938:
886:
961:
31:
142:
863:
1122:
901:
1176:
919:
1143:
1293:
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
837:
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
1163:
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
1446:
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
1402:
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
715:
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
1487:
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:
536:
849:
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
609:
391:
937:
271:
686:
801:
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
1298:, 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.
862:
960:
1455:
Ar mechanism, as revealed by a C labeling, despite the lack of stabilizing substituents. Sulfonic acids with electron-withdrawing groups (e.g., with NO
1880:
1743:
1552:
1010:. Since the mid-20th century, the usage of sulfonic acids has surpassed soap in advanced societies. For example, an estimated 2 billion kilograms of
885:
3008:
2049:
900:
2968:
425:
2973:
1945:
Manfred Weber, Markus Weber, Michael Kleine-Boymann "Phenol" in
Ullmann's Encyclopedia of Industrial Chemistry 2004, Wiley-VCH.
808:
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 (
1930:
1831:
1662:
1629:
987:
Both alkyl and aryl sulfonic acids are known, most large-scale applications are associated with the aromatic derivatives.
918:
761:
Sulfonic acids are strong acids. They are commonly cited as being around a million times stronger than the corresponding
542:
313:
285:
17:
170:
1897:
1760:
1686:
Gernon, Michael D.; Wu, Min; Buszta, Thomas; Janney, Patrick (1999). "Environmental benefits of methanesulfonic acid".
1569:
1532:
624:
3001:
2042:
1294:
group, as illustrated by the purification of para-xylene via its sulfonic acid derivative. In the synthesis of
943:
816:
and hydrogen chloride. This property implies an acidity within two or three orders of magnitude of that of HCl
1913:
Boswell, G. A.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. (2011). "Fluorination by Sulfur
Tetrafluoride".
2872:
3878:
708:
2994:
1814:
Tanaka, Kazuhiko (1991). "Sulfonic Acids, Esters, Amides and
Halides as Synthons". In Saul Patai (ed.).
3910:
2445:
2035:
1720:
Kosswig, K. "Surfactants" in
Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.
777:
1093:
as acids that are lipophilic (soluble in organic solvents). Polymeric sulfonic acids are also useful.
1741:
Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2002). "Anthraquinone Dyes and
Intermediates".
838:
short-chain sulfonic acids water-soluble, while longer-chain ones exhibit detergent-like properties.
161:
1963:
Bunnett, Joseph F.; Zahler, Roland E. (1951-10-01). "Aromatic
Nucleophilic Substitution Reactions".
1467:
Arylsulfonic acids react with two equiv of butyl lithium to give the ortho-lithio derivatives, i.e.
2482:
396:
Direct reaction of alkanes with sulfur trioxide is not generally useful, except for the conversion
3905:
3702:
2955:
3649:
2855:
1247:
1136:
1083:
1055:
906:
766:
401:
51:
3781:
3386:
2962:
2850:
1188:
The reactivity of the sulfonic acid group is so extensive that it is difficult to summarize.
1011:
303:. This reaction is employed industrially to produce alkyl sulfonic acids, which are used as
794:
are 4.20 and 4.76, respectively. However, as a consequence of their strong acidity, their p
3478:
2931:
2376:
1364:
1252:
Arylsulfonic acids are susceptible to hydrolysis, the reverse of the sulfonation reaction:
1129:
1071:
842:
773:
397:
145:
1014:
are produced annually for diverse purposes. Lignin sulfonates, produced by sulfonation of
8:
3556:
3520:
3411:
3323:
3066:
3056:
2237:
1147:
712:
3814:
3669:
3582:
3538:
3328:
3017:
1585:
Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution".
