927:
875:
950:
20:
131:
852:
1111:
890:
1165:
908:
1132:
1282:
Whereas benzenesulfonic acid hydrolyzes above 200 °C, many derivatives are easier to hydrolyze. Thus, heating aryl sulfonic acids in aqueous acid produces the parent arene. This reaction is employed in several scenarios. In some cases the sulfonic acid serves as a water-solubilizing protecting
826:
Because of their polarity, sulfonic acids tend to be crystalline solids or viscous, high-boiling liquids. They are also usually colourless and nonoxidizing, which makes them suitable for use as acid catalysts in organic reactions. Their polarity, in conjunction with their high acidity, renders
1152:
for paper-making, lignin is removed from the lignocellulose by treating wood chips with solutions of sulfite and bisulfite ions. These reagents cleave the bonds between the cellulose and lignin components and especially within the lignin itself. The lignin is converted to
1435:
The conditions for this reaction are harsh, however, requiring 'fused alkali' or molten sodium hydroxide at 350 °C for benzenesulfonic acid itself. Unlike the mechanism for the fused alkali hydrolysis of chlorobenzene, which proceeds through elimination-addition
1391:
bond can be broken by nucleophilic reagents. Of historic and continuing significance is the α-sulfonation of anthroquinone followed by displacement of the sulfonate group by other nucleophiles, which cannot be installed directly. An early method for producing
704:
of octanesulfonic acid. Similarly the sulfonyl chloride derived from polyethylene is hydrolyzed to the sulfonic acid. These sulfonyl chlorides are produced by free-radical reactions of chlorine, sulfur dioxide, and the hydrocarbons using the
1476:
Neither the parent sulfonic acid nor the parent sulfurous acid have been isolated or even observed, although the monoanion of these hypothetical species exists in solution as an equilibrium mixture of tautomers:
525:
838:
OH features a tetrahedral sulfur centre, meaning that sulfur is at the center of four atoms: three oxygens and one carbon. The overall geometry of the sulfur centre is reminiscent of the shape of
598:
380:
926:
260:
675:
790:
values cannot be measured directly, and values commonly quoted should be regarded as indirect estimates with significant uncertainties. For instance, various sources have reported the p
1287:, phenol is converted to its 4-sulfonic acid derivative, which then selectively chlorinates at the positions flanking the phenol. Hydrolysis releases the sulfonic acid group.
851:
949:
1444:
Ar mechanism, as revealed by a C labeling, despite the lack of stabilizing substituents. Sulfonic acids with electron-withdrawing groups (e.g., with NO
1869:
1732:
1541:
999:. Since the mid-20th century, the usage of sulfonic acids has surpassed soap in advanced societies. For example, an estimated 2 billion kilograms of
874:
2997:
2038:
889:
2957:
414:
2962:
1934:
Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in
Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH.
797:
of methanesulfonic acid to be as high as −0.6 or as low as −6.5. Sulfonic acids are known to react with solid sodium chloride (
1919:
1820:
1651:
1618:
976:
Both alkyl and aryl sulfonic acids are known, most large-scale applications are associated with the aromatic derivatives.
907:
750:
Sulfonic acids are strong acids. They are commonly cited as being around a million times stronger than the corresponding
531:
302:
274:
159:
1886:
1749:
1675:
Gernon, Michael D.; Wu, Min; Buszta, Thomas; Janney, Patrick (1999). "Environmental benefits of methanesulfonic acid".
1558:
1521:
613:
2990:
2031:
1283:
group, as illustrated by the purification of para-xylene via its sulfonic acid derivative. In the synthesis of
932:
805:
and hydrogen chloride. This property implies an acidity within two or three orders of magnitude of that of HCl
1902:
Boswell, G. A.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. (2011). "Fluorination by Sulfur
Tetrafluoride".
2861:
3867:
697:
2983:
1803:
Tanaka, Kazuhiko (1991). "Sulfonic Acids, Esters, Amides and
Halides as Synthons". In Saul Patai (ed.).
3899:
2434:
2024:
1709:
Kosswig, K. "Surfactants" in
Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.
766:
1082:
as acids that are lipophilic (soluble in organic solvents). Polymeric sulfonic acids are also useful.
1730:
Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2002). "Anthraquinone Dyes and
Intermediates".
827:
short-chain sulfonic acids water-soluble, while longer-chain ones exhibit detergent-like properties.
150:
1952:
Bunnett, Joseph F.; Zahler, Roland E. (1951-10-01). "Aromatic
Nucleophilic Substitution Reactions".
1456:
Arylsulfonic acids react with two equiv of butyl lithium to give the ortho-lithio derivatives, i.e.
2471:
385:
Direct reaction of alkanes with sulfur trioxide is not generally useful, except for the conversion
3894:
3691:
2944:
3638:
2844:
1236:
1125:
1072:
1044:
895:
755:
390:
40:
3770:
3375:
2951:
2839:
1177:
The reactivity of the sulfonic acid group is so extensive that it is difficult to summarize.
1000:
292:. This reaction is employed industrially to produce alkyl sulfonic acids, which are used as
783:
are 4.20 and 4.76, respectively. However, as a consequence of their strong acidity, their p
3467:
2920:
2365:
1353:
1241:
Arylsulfonic acids are susceptible to hydrolysis, the reverse of the sulfonation reaction:
1118:
1060:
831:
762:
386:
134:
1003:
are produced annually for diverse purposes. Lignin sulfonates, produced by sulfonation of
8:
3545:
3509:
3400:
3312:
3055:
3045:
2226:
1136:
701:
3803:
3658:
3571:
3527:
3317:
3006:
1574:
Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution".
1284:
1098:, a fluorinated polymeric sulfonic acid is a component of proton exchange membranes in
1027:
dyes are produced or processed via sulfonation. Sulfonic acids tend to bind tightly to
712:
19:
700:
is prepared by hydrolysis of the sulfonyl fluoride, which in turn is generated by the
3723:
3705:
3585:
3411:
3229:
3224:
3210:
3122:
3117:
3050:
2910:
2880:
2638:
2260:
1969:
1915:
1882:
1816:
1782:
1745:
1692:
1657:
1647:
1624:
1614:
1591:
1554:
1517:
1316:
1079:
940:
28:
1185:
When treated with strong base, benzenesulfonic acid derivatives convert to phenols.
