2744:
2737:
2734:
2728:
2722:
2721:
2716:
2709:
2706:
2700:
2694:
2693:
2688:
2681:
2678:
2673:
2669:
2665:
2661:
2657:
2650:
2647:
2641:
2635:
2634:
2629:
2622:
2619:
2616:
2612:
2608:
2602:
2599:
2586:
2582:
2578:
2571:
2568:
2563:
2556:
2553:
2548:
2541:
2538:
2525:
2521:
2517:
2511:
2508:
2503:
2499:
2494:
2489:
2484:
2479:
2475:
2471:
2467:
2463:
2459:
2452:
2449:
2444:
2440:
2436:
2432:
2428:
2424:
2420:
2416:
2412:
2408:
2401:
2398:
2393:
2389:
2384:
2379:
2375:
2371:
2367:
2363:
2359:
2357:
2348:
2345:
2332:
2328:
2324:
2317:
2314:
2309:
2305:
2301:
2297:
2293:
2289:
2285:
2281:
2277:
2270:
2267:
2262:
2258:
2254:
2250:
2246:
2239:
2236:
2231:
2227:
2223:
2219:
2215:
2211:
2204:
2201:
2196:
2192:
2188:
2184:
2180:
2176:
2172:
2165:
2162:
2157:
2155:0-8493-0487-3
2151:
2147:
2143:
2142:
2134:
2131:
2119:
2115:
2109:
2106:
2099:
2095:
2091:
2087:
2083:
2079:
2075:
2071:
2065:
2061:
2058:
2052:
2048:
2044:
2040:
2035:
2031:
2027:
2023:
2019:
2015:
2011:
2005:
2001:
1997:
1993:
1989:
1985:
1979:
1976:
1972:
1968:
1965:From p. 378:
1962:
1958:
1942:
1936:
1931:
1927:
1923:
1918:
1917:
1913:
1910:
1906:
1902:
1897:
1895:
1891:
1886:
1880:
1876:
1869:
1867:
1863:
1858:
1856:9780470771327
1852:
1848:
1844:
1840:
1833:
1830:
1825:
1823:9780470771310
1819:
1815:
1811:
1807:
1800:
1798:
1794:
1791:
1787:
1784:
1780:
1779:
1773:
1770:
1767:
1763:
1759:
1756:
1751:
1748:
1745:
1741:
1738:
1734:
1733:
1727:
1724:
1718:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1690:
1686:
1681:
1678:
1676:
1673:
1671:
1668:
1666:
1663:
1661:
1658:
1656:
1653:
1651:
1648:
1645:
1641:
1637:
1634:
1632:
1629:
1627:
1624:
1622:
1619:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1588:
1585:
1574:
1573:Pentanethiols
1571:
1560:
1558:
1554:
1543:
1540:
1529:
1526:
1516:
1513:
1502:
1499:
1488:
1485:
1478:
1475:
1474:
1469:
1467:
1465:
1457:
1455:
1453:
1449:
1445:
1441:
1437:
1433:
1425:
1423:
1421:
1417:
1413:
1410:(anticancer)
1409:
1406:
1402:
1400:
1396:
1392:
1389:
1385:
1381:
1377:
1373:
1369:
1365:
1360:
1358:
1354:
1350:
1346:
1342:
1338:
1334:
1330:
1326:
1323:
1315:
1310:
1305:
1298:
1296:
1294:
1293:free radicals
1290:
1285:
1283:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1251:
1247:
1243:
1239:
1235:
1231:
1230:Free radicals
1226:
1225:Thiyl radical
1218:
1216:
1202:
1198:
1191:Thioxanthates
1190:
1188:
1186:
1182:
1178:
1175:
1171:
1167:
1159:
1157:
1151:
1150:
1149:
1125:
1124:
1123:
1101:
1100:
1099:
1093:
1089:
1085:
1073:
1072:
1071:
1069:
1065:
1061:
1057:
1049:
1043:
1039:
1034:
1022:
1018:
1014:
1010:
1004:
1000:
994:
986:
977:
976:
975:
969:
966:
964:
962:
958:
954:
950:
946:
942:
938:
930:
911:
910:
909:
907:
902:
899:
897:
889:
886:
885:
884:
882:
878:
856:
855:
831:
830:
829:
827:
823:
819:
794:
775:
774:
773:
771:
767:
763:
759:
755:
747:
745:
743:
739:
727:
726:
725:
723:
718:
716:
712:
688:
687:
686:
684:
680:
676:
668:
666:
664:
660:
656:
652:
645:
641:
637:
633:
629:
625:
617:
609:
607:
605:
604:thiyl radical
577:
575:
573:
569:
565:
562:and are less
561:
557:
549:
547:
545:
541:
537:
533:
531:
526:
522:
518:
514:
510:
505:
503:
499:
498:monoterpenoid
495:
491:
487:
482:
480:
476:
471:
469:
465:
461:
457:
455:
450:
446:
442:
438:
434:
433:semiochemical
430:
426:
418:
414:
410:
406:
402:
398:
394:
386:
381:
376:
372:
368:
364:
353:
349:
345:
342:
341:
332:
328:
324:
320:
319:
318:
312:
310:
308:
307:dipole moment
304:
300:
295:
286:(BDE). For CH
285:
280:
278:
274:
270:
266:
262:
258:
254:
250:
242:
240:
238:
230:
225:
221:
217:
213:
207:
171:
167:
163:
159:
154:
152:
144:
140:
136:
132:
128:
124:
120:
113:
109:
101:
97:
93:
89:
85:
82:
81:Ancient Greek
76:
52:
48:
34:Thiol with a
32:
19:
4178:
4171:
4085:Vinyl halide
4042:
3972:Borinic acid
3967:Boronic acid
3944:Thioxanthate
3861:
3284:Hydrocarbons
3218:
3200:
3177:. Retrieved
3168:
3159:
3124:
3120:
3110:
3095:
3087:
3079:
3057:
3051:
3016:
3012:
3002:
2977:
2973:
2967:
2938:
2932:
2903:
2899:
2889:
2872:
2868:
2862:
2845:
2841:
2831:
2806:
2802:
2796:
2786:
2778:
2772:
2764:
2754:
2746:
2736:
2726:
2718:
2708:
2698:
2690:
2680:
2663:
2659:
2655:
2649:
2639:
2631:
2621:
2606:
2601:
2589:. Retrieved
2580:
2570:
2564:. CRC Press.
2561:
2555:
2546:
2540:
2528:. Retrieved
2519:
2510:
2465:
2461:
2451:
2410:
2406:
2400:
2365:
2361:
2355:
2347:
2335:. Retrieved
2316:
2283:
2279:
2275:
2269:
2252:
2248:
2244:
2238:
2213:
2209:
2203:
2178:
2174:
2170:
2164:
2139:
2133:
2121:. Retrieved
2108:
2077:
2073:
2063:
2046:
2042:
2017:
2013:
1991:
1987:
1974:
1970:
1966:
1960:
1956:
1929:
1925:
1912:
1900:
1874:
1838:
1832:
1805:
1776:
1772:
1765:
1750:
1730:
1726:
1556:
1477:Methanethiol
1461:
1440:biosynthesis
1429:
1404:
1403:
1361:
1339:unit with a
1331:folding, an
1319:
1286:
1242:biochemistry
1228:
1201:thioxanthate
1194:
1176:
1169:
1163:
1155:
1147:
1121:
1114:H + 3 H
1081:
1053:
1032:
1031:SH) with a p
1008:
998:
992:
990:
973:
967:
934:
905:
903:
900:
895:
893:
875:
818:dithioketals
814:
761:
757:
751:
735:
719:
708:
683:methanethiol
672:
643:
627:
613:
581:
553:
529:
506:
483:
472:
453:
412:
408:
390:
370:
366:
351:
347:
340:methanethiol
338:
337:SH would be
322:
316:
313:Nomenclature
296:
281:
265:bond lengths
261:alkyl thiols
260:
257:alkanethiols
256:
246:
228:
211:
169:
155:
150:
130:
126:
122:
102:of the form
95:
87:
84:
50:
44:
4149:Thiocyanate
4144:Sulfonamide
4109:Perchlorate
4097:Acyl halide
4058:Fluoroethyl
3939:Thionoester
3827:Phosphonium
3812:Phosphinate
3807:Phosphonous
3795:Phosphonate
3494:Hydroperoxy
3316:Cyclopropyl
2848:: 179–224.