1295:
1109:, a fluorinated polymeric sulfonic acid is a component of proton exchange membranes in
1038:
dyes are produced or processed via sulfonation. Sulfonic acids tend to bind tightly to
723:
30:
711:
is prepared by hydrolysis of the sulfonyl fluoride, which in turn is generated by the
3734:
3716:
3596:
3422:
3240:
3235:
3221:
3133:
3128:
3061:
2921:
2891:
2649:
2271:
1980:
1926:
1893:
1827:
1793:
1756:
1703:
1668:
1658:
1635:
1625:
1602:
1565:
1528:
1327:
1090:
951:
39:
1196:
When treated with strong base, benzenesulfonic acid derivatives convert to phenols.
3867:
3571:
3492:
3368:
3285:
3168:
3093:
3088:
3077:
2626:
2120:
2058:
2011:
1972:
1946:
1918:
1885:
1878:
Otto
Lindner; Lars Rodefeld (2005). "Benzenesulfonic Acids and Their Derivatives".
1860:
1819:
1785:
1748:
1721:
1695:
1594:
1557:
1468:
1408:
1360:
1323:
1311:
1002:
are molecules that combine highly nonpolar and highly polar groups. Traditionally,
122:
1950:
3763:
3664:
3506:
3250:
3245:
3158:
2845:
2604:
2599:
2582:
2565:
2366:
2115:
1319:
1160:
1102:
809:
704:
157:
98:(with the organic substituent replaced by hydrogen) is the parent sulfonic acid,
95:
1998:
Oae, Shigeru; Furukawa, Naomichi; Kise, Masahiro; Kawanishi, Mitsuyoshi (1966).
1922:
141:
34:
General structure of a sulfonic acid with the functional group indicated in blue
3825:
3745:
3674:
3338:
3118:
2916:
2911:
2787:
2782:
2777:
2570:
2537:
2321:
2303:
2293:
1165:
1019:
727:
296:
111:
1471:. These dilithio compounds are poised for reactions with many electrophiles.
3899:
3839:
3688:
3607:
3397:
3309:
3295:
3275:
3207:
3173:
3138:
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2517:
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2288:
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2125:
1984:
1889:
1864:
1752:
1725:
1707:
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1639:
1606:
1561:
1035:
850:
717:
292:
87:
1823:
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3621:
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3450:
3348:
3178:
3148:
3098:
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2754:
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2726:
2477:
2316:
2242:
2179:
2174:
2152:
2108:
2093:
2083:
1797:
1776:
Busca, Guido (2007). "Acid
Catalysts in Industrial Hydrocarbon Chemistry".
1451:
mechanism), benzenesulfonic acid undergoes the analogous conversion by an S
1043:
875:, and one of the few naturally occurring sulfonic acids (shown in uncommon
787:
416:
277:
3358:
3255:
3108:
2926:
2879:
2840:
2721:
2609:
2594:
2589:
2577:
2142:
2137:
2103:
2098:
2088:
2066:
2016:
1999:
1520:
1331:
1125:
1098:
974:
791:
153:
91:
1976:
1622:
March's advanced organic chemistry: reactions, mechanisms, and structure
1598:
1121:
3436:
3265:
2835:
2826:
2706:
2661:
2557:
2522:
2512:
2452:
2388:
2311:
2259:
1175:
1007:
999:
966:
947:
412:
304:
1789:
1172:, which are soluble and can be separated from the cellulose fibers.
2986:
2802:
2716:
2681:
2666:
2654:
2497:
2472:
2281:
1699:
1363:. Sulfonyl fluorides can be produced by treating sulfonic acids with
1110:
995:
928:
872:
813:
408:
130:
2027:
1653:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart G. (January 2012).
1238:
In this case the sulfonate behaves as a pseudohalide leaving group.
1179:
idealized scheme for lignin depolymerization by the
Sulfite process.
1142:
3343:
2810:
2764:
2731:
2427:
2333:
2207:
2162:
2147:
1459:
or CN substituents) undergo this transformation much more readily.