3856:
3560:
3481:
3357:
3274:
3157:
3082:
3077:
3066:
2615:
2109:
2047:
2000:
1961:
1935:
1907:
1874:
1867:
Otto
Lindner; Lars Rodefeld (2005). "Benzenesulfonic Acids and Their Derivatives".
1849:
1808:
1774:
1737:
1710:
1684:
1583:
1546:
1457:
1397:
1349:
1312:
1300:
991:
are molecules that combine highly nonpolar and highly polar groups. Traditionally,
111:
1939:
3752:
3653:
3495:
3239:
3234:
3147:
2834:
2593:
2588:
2571:
2554:
2355:
2104:
1308:
1149:
1091:
798:
693:
146:
87:(with the organic substituent replaced by hydrogen) is the parent sulfonic acid,
84:
1987:
Oae, Shigeru; Furukawa, Naomichi; Kise, Masahiro; Kawanishi, Mitsuyoshi (1966).
1911:
130:
23:
General structure of a sulfonic acid with the functional group indicated in blue
3814:
3734:
3663:
3327:
3107:
2905:
2900:
2776:
2771:
2766:
2559:
2526:
2310:
2292:
2282:
1154:
1008:
716:
285:
100:
1460:. These dilithio compounds are poised for reactions with many electrophiles.
3888:
3828:
3677:
3596:
3386:
3298:
3284:
3264:
3196:
3162:
3127:
3017:
2925:
2873:
2804:
2680:
2675:
2665:
2660:
2610:
2605:
2521:
2516:
2506:
2360:
2315:
2277:
2265:
2236:
2114:
1973:
1878:
1853:
1741:
1714:
1696:
1661:
1628:
1595:
1550:
1024:
839:
706:
281:
76:
1812:
3842:
3788:
3624:
3610:
3453:
3439:
3337:
3167:
3137:
3087:
3031:
2856:
2743:
2738:
2715:
2466:
2305:
2231:
2168:
2163:
2141:
2097:
2082:
2072:
1786:
1765:
Busca, Guido (2007). "Acid
Catalysts in Industrial Hydrocarbon Chemistry".
1440:
mechanism), benzenesulfonic acid undergoes the analogous conversion by an S
1032:
864:, and one of the few naturally occurring sulfonic acids (shown in uncommon
776:
405:
266:
3347:
3244:
3097:
2915:
2868:
2829:
2710:
2598:
2583:
2578:
2566:
2131:
2126:
2092:
2087:
2077:
2055:
2005:
1988:
1509:
1320:
1114:
1087:
963:
780:
142:
80:
1965:
1611:
March's advanced organic chemistry: reactions, mechanisms, and structure
1587:
1110:
3425:
3254:
2824:
2815:
2695:
2650:
2546:
2511:
2501:
2441:
2377:
2300:
2248:
1164:
996:
988:
955:
936:
401:
293:
1778:
1161:, which are soluble and can be separated from the cellulose fibers.
2975:
2791:
2705:
2670:
2655:
2643:
2486:
2461:
2270:
1688:
1352:. Sulfonyl fluorides can be produced by treating sulfonic acids with
1099:
984:
917:
861:
802:
397:
119:
2016:
1642:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart G. (January 2012).
1227:
In this case the sulfonate behaves as a pseudohalide leaving group.
1168:
idealized scheme for lignin depolymerization by the
Sulfite process.
1131:
3332:
2799:
2753:
2720:
2416:
2322:
2196:
2151:
2136:
1448:
or CN substituents) undergo this transformation much more readily.
1056:
1040:
1012:
865:
751:
739:
738:), which in turn is obtained by the addition of sulfur trioxide to
96:
68:
2761:
2685:
2536:
2531:
2496:
2481:
2476:
2446:
2429:
2253:
2180:
2146:
1437:
1158:
1028:
959:
857:
830:
The structure of sulfonic acids is illustrated by the prototype,
681:
1514:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
149:. A large scale application of this method is the production of
2849:
2781:
2625:
2334:
2327:
2221:
2202:
2191:
2175:
2121:
1393:
1128:, a class of antibacterials, are produced from sulfonic acids.
1095:
1004:
913:
289:
1989:"The Mechanism of the Alkaline Fusion of Benzenesulfonic Acid"
520:{\displaystyle {\ce {HSO3- + RCH=CH2 + H+ -> RCH2CH2SO3H}}}
396:
Many alkane sulfonic acids can be obtained by the addition of
2730:
2700:
2633:
2491:
2456:
2451:
2424:
2372:
2339:
2243:
2067:
1296:
1083:
604:
270:
115:
52:
1807:. PATAI'S Chemistry of Functional Groups. pp. 401–452.
2158:
1901:
992:
880:
56:
1866:
1348:−X) are produced by chlorination of sulfonic acids using
1036:
660:
644:
570:
510:
497:
484:
455:
365:
349:
323:
245:
232:
219:
203:
187:
174:
1986:
280:
Alkylsulfonic acids can be prepared by many methods. In
775:
values of −2.8 and −1.9, respectively, while those of
624:
329:
1729:
616:
593:{\displaystyle {\ce {HSO3- + RBr -> RSO3H + Br-}}}
534:
417:
375:{\displaystyle {\ce {RH + SO2 + 1/2 O2 -> RSO3H}}}
305:
162:
1805:
Sulphonic Acids, Esters and their Derivatives (1991)
1674:
1641:
1055:
Being strong acids, sulfonic acids are also used as
1613:(6th ed.). Hoboken, N.J.: Wiley-Interscience.
1539:Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic".
273:is the nucleophile. The reaction is an example of
255:{\displaystyle {\ce {RC6H5 + SO3 -> RC6H4SO3H}}}
141:Aryl sulfonic acids are produced by the process of
692:Many sulfonic acids are prepared by hydrolysis of
669:
592:
519:
374:
254:
1646:(2nd ed.). Oxford: Oxford University Press.
958:, is a cofactor required for the biosynthesis of
680:This pathway is the basis of the biosynthesis of
3886:
1117:is a sulfonic acid-containing drug use to treat
995:are the popular surfactants, being derived from
670:{\displaystyle {\ce {RSH + 3/2 O2 -> RSO3H}}}
16:Organic compounds with the structure R−S(=O)2−OH
1400:, which can be generated readily from benzene.