2362:J. Exp. Med
2249:Tetrahedron
2123:4 September
2020:(1): 1–10.
1616:Glutathione
1542:Butanethiol
1487:Ethanethiol
1448:hydrocarbon
1364:active site
1266:glutathione
1168:. The term
1140:→ RS−SR + H
1070:(R−S−S−R).
970:-Alkylation
941:thioacetals
852:→ Na + NaCl
669:Preparation
651:IR spectrum
536:ethanethiol
517:natural gas
513:ethanethiol
509:natural gas
475:wine faults
449:ethanethiol
367:sulfhydryl-
321:The suffix
239:compounds.
166:natural gas
123:thiol group
112:substituent
79:; from
4208:Categories
4053:Haloalkane
3924:Thioketone
3879:Persulfide
3775:Phosphorus
3740:Isocyanate
3730:Isonitrile
3631:or oxygen
3629:hydrogen,
3625:not being
3606:Orthoester
3499:Dioxiranes
3477:Enol ether
3365:1-Propenyl
2869:Org. Synth
2660:Org. Synth
2337:January 2,
1719:References
1703:Persulfide
1611:Coenzyme A
1587:Thiophenol
1452:coenzyme M
1436:Coenzyme A
1322:amino acid
1289:scavengers
1274:equilibria
982:(B = base)
945:thioesters
822:Bunte salt
803:SH + OC(NH
784:Br + SC(NH
754:haloalkane
502:grapefruit
492:, whereas
407:contains (
269:picometres
253:sulfhydryl
170:mercaptans
4186:inorganic
4020:Tellurium
3934:Thioester
3899:Sulfoxide
3884:Disulfide
3872:Sulfonium
3822:Phosphine
3800:Phosphite
3783:Phosphate
3715:Carbamate
3690:Hydrazone
3623:element,
3621:Only one
3594:Anhydride
3333:Methylene
3215:Mercaptan
2974:Chem. Rev
2823:196805424
2146:CRC Press
2049:: 87–97.
1969:Mercaptum
1783:mercaptan
1458:In skunks
1432:cofactors
1426:Cofactors
1412:Captopril
1376:substrate
1370:can form
1254:homolysis
1170:mercaptan
1068:disulfide
961:alkoxides
931:Reactions
869:H + NaHSO
653:. In the
371:mercapto-
365:The term
350:replaces
348:mercaptan
346:The word
333:, e.g. CH
98:, is any
18:Mercaptan
4167:See also
4102:Chloride
4028:Tellurol
3982:Selenium
3949:Xanthate
3663:Ammonium
3645:Nitrogen
3627:carbon,
3584:Carboxyl
3551:Aldehyde
3539:Acryloyl
3521:carbonyl
3425:hydrogen
3380:Cumulene
3235:Archived
3173:Archived
3151:17592500
3043:20882988
2994:12797828
2924:Archived
2920:97292021
2585:Archived
2524:Archived
2502:22328155
2435:15724148
2392:19866801
2331:Archived
2308:19217201
2300:12449512
2098:Archived
2051:Archived
2030:Archived
1786:Archived
1758:Archived
1740:Archived
1698:Odorizer
1687:See also
1644:epimeric
1626:Cysteine
1521:CH(SH)CH
1325:cysteine
1270:hydrogen
1199:to give
1056:oxidized
993:thiolate
937:sulfides
861:O → HSCH
766:thiourea
679:methanol
544:catalyst
468:thietane
229:thiolate
162:odorants
143:hydroxyl
135:alcohols
88:(theion)
4191:organic
3990:Selenol
3914:Sulfone
3867:Sulfide
3765:NONOate
3760:Nitroso
3750:Nitrite
3745:Nitrate
3735:Cyanate
3725:Nitrile
3710:Amidine
3705:Imidate
3675:Nitrene
3670:Hydrazo
3658:Enamine
3589:Acetoxy
3577:carboxy
3544:Benzoyl
3482:Epoxide
3465:Methoxy
3455:Alcohol
3409:Carbene
3343:Methine
3142:2078229
3034:2956374
2875:: 147.