1067:
1051:
1023:
876:
762:
750:
749:), which in turn is obtained by the addition of sulfur trioxide to
107:
79:
2772:
2696:
2547:
2542:
2507:
2492:
2487:
2457:
2440:
2264:
2191:
2157:
1448:
1169:
1039:
970:
868:
841:
The structure of sulfonic acids is illustrated by the prototype,
692:
1525:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
160:. A large scale application of this method is the production of
2860:
2792:
2636:
2345:
2338:
2232:
2213:
2202:
2186:
2132:
1404:
1139:, a class of antibacterials, are produced from sulfonic acids.
1106:
1015:
924:
300:
2000:"The Mechanism of the Alkaline Fusion of Benzenesulfonic Acid"
531:{\displaystyle {\ce {HSO3- + RCH=CH2 + H+ -> RCH2CH2SO3H}}}
407:
Many alkane sulfonic acids can be obtained by the addition of
2741:
2711:
2644:
2502:
2467:
2462:
2435:
2383:
2350:
2254:
2078:
1307:
1094:
615:
281:
126:
63:
1818:. PATAI'S Chemistry of Functional Groups. pp. 401–452.
2169:
1912:
1003:
891:
67:
1877:
1359:−X) are produced by chlorination of sulfonic acids using
1047:
671:
655:
581:
521:
508:
495:
466:
376:
360:
334:
256:
243:
230:
214:
198:
185:
1997:
291:
Alkylsulfonic acids can be prepared by many methods. In
786:
values of −2.8 and −1.9, respectively, while those of
635:
340:
1740:
627:
604:{\displaystyle {\ce {HSO3- + RBr -> RSO3H + Br-}}}
545:
428:
386:{\displaystyle {\ce {RH + SO2 + 1/2 O2 -> RSO3H}}}
316:
173:
1816:
Sulphonic Acids, Esters and their Derivatives (1991)
1685:
1652:
1066:
Being strong acids, sulfonic acids are also used as
1624:(6th ed.). Hoboken, N.J.: Wiley-Interscience.
1550:Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic".
284:is the nucleophile. The reaction is an example of
266:{\displaystyle {\ce {RC6H5 + SO3 -> RC6H4SO3H}}}
152:Aryl sulfonic acids are produced by the process of
703:Many sulfonic acids are prepared by hydrolysis of
680:
603:
530:
385:
265:
1657:(2nd ed.). Oxford: Oxford University Press.
969:, is a cofactor required for the biosynthesis of
691:This pathway is the basis of the biosynthesis of
3897:
1128:is a sulfonic acid-containing drug use to treat
1006:are the popular surfactants, being derived from
681:{\displaystyle {\ce {RSH + 3/2 O2 -> RSO3H}}}
27:Organic compounds with the structure R−S(=O)2−OH
1411:, which can be generated readily from benzene.
1101:and is used as catalysts and for ion exchange (
614:Sulfonic acids can be prepared by oxidation of
90:with one hydroxyl group replaced by an organic
1881:Ullmann's Encyclopedia of Industrial Chemistry
1744:Ullmann's Encyclopedia of Industrial Chemistry
1553:Ullmann's Encyclopedia of Industrial Chemistry
1330:. Such sulfonate esters are often prepared by
82:hydroxide. As a substituent, it is known as a
3002:
2043:
1962:
1846:
990:
912:, a widely used reagent in organic synthesis.
894:, a surfactant and a controversial pollutant.
1736:
1734:
1519:
1393:
857:Representative sulfonic acids and sulfonates
411:to terminal alkenes. Bisulfite can also be
1241:
1050:are sulfonic acids (or have the functional
295:, alkanes are irradiated with a mixture of
3009:
2995:
2050:
2036:
1619:
2015:
2004:Bulletin of the Chemical Society of Japan
1731:
1809:
1807:
1584:
1191:
1174:
1141:
1120:
276:In this reaction, sulfur trioxide is an
140:
86:. A sulfonic acid can be thought of as
29:
1939:
1906:
1549:
1515:
1513:
1407:involved the base hydrolysis of sodium
1097:resin are sulfonic acid derivatives of
14:
3898:
3016:
1813:
1545:
1543:
927:, a polymeric sulfonic acid useful in
2990:
2057:
2031:
1804:
1775:
1620:Smith, Michael; March, Jerry (2007).