1090:and is used as catalysts and for ion exchange (
603:Sulfonic acids can be prepared by oxidation of
79:with one hydroxyl group replaced by an organic
1870:Ullmann's Encyclopedia of Industrial Chemistry
1733:Ullmann's Encyclopedia of Industrial Chemistry
1542:Ullmann's Encyclopedia of Industrial Chemistry
1319:. Such sulfonate esters are often prepared by
71:hydroxide. As a substituent, it is known as a
2991:
2032:
1951:
1835:
979:
901:, a widely used reagent in organic synthesis.
883:, a surfactant and a controversial pollutant.
1725:
1723:
1508:
1382:
846:Representative sulfonic acids and sulfonates
400:to terminal alkenes. Bisulfite can also be
1230:
1039:are sulfonic acids (or have the functional
284:, alkanes are irradiated with a mixture of
2998:
2984:
2039:
2025:
1608:
2004:
1993:Bulletin of the Chemical Society of Japan
1720:
1798:
1796:
1573:
1180:
1163:
1130:
1109:
265:In this reaction, sulfur trioxide is an
129:
75:. A sulfonic acid can be thought of as
18:
1928:
1895:
1538:
1504:
1502:
1396:involved the base hydrolysis of sodium
1086:resin are sulfonic acid derivatives of
3887:
3005:
1802:
1534:
1532:
916:, a polymeric sulfonic acid useful in
2979:
2046:
2020:
1793:
1764:
1609:Smith, Michael; March, Jerry (2007).
816:was recently accurately determined (p
39:) refers to a member of the class of
1499:
687:
1529:
1295:Sulfonic acids can be converted to
275:electrophilic aromatic substitution
145:. Usually the sulfonating agent is
13:
1143:
1011:and additives in certain kinds of
14:
3911:
1516:(4th ed.), New York: Wiley,
1290:
1135:Sulfonates are the basis of most
1050:
1043:group in them) for this reason.
948:
925:
906:
888:
873:
850:
1980:
1945:
1860:
1829:
1758:
1451:
1387:Although strong, the (aryl)C−SO
1339:
971:
696:and related precursors. Thus,
1703:
1668:
1635:
1602:
1567:
1470:
1078:, which are regularly used in
933:Sodium dodecylbenzenesulfonate
834:. The sulfonic acid group, RSO
647:
557:
471:
352:
206:
125:
1:
1940:10.1002/14356007.a19_299.pub2
1576:Accounts of Chemical Research
1492:
1307:−OR. Sulfonic esters such as
745:
118:of sulfonic acids are called
1344:Sulfonyl halide groups (R−SO
1303:has the general formula R−SO
1172:
1059:. The simplest examples are
715:is derived by hydrolysis of
698:perfluorooctanesulfonic acid
7:
1912:10.1002/0471264180.or021.01
1323:of the sulfonyl chlorides:
1047:is used to make food dyes.
935:, an alkylbenzenesulfonate
10:
3916:
1234:
980:Detergents and surfactants
151:alkylbenzenesulfonic acids
3013:
2934:
2893:
2813:
2790:
2752:
2729:
2624:
2545:
2415:
2392:
2348:
2291:
2214:
2189:
2054:
1383:Displacement by hydroxide
43:with the general formula
1879:10.1002/14356007.a03_507
1854:10.15227/orgsyn.003.0037
1742:10.1002/14356007.a02_355
1715:10.1002/14356007.a25_747
1551:10.1002/14356007.a25_503
1463:
1231:Hydrolytic desulfonation
1139:used in water softening.
1105:
1045:p-Cresidinesulfonic acid
1023:Many if not most of the
137:of methanesulfonic acid.
51:, where R is an organic
2945:chemical classification
1873:. Weinheim: Wiley-VCH.
1836:W. W. Hartman (1923). "
1813:10.1002/0470034394.ch11
1736:. Weinheim: Wiley-VCH.
1545:. Weinheim: Wiley-VCH.
1018:
1237:Desulfonation reaction
1169:
1140:
1122:
1001:alkylbenzenesulfonates
671:
594:
521:
391:methanedisulfonic acid
376:
256:
138:
41:organosulfur compounds
24:
2952:chemical nomenclature
1181:Hydrolysis to phenols
1167:
1134:
1113:
1076:-toluenesulfonic acid
899:-Toluenesulfonic acid
801:) to form the sodium
759:-Toluenesulfonic acid
672:
595:
522:
377:
257:
133:
22:
2006:10.1246/bcsj.39.1212
1354:sulfur tetrafluoride
1311:are considered good
1119:alcohol use disorder
1061:methanesulfonic acid
832:methanesulfonic acid
763:methanesulfonic acid
614:
532:
415:
387:methanesulfonic acid
303:
160:
135:Ball-and-stick model
2408:not C, H or O)
1966:10.1021/cr60153a002
1588:10.1021/ar00156a004
1137:ion exchange resins
754:acid. For example,
702:electrofluorination
662:
646:
572:
550:
512:
499:
486:
457:
433:
367:
351:
325:
247:
234:
221:
205:
189:
176:
3007:Hydrogen compounds
2850:Hypervalent iodine
1906:. pp. 1–124.
1483:(O) ⇌ S(=O)(OH)(O)
1285:2,6-dichlorophenol
1170:
1141:
1123:
1035:. Most "washable"
1007:are components of
941:laundry detergents
713:Vinylsulfonic acid
667:
650:
634:
633:
590:
560:
536:
517:
500:
487:
474:
445:
419:
372:
355:
339:
338:
313:
252:
235:
222:
209:
193:
177:
164:
139:
25:
3900:Functional groups
3882:
3881:
2973:
2972:
2911:Sulfenyl chloride
2889:
2888:
2388:
2387:
2207:(only C, H and O)
2048:Functional groups
1921:978-0-471-26418-7
1904:Organic Reactions
1842:Organic Syntheses
1822:978-0-470-03439-2
1779:10.1021/cr068042e
1773:(11): 5366–5410.