2803:Synlett
2493:3295281
2470:Bibcode
2415:Bibcode
2383:2117909
2218:Bibcode
2195:9451251
2082:Bibcode
1971:(von:
1932:: 1–70.
1444:methane
1349:peptide
1337:cystine
1329:protein
1181:mercury
1136: O
1131:⁄
1060:bromine
987:Acidity
953:acetals
711:alkenes
578:Bonding
572:isomers
564:soluble
427:urine.
352:alcohol
237:mercury
231:group (
141:in the
129:, or a
94:'), or
90: '
4214:Thiols
4090:Iodide
4010:Selone
3854:Sulfur
3563:Ketone
3556:Ketene
3534:Acetyl
3489:Peroxy
3460:Alkoxy
3450:Acetal
3431:oxygen
3420:carbon
3404:Alkyne
3397:Benzyl
3392:Phenyl
3375:Allene
3370:Crotyl
3350:Alkene
3338:Bridge
3326:Pentyl
3311:Propyl
3301:Methyl
3149:
3139:
3072:
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2992:
2955:
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2500:
2490:
2443:162036
2441:
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2407:Nature
2390:
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1464:skunks
1438:. The
1368:enzyme
1366:of an
1278:carbon
1064:iodine
1017:phenol
980:
957:esters
955:, and
949:ethers
943:, and
857:Na + H
840:H + Na
811:+ NaBr
730:
715:Halide
701:SH + H
697:S → CH
693:OH + H
588:365.07
490:coffee
464:garlic
445:OR2T11
441:Copper
401:skunks
397:garlic
323:-thiol
158:garlic
139:oxygen
114:. The
92:sulfur
37:
4122:Other
3959:Boron
3929:Thial
3862:Thiol
3755:Nitro
3720:Imide
3700:Amide
3685:Oxime
3680:Imine
3653:Amine
3601:Ester
3568:Ynone
3472:Ether
3443:R-O-R
3418:Only
3360:Allyl
3355:Vinyl
3321:Butyl
3306:Ethyl
3296:Alkyl
3217:, by
3179:3 May
3104:, 83.
2916:S2CID
2819:S2CID
2591:3 May
2530:3 May
2439:S2CID
2304:S2CID
2191:S2CID
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1916:See:
1755:θεῖον
1737:thiol
1646:pair)
1561:– (CH
1534:=CHCH
1430:Many
1246:alkyl
1174:Latin
1110:→ RSO
1050:Redox
740:from
677:with
596:440.2
515:, to
479:yeast
425:mouse
417:onion
405:sweat
393:odors
331:IUPAC
299:polar
249:alkyl
220:Latin
210:) or
151:thio-
125:or a
108:alkyl
86:θεῖον
83:
51:thiol
4044:Halo
3529:Acyl
3429:and
3387:Aryl
3181:2018
3147:PMID
3070:ISBN
3039:PMID
2990:PMID
2953:ISBN
2593:2018
2532:2018
2498:PMID
2431:PMID
2388:PMID
2339:2008
2296:PMID
2247:)".
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2150:ISBN
2125:2019
1951:)HSO
1879:ISBN
1851:ISBN
1818:ISBN
1642:(an
1569:CSH
1557:tert
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1479:– CH
1250:aryl
1240:and
1205:RSCS
1098:H).
1094:(RSO
1062:and
879:and
832:ClCH
792:→ Br
661:and
496:, a
451:and
437:mice
387:Odor
104:R−SH
49:, a
3695:Azo
3199:at
3137:PMC
3129:doi
3125:152
3062:doi
3029:PMC
3021:doi
2982:doi
2978:103
2945:doi
2908:doi
2877:doi
2850:doi
2811:doi
2668:doi
2611:doi
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2478:doi
2466:109
2423:doi
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2378:PMC
2370:doi
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2278:".
2257:doi
2226:doi
2183:doi
2090:doi
2078:107
2022:doi
1996:doi
1843:doi
1810:doi
1589:– C
1583:SH
1575:– C
1552:SH
1544:– C
1538:SH
1511:SH
1503:– C
1497:SH
1489:– C
1483:SH
1442:of
1382:in
1291:of
1258:DNA
1248:or
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1086:or
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640:NMR
638:is
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