1653:978-0-19-166621-6
1644:Organic chemistry
1620:978-1-61583-842-4
1317:organic synthesis
1313:alkylating agents
1301:organic compounds
1080:organic chemistry
688:Hydrolysis routes
665:
653:
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29:organic chemistry
3907:
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3192:
3177:
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3143:
3133:
3113:
3103:
3093:
3073:
3062:
3041:
3027:
3000:
2993:
2986:
2977:
2976:
2940:
2845:Trifluoromethoxy
2413:
2412:
2409:
2212:
2211:
2208:
2061:
2041:
2034:
2027:
2018:
2017:
2011:
2010:
2008:
1999:(6): 1212–1216.
1984:
1978:
1977:
1954:Chemical Reviews
1949:
1943:
1932:
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1707:
1701:
1700:
1689:10.1039/A900157C
1672:
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1639:
1633:
1632:
1606:
1600:
1599:
1571:
1565:
1564:
1536:
1527:
1526:
1506:
1486:
1484:
1474:
1458:ortho-lithiation
1398:benzenesulfonate
1378:
1350:thionyl chloride
1299:. This class of
1278:
1223:
1202:H + 2 NaOH → C
952:
929:
910:
892:
877:
854:
737:
694:sulfonyl halides
676:
674:
673:
668:
666:
663:
661:
658:
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50:
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3908:
3906:
3905:
3904:
3885:
3884:
3883:
3878:
3872:
3868:
3861:
3857:
3851:
3847:
3843:
3837:
3833:
3829:
3823:
3819:
3815:
3808:
3804:
3797:
3793:
3789:
3783:
3779:
3775:
3771:
3765:
3761:
3757:
3753:
3747:
3743:
3739:
3735:
3728:
3724:
3718:
3714:
3710:
3706:
3700:
3696:
3692:
3686:
3682:
3678:
3672:
3668:
3664:
3647:
3643:
3639:
3633:
3629:
3625:
3619:
3615:
3611:
3605:
3601:
3597:
3590:
3586:
3580:
3576:
3572:
3565:
3561:
3554:
3550:
3546:
3540:
3536:
3532:
3528:
3522:
3518:
3514:
3510:
3504:
3500:
3496:
3490:
3486:
3482:
3476:
3472:
3468:
3462:
3458:
3454:
3448:
3444:
3440:
3434:
3430:
3426:
3420:
3416:
3412:
3405:
3401:
3395:
3391:
3387:
3380:
3376:
3370:
3366:
3362:
3358:
3352:
3348:
3342:
3338:
3322:
3318:
3307:
3303:
3299:
3293:
3289:
3285:
3279:
3275:
3269:
3265:
3259:
3255:
3249:
3245:
3219:
3215:
3211:
3205:
3201:
3197:
3191:
3187:
3183:
3179:
3176:
3172:
3168:
3152:
3148:
3142:
3138:
3132:
3128:
3112:
3108:
3102:
3098:
3092:
3088:
3071:
3067:
3060:
3056:
3040:
3036:
3032:
3026:
3022:
3018:
3009:
3004:
2974:
2969:
2938:
2930:
2885:
2840:Trichloromethyl
2835:Trifluoromethyl
2809:
2786:
2748:
2725:
2620:
2589:Phosphine oxide
2541:
2407:
2405:
2404:
2402:
2400:
2398:
2396:
2394:
2384:
2344:
2287:
2206:
2205:
2200:
2195:
2185:
2059:
2058:
2050:
2045:
2015:
2014:
1985:
1981:
1950:
1946:
1933:
1929:
1922:
1900:
1896:
1889:
1865:
1861:
1834:
1830:
1823:
1801:
1794:
1763:
1759:
1752:
1728:
1721:
1708:
1704:
1677:Green Chemistry
1673:
1669:
1654:
1640:
1636:
1621:
1607:
1603:
1582:(12): 456–463.
1572:
1568:
1561:
1537:
1530:
1524:
1507:
1500:
1495:
1490:
1489:
1482:
1478:
1475:
1471:
1466:
1454:
1447:
1443:
1431:
1427:
1423:
1419:
1415:
1411:
1407:
1390:
1385:
1376:
1372:
1368:
1364:
1360:
1347:
1342:
1334:
1331:Cl + R′OH → RSO
1330:
1309:methyl triflate
1306:
1293:
1277:
1273:
1269:
1265:
1261:
1257:
1253:
1249:
1245:
1239:
1233:
1221:
1217:
1213:
1209:
1205:
1201:
1197:
1193:
1189:
1183:
1175:
1155:lignosulfonates
1150:sulfite process
1146:
1144:Lignosulfonates
1108:
1092:water softening
1070:
1066:
1053:
1021:
1009:drilling fluids
982:
974:
967:
953:
944:
930:
921:
911:
902:
893:
884:
878:
869:
855:
837:
822:
815:
808:
796:
789:
773:
748:
736:
732:
728:
724:
720:
690:
659:
654:
643:
638:
617:
615:
612:
611:
583:
579:
569:
564:
545:
540:
535:
533:
530:
529:
509:
504:
496:
491:
483:
478:
465:
461:
454:
449:
440:
428:
423:
418:
416:
413:
412:
364:
359:
348:
343:
322:
317:
306:
304:
301:
300:
244:
239:
231:
226:
218:
213:
202:
197:
186:
181:
173:
168:
163:
161:
158:
157:
147:sulfur trioxide
128:
108:
104:
92:
88:
85:parent compound
64:
60:
48:
44:
17:
12:
11:
5:
3913:
3903:
3902:
3897:
3895:Sulfonic acids
3880:
3879:
3877:
3876:
3870:
3865:
3859:
3854:
3849:
3845:
3840:
3835:
3831:
3826:
3821:
3817:
3812:
3806:
3801:
3795:
3791:
3786:
3781:
3777:
3773:
3768:
3763:
3759:
3755:
3750:
3745:
3741:
3737:
3732:
3726:
3721:
3716:
3712:
3708:
3703:
3698:
3694:
3689:
3684:
3680:
3675:
3670:
3666:
3661:
3656:
3651:
3645:
3641:
3636:
3631:
3627:
3622:
3617:
3613:
3608:
3603:
3599:
3594:
3588:
3583:
3578:
3574:
3569:
3563:
3558:
3552:
3548:
3543:
3538:
3534:
3530:
3525:
3520:
3516:
3512:
3507:
3502:
3498:
3493:
3488:
3484:
3479:
3474:
3470:
3465:
3460:
3456:
3451:
3446:
3442:
3437:
3432:
3428:
3423:
3418:
3414:
3409:
3403:
3398:
3393:
3389:
3384:
3378:
3373:
3368:
3364:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3301:
3296:
3291:
3287:
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3213:
3208:
3203:
3199:
3194:
3189:
3185:
3181:
3174:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3069:
3064:
3058:
3053:
3048:
3043:
3038:
3034:
3029:
3024:
3020:
3014:
3011:
3010:
3003:
3002:
2995:
2988:
2980:
2971:
2970:
2968:
2967:
2966:
2965:
2960:
2948:
2941:
2935:
2932:
2931:
2929:
2928:
2926:Sulfinylamines
2923:
2918:
2913:
2908:
2906:Phosphoramides
2903:
2901:Isothiocyanate
2897:
2895:
2891:
2890:
2887:
2886:
2884:
2883:
2878:
2877:
2876:
2866:
2865:
2864:
2854:
2853:
2852:
2847:
2842:
2837:
2832:
2821:
2819:
2811:
2810:
2808:
2807:
2802:
2796:
2794:
2788:
2787:
2785:
2784:
2779:
2777:Selenenic acid
2774:
2772:Seleninic acid
2769:
2767:Selenonic acid
2764:
2758:
2756:
2750:
2749:
2747:
2746:
2741:
2735:
2733:
2727:
2726:
2724:
2723:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2647:
2646:
2636:
2630:
2628:
2622:
2621:
2619:
2618:
2613:
2608:
2603:
2602:
2601:
2591:
2586:
2581:
2576:
2575:
2574:
2564:
2563:
2562:
2560:Phosphodiester
2551:
2549:
2543:
2542:
2540:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2438:
2437:
2432:
2421:
2419:
2410:
2406:(one element,
2390:
2389:
2386:
2385:
2383:
2382:
2381:
2380:
2370:
2369:
2368:
2363:
2352:
2350:
2346:
2345:
2343:
2342:
2337:
2332:
2331:
2330:
2320:
2319:
2318:
2313:
2308:
2297:
2295:
2289:
2288:
2286:
2285:
2283:Methylenedioxy
2280:
2275:
2274:
2273:
2268:
2258:
2257:
2256:
2251:
2241:
2240:
2239:
2229:
2224:
2218:
2216:
2209:
2187:
2186:
2184:
2183:
2178:
2173:
2172:
2171:
2166:
2156:
2155:
2154:
2149:
2144:
2139:
2134:
2129:
2119:
2118:
2117:
2112:
2102:
2101:
2100:
2095:
2090:
2085:
2080:
2075:
2064:
2062:
2060:(only C and H)
2052:
2051:
2044:
2043:
2036:
2029:
2021:
2013:
2012:
1979:
1960:(2): 273–412.
1944:
1927:
1920:
1894:
1888:978-3527306732
1887:
1859:
1828:
1821:
1792:
1757:
1751:978-3527306732
1750:
1719:
1702:
1683:(3): 127–140.
1667:
1652:
1634:
1619:
1601:
1566:
1559:
1528:
1522:
1497:
1496:
1494:
1491:
1488:
1487:
1480:
1468:
1467:
1465:
1462:
1453:
1450:
1445:
1441:
1433:
1432:
1429:
1425:
1421:
1417:
1413:
1409:
1405:
1388:
1384:
1381:
1380:
1379:
1374:
1370:
1366:
1362:
1345:
1341:
1338:
1337:
1336:
1332:
1328:
1304:
1292:
1291:Esterification
1289:
1280:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1251:
1247:
1235:Main article:
1232:
1229:
1225:
1224:
1219:
1215:
1211:
1207:
1203:
1199:
1195:
1191:
1182:
1179:
1174:
1171:
1145:
1142:
1107:
1104:
1068:
1064:
1052:
1051:Acid catalysts
1049:
1020:
1017:
981:
978:
973:
970:
969:
968:
954:
947:
945:
931:
924:
922:
912:
905:
903:
894:
887:
885:
879:
872:
870:
856:
849:
847:
835:
820:
813:
806:
794:
787:
771:
747:
744:
734:
730:
726:
722:
717:carbyl sulfate
689:
686:
678:
677:
657:
649:
641:
631:
628:
623:
601:
600:
586:
578:
567:
559:
553:
548:
543:
527:
507:
494:
481:
473:
468:
460:
452:
443:
436:
431:
426:
383:
382:
362:
354:
346:
336:
333:
328:
320:
312:
286:sulfur dioxide
263:
262:
242:
229:
216:
208:
200:
192:
184:
171:
127:
124:
106:
101:sulfurous acid
90:
62:
59:group and the
46:
37:sulphonic acid
15:
9:
6:
4:
3:
2:
3912:
3901:
3898:
3896:
3893:
3892:
3890:
3875:
3866:
3864:
3855:
3853:
3841:
3839:
3827:
3825:
3813:
3811:
3802:
3800:
3787:
3785:
3769:
3767:
3751:
3749:
3733:
3731:
3722:
3720:
3704:
3702:
3690:
3688:
3676:
3674:
3662:
3660:
3657:
3655:
3652:
3650:
3637:
3635:
3623:
3621:
3609:
3607:
3595:
3593:
3584:
3582:
3570:
3568:
3559:
3557:
3544:
3542:
3526:
3524:
3508:
3506:
3494:
3492:
3480:
3478:
3466:
3464:
3452:
3450:
3438:
3436:
3424:
3422:
3410:
3408:
3399:
3397:
3385:
3383:
3374:
3372:
3356:
3354:
3346:
3344:
3336:
3334:
3331:
3329:
3326:
3324:
3316:
3314:
3311:
3309:
3297:
3295:
3283:
3281:
3273:
3271:
3263:
3261:
3253:
3251:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3209:
3207:
3195:
3193:
3166:
3164:
3161:
3159:
3156:
3154:
3146:
3144:
3136:
3134:
3126:
3124:
3121:
3119:
3116:
3114:
3106:
3104:
3096:
3094:
3086:
3084:
3081:
3079:
3076:
3074:
3065:
3063:
3054:
3052:
3049:
3047:
3044:
3042:
3030:
3028:
3016:
3015:
3012:
3008:
3001:
2996:
2994:
2989:
2987:
2982:
2981:
2978:
2964:
2961:
2959:
2956:
2955:
2954:
2953:
2949:
2947:
2946:
2942:
2937:
2936:
2933:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2898:
2896:
2892:
2882:
2879:
2875:
2872:
2871:
2870:
2867:
2863:
2860:
2859:
2858:
2855:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2827:
2826:
2823:
2822:
2820:
2818:
2817:
2812:
2806:
2805:Telluroketone
2803:
2801:
2798:
2797:
2795:
2793:
2789:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2759:
2757:
2755:
2751:
2745:
2742:
2740:
2737:
2736:
2734:
2732:
2728:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2691:Sulfonic acid
2689:
2687:
2684:
2682:
2681:Sulfinic acid
2679:
2677:
2676:Thiosulfonate
2674:
2672:
2669:
2667:
2666:Thiosulfinate
2664:
2662:
2661:Sulfenic acid
2659:
2657:
2654:
2652:
2649:
2645:
2642:
2641:
2640:
2637:
2635:
2632:
2631:
2629:
2627:
2623:
2617:
2616:Phosphaallene
2614:
2612:
2611:Phosphaalkyne
2609:
2607:
2606:Phosphaalkene
2604:
2600:
2597:
2596:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2573:
2570:
2569:
2568:
2565:
2561:
2558:
2557:
2556:
2553:
2552:
2550:
2548:
2544:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2436:
2433:
2431:
2428:
2427:
2426:
2423:
2422:
2420:
2418:
2414:
2411:
2391:
2379:
2376:
2375:
2374:
2371:
2367:
2364:
2362:
2359:
2358:
2357:
2354:
2353:
2351:
2347:
2341:
2338:
2336:
2333:
2329:
2326:
2325:
2324:
2321:
2317:
2314:
2312:
2309:
2307:
2304:
2303:
2302:
2299:
2298:
2296:
2294:
2290:
2284:
2281:
2279:
2278:Ethylenedioxy
2276:
2272:
2269:
2267:
2264:
2263:
2262:
2259:
2255:
2252:
2250:
2247:
2246:
2245:
2242:
2238:
2235:
2234:
2233:
2230:
2228:
2225:
2223:
2220:
2219:
2217:
2213:
2210:
2204:
2198:
2193:
2188:
2182:
2179:
2177:
2174:
2170:
2167:
2165:
2162:
2161:
2160:
2157:
2153:
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2124:
2123:
2120:
2116:
2113:
2111:
2108:
2107:
2106:
2103:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2079:
2076:
2074:
2071:
2070:
2069:
2066:
2065:
2063:
2057:
2053:
2049:
2042:
2037:
2035:
2030:
2028:
2023:
2022:
2019:
2007:
2002:
1998:
1994:
1990:
1983:
1975:
1971:
1967:
1963:
1959:
1955:
1948:
1941:
1937:
1931:
1923:
1917:
1913:
1909:
1905:
1898:
1890:
1884:
1880:
1876:
1872:
1871:
1863:
1855:
1851:
1847:
1843:
1839:
1832:
1824:
1818:
1814:
1810:
1806:
1799:
1797:
1788:
1784:
1780:
1776:
1772:
1768:
1761:
1753:
1747:
1743:
1739:
1735:
1734:
1726:
1724:
1716:
1712:
1706:
1698:
1694:
1690:
1686:
1682:
1678:
1671:
1663:
1659:
1655:
1649:
1645:
1638:
1630:
1626:
1622:
1616:
1612:
1605:
1597:
1593:
1589:
1585:
1581:
1577:
1570:
1562:
1560:3-527-30673-0
1556:
1552:
1548:
1544:
1543:
1535:
1533:
1525:
1523:0-471-60180-2
1519:
1515:
1511:
1505:
1503:
1498:
1473:
1469:
1461:
1459:
1449:
1439:
1416:Na + NaOH → C
1403:
1402:
1401:
1399:
1395:
1359:
1358:
1357:
1355:
1351:
1326:
1325:
1324:
1322:
1318:
1314:
1310:
1302:
1298:
1288:
1286:
1244:
1243:
1242:
1238:
1228:
1188:
1187:
1186:
1178:
1166:
1162:
1160:
1156:
1151:
1138:
1133:
1129:
1127:
1120:
1116:
1112:
1103:
1101:
1097:
1093:
1089:
1085:
1081:
1077:
1075:
1062:
1058:
1048:
1046:
1042:
1038:
1034:
1033:carbohydrates
1030:
1026:
1025:anthraquinone
1016:
1014:
1010:
1006:
1002:
998:
994:
990:
986:
977:
965:
961:
957:
951:
946:
942:
938:
934:
928:
923:
919:
915:
909:
904:
900:
898:
891:
886:
882:
876:
871:
867:
863:
859:
853:
848:
845:
844:
843:
841:
840:sulfuric acid
833:
828:
824:
819:
812:
804:
800:
793:
786:
782:
778:
774:
770:
764:
760:
758:
753:
743:
741:
718:
714:
710:
708:
707:Reed reaction
703:
699:
695:
685:
683:
655:
639:
629:
626:
621:
610:
609:
608:
606:
584:
576:
565:
551:
546:
541:
528:
505:
492:
479:
466:
458:
450:
441:
434:
429:
424:
411:
410:
409:
407:
406:alkyl halides
403:
399:
394:
392:
388:
360:
344:
334:
331:
326:
318:
310:
299:
298:
297:
295:
291:
287:
283:
282:sulfoxidation
278:
276:
272:
268:
240:
227:
214:
198:
190:
182:
169:
156:
155:
154:
152:
148:
144:
136:
132:
123:
121:
117:
113:
102:
98:
86:
82:
78:
77:sulfuric acid
74:
70:
58:
54:
42:
38:
34:
33:sulfonic acid
30:
21:
3869:H[Co(CO)
2950:
2943:
2857:Vinyl halide
2814:
2744:Borinic acid
2739:Boronic acid
2716:Thioxanthate
2690:
2056:Hydrocarbons
1996:
1992:
1982:
1957:
1953:
1947:
1930:
1903:
1897:
1868:
1862:
1845:
1841:
1837:
1831:
1804:
1770:
1766:
1760:
1731:
1705:
1680:
1676:
1670:
1643:
1637:
1610:
1604:
1579:
1575:
1569:
1540:
1513:
1510:March, Jerry
1472:
1455:
1452:o-Lithiation
1434:
1386:
1343:
1340:Halogenation
1294:
1281:
1240:
1226:
1184:
1176:
1147:
1124:
1073:
1054:
1022:
983:
975:
972:Applications
896:
829:
825:
817:
810:
791:
784:
777:benzoic acid
768:
756:
749:
711:
691:
679:
602:
395:
384:
279:
267:electrophile
264:
140:
72:
36:
32:
26:
2921:Thiocyanate
2916:Sulfonamide
2881:Perchlorate
2869:Acyl halide
2830:Fluoroethyl
2711:Thionoester
2599:Phosphonium
2584:Phosphinate
2579:Phosphonous
2567:Phosphonate
2266:Hydroperoxy
2088:Cyclopropyl
1321:alcoholysis
1126:Sulfa drugs
1115:Acamprosate
1088:polystyrene
997:fatty acids
989:surfactants
964:natural gas
962:, found in
781:acetic acid
294:surfactants
143:sulfonation
126:Preparation
81:substituent
73:sulfo group
3889:Categories
2825:Haloalkane
2696:Thioketone
2651:Persulfide
2547:Phosphorus
2512:Isocyanate
2502:Isonitrile
2403:or oxygen
2401:hydrogen,
2397:not being
2378:Orthoester
2271:Dioxiranes
2249:Enol ether
2137:1-Propenyl
1840:-Cresol".
1493:References
1100:fuel cells
985:Detergents
956:Coenzyme-M
937:surfactant
918:fuel cells
752:carboxylic
746:Properties
120:sulfonates
3551:[PtCl
2958:inorganic
2792:Tellurium
2706:Thioester
2671:Sulfoxide
2656:Disulfide
2644:Sulfonium
2594:Phosphine
2572:Phosphite
2555:Phosphate
2487:Carbamate
2462:Hydrazone
2395:element,
2393:Only one
2366:Anhydride
2105:Methylene
1974:0009-2665
1767:Chem. Rev
1697:1463-9262
1662:867050415
1629:708034394
1596:0001-4842
1335:OR′ + HCl
1262:O → R−C
1173:Reactions
1157:, useful
1057:catalysts
862:bile acid
823:= −5.9).
809:, whose p
803:sulfonate
648:⟶
585:−
558:⟶
547:−
472:⟶
430:−
402:alkylated
398:bisulfite
353:⟶
207:⟶
105:S(=O)(OH)
3644:[SiF
3068:H[BF
2939:See also
2874:Chloride
2800:Tellurol
2754:Selenium
2721:Xanthate
2435:Ammonium
2417:Nitrogen
2399:carbon,
2356:Carboxyl
2323:Aldehyde
2311:Acryloyl
2293:carbonyl
2197:hydrogen
2152:Cumulene
1787:17973436
1512:(1992),
1377:F + HF
1369:H → SOF
1159:ionomers
1041:sulfonyl
1029:proteins
1013:concrete
939:used in
866:tautomer
740:ethylene
269:and the
97:tautomer
69:sulfonyl
67:group a
2963:organic
2762:Selenol
2686:Sulfone
2639:Sulfide
2537:NONOate
2532:Nitroso
2522:Nitrite
2517:Nitrate
2507:Cyanate
2497:Nitrile
2482:Amidine
2477:Imidate
2447:Nitrene
2442:Hydrazo
2430:Enamine
2361:Acetoxy
2349:carboxy
2316:Benzoyl
2254:Epoxide
2237:Methoxy
2227:Alcohol
2181:Carbene
2115:Methine
1438:benzyne
1424:OH + Na
1210:OH + Na
1148:In the
1071:OH and
960:methane
858:Taurine
682:taurine
45:R−S(=O)
2862:Iodide
2782:Selone
2626:Sulfur
2335:Ketone
2328:Ketene
2306:Acetyl
2261:Peroxy
2232:Alkoxy
2222:Acetal
2203:oxygen
2192:carbon
2176:Alkyne
2169:Benzyl
2164:Phenyl
2147:Allene
2142:Crotyl
2122:Alkene
2110:Bridge
2098:Pentyl
2083:Propyl
2073:Methyl
1972:
1918:
1885:
1848:: 37.
1819:
1785:
1748:
1695:
1660:
1650:
1627:
1617:
1594:
1557:
1520:
1479:HS(=O)
1394:phenol
1297:esters
1096:Nafion
1005:lignin
914:Nafion
605:thiols
290:oxygen
116:esters
89:HS(=O)
83:. The
3319:NaHCO
2894:Other
2731:Boron
2701:Thial
2634:Thiol
2527:Nitro
2492:Imide
2472:Amide
2457:Oxime
2452:Imine
2425:Amine
2373:Ester
2340:Ynone
2244:Ether
2215:R-O-R
2190:Only
2132:Allyl
2127:Vinyl
2093:Butyl
2078:Ethyl
2068:Alkyl
1464:Notes
1373:+ RSO
1365:+ RSO
1258:H + H
1106:Drugs
1084:Dowex
993:soaps
765:have
271:arene
112:Salts
61:S(=O)
53:alkyl
3659:HNCS
3654:HSCN
3328:HNCO
3276:HMnO
3163:HCNO
3149:HClO
3139:HClO
3129:HClO
3123:HClO
3109:HBrO
3099:HBrO
3089:HBrO
3083:HBrO
3046:HArF
2816:Halo
2301:Acyl
2201:and
2159:Aryl
1970:ISSN
1916:ISBN
1883:ISBN
1817:ISBN
1783:PMID
1746:ISBN
1693:ISSN
1658:OCLC
1648:ISBN
1625:OCLC
1615:ISBN
1592:ISSN
1555:ISBN
1518:ISBN
1063:, CH
1037:dyes
1031:and
1019:Dyes
987:and
881:PFOS
860:, a
799:salt
779:and
761:and
288:and
95:, a
93:(OH)
65:(OH)
57:aryl
35:(or
3848:TiO
3834:TeO
3820:TeO
3630:SiO
3616:SeO
3602:SeO
3392:NSO
3377:HNO
3349:HNO
3339:HNO
3333:HNO
3313:HNC
3304:MoO
3290:MnO
3266:HIO
3256:HIO
3246:HIO
3240:HIO
3230:HFO
3173:CrO
3158:HCN
3118:HCl
3078:HBr
3057:HSO
3051:HAt
3037:AsO
3023:AsO
2467:Azo
2001:doi
1962:doi
1936:doi
1908:doi
1875:doi
1850:doi
1809:doi
1775:doi
1771:107
1738:doi
1711:doi
1685:doi
1584:doi
1547:doi
1327:RSO
1315:in
1270:+ H
1246:R−C
1218:+ H
1094:).
807:(g)
729:(SO
719:, (
652:RSO
619:RSH
562:RSO
555:RBr
538:HSO
476:RCH
438:RCH
421:HSO
404:by
389:to
357:RSO
277:.
114:or
99:of
55:or
49:−OH
27:In
3891::
3862:Po
3809:Te
3794:SO
3790:CF
3697:SO
3683:SO
3669:SO
3591:Se
3539:10
3501:PO
3487:PO
3473:PO
3235:HI
3225:HF
3216:CS
3202:CO
3184:Cr
2199:,
2194:,
1997:39
1995:.
1991:.
1968:.
1958:49
1956:.
1914:.
1881:.
1844:.
1815:.
1795:^
1781:.
1769:.
1744:.
1722:^
1691:.
1679:.
1656:.
1623:.
1590:.
1580:21
1578:.
1553:.
1531:^
1501:^
1428:SO
1412:SO
1361:SF
1356::
1274:SO
1254:SO
1214:SO
1198:SO
1102:.
1067:SO
1015:.
868:).
842:.
742:.
709:.
684:.
607::
581:Br
502:SO
489:CH
447:CH
408::
393:.
315:SO
308:RH
296:.
237:SO
211:RC
195:SO
166:RC
153::
122:.
110:.
103:,
31:,
3873:]
3871:4
3860:2
3858:H
3850:4
3846:4
3844:H
3836:6
3832:6
3830:H
3822:3
3818:2
3816:H
3807:2
3805:H
3798:H
3796:3
3792:3
3782:8
3780:O
3778:2
3776:S
3774:2
3772:H
3764:7
3762:O
3760:2
3758:S
3756:2
3754:H
3746:6
3744:O
3742:2
3740:S
3738:2
3736:H
3729:O
3727:3
3725:H
3717:3
3715:O
3713:2
3711:S
3709:2
3707:H
3699:5
3695:2
3693:H
3685:4
3681:2
3679:H
3671:3
3667:2
3665:H
3648:]
3646:6
3642:2
3640:H
3632:4
3628:4
3626:H
3618:4
3614:2
3612:H
3604:3
3600:2
3598:H
3589:2
3587:H
3579:2
3577:S
3575:2
3573:H
3566:S
3564:2
3562:H
3555:]
3553:6
3549:2
3547:H
3537:O
3535:3
3533:P
3531:5
3529:H
3521:7
3519:O
3517:2
3515:P
3513:4
3511:H
3503:4
3499:3
3497:H
3489:3
3485:3
3483:H
3475:2
3471:3
3469:H
3461:5
3459:O
3457:2
3455:H
3447:4
3445:O
3443:2
3441:H
3433:3
3431:O
3429:2
3427:H
3419:2
3417:O
3415:2
3413:H
3406:O
3404:2
3402:H
3394:3
3390:3
3388:H
3381:S
3379:5
3369:2
3367:O
3365:2
3363:N
3361:2
3359:H
3351:3
3341:2
3321:3
3306:4
3302:2
3300:H
3292:4
3288:2
3286:H
3278:4
3268:4
3258:3
3248:2
3218:3
3214:2
3212:H
3204:3
3200:2
3198:H
3190:7
3188:O
3186:2
3182:2
3180:H
3178:/
3175:4
3171:2
3169:H
3151:4
3141:3
3131:2
3111:4
3101:3
3091:2
3072:]
3070:4
3061:F
3059:3
3039:4
3035:3
3033:H
3025:3
3021:3
3019:H
2999:e
2992:t
2985:v
2040:e
2033:t
2026:v
2009:.
2003::
1976:.
1964::
1942:.
1938::
1924:.
1910::
1891:.
1877::
1856:.
1852::
1846:3
1838:p
1825:.
1811::
1789:.
1777::
1754:.
1740::
1717:.
1713::
1699:.
1687::
1681:1
1664:.
1631:.
1598:.
1586::
1563:.
1549::
1485:.
1481:2
1446:2
1442:N
1436:(
1430:3
1426:2
1422:5
1420:H
1418:6
1414:3
1410:5
1408:H
1406:6
1404:C
1389:3
1375:2
1371:2
1367:3
1363:4
1346:2
1333:2
1329:2
1305:2
1276:4
1272:2
1268:5
1266:H
1264:6
1260:2
1256:3
1252:4
1250:H
1248:6
1222:O
1220:2
1216:3
1212:2
1208:5
1206:H
1204:6
1200:3
1196:5
1194:H
1192:6
1190:C
1121:.
1074:p
1069:2
1065:3
966:.
943:.
920:.
897:p
836:2
821:a
818:K
814:a
811:K
795:a
792:K
788:a
785:K
772:a
769:K
767:p
757:p
735:2
733:)
731:3
727:4
725:H
723:2
721:C
664:H
656:3
640:2
636:O
630:2
627:3
622:+
577:+
574:H
566:3
552:+
542:3
514:H
506:3
493:2
480:2
467:+
463:H
459:+
451:2
442:=
435:+
425:3
369:H
361:3
345:2
341:O
335:2
332:1
327:+
319:2
311:+
249:H
241:3
228:4
224:H
215:6
199:3
191:+
183:5
179:H
170:6
107:2
91:2
63:2
47:2
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