827:was recently accurately determined (p
50:) refers to a member of the class of
1510:
698:
1540:
1306:Sulfonic acids can be converted to
286:electrophilic aromatic substitution
156:. Usually the sulfonating agent is
24:
1154:
1022:and additives in certain kinds of
25:
3922:
1527:(4th ed.), New York: Wiley,
1301:
1146:Sulfonates are the basis of most
1061:
1054:group in them) for this reason.
959:
936:
917:
899:
884:
861:
1991:
1956:
1871:
1840:
1769:
1462:
1398:Although strong, the (aryl)C−SO
1350:
982:
707:and related precursors. Thus,
1714:
1679:
1646:
1613:
1578:
1481:
1089:, which are regularly used in
944:Sodium dodecylbenzenesulfonate
845:. The sulfonic acid group, RSO
658:
568:
482:
363:
217:
136:
13:
1:
1951:10.1002/14356007.a19_299.pub2
1587:Accounts of Chemical Research
1503:
1318:−OR. Sulfonic esters such as
756:
129:of sulfonic acids are called
1355:Sulfonyl halide groups (R−SO
1314:has the general formula R−SO
1183:
1070:. The simplest examples are
726:is derived by hydrolysis of
709:perfluorooctanesulfonic acid
7:
1923:10.1002/0471264180.or021.01
1334:of the sulfonyl chlorides:
1058:is used to make food dyes.
946:, an alkylbenzenesulfonate
10:
3927:
1245:
991:Detergents and surfactants
162:alkylbenzenesulfonic acids
3024:
2945:
2904:
2824:
2801:
2763:
2740:
2635:
2556:
2426:
2403:
2359:
2302:
2225:
2200:
2065:
1394:Displacement by hydroxide
54:with the general formula
1890:10.1002/14356007.a03_507
1865:10.15227/orgsyn.003.0037
1753:10.1002/14356007.a02_355
1726:10.1002/14356007.a25_747
1562:10.1002/14356007.a25_503
1474:
1242:Hydrolytic desulfonation
1150:used in water softening.
1116:
1056:p-Cresidinesulfonic acid
1034:Many if not most of the
148:of methanesulfonic acid.
62:, where R is an organic
2956:chemical classification
1884:. Weinheim: Wiley-VCH.
1847:W. W. Hartman (1923). "
1824:10.1002/0470034394.ch11
1747:. Weinheim: Wiley-VCH.
1556:. Weinheim: Wiley-VCH.
1029:
1248:Desulfonation reaction
1180:
1151:
1133:
1012:alkylbenzenesulfonates
682:
605:
532:
402:methanedisulfonic acid
387:
267:
149:
52:organosulfur compounds
35:
2963:chemical nomenclature
1192:Hydrolysis to phenols
1178:
1145:
1124:
1087:-toluenesulfonic acid
910:-Toluenesulfonic acid
812:) to form the sodium
770:-Toluenesulfonic acid
683:
606:
533:
388:
268:
144:
33:
2017:10.1246/bcsj.39.1212
1365:sulfur tetrafluoride
1322:are considered good
1130:alcohol use disorder
1072:methanesulfonic acid
843:methanesulfonic acid
774:methanesulfonic acid
625:
543:
426:
398:methanesulfonic acid
314:
171:
146:Ball-and-stick model
2419:not C, H or O)
1977:10.1021/cr60153a002
1599:10.1021/ar00156a004
1148:ion exchange resins
765:acid. For example,
713:electrofluorination
673:
657:
583:
561:
523:
510:
497:
468:
444:
378:
362:
336:
258:
245:
232:
216:
200:
187:
18:Alkyl sulfonic acid
3018:Hydrogen compounds
2861:Hypervalent iodine
1917:. pp. 1–124.
1494:(O) ⇌ S(=O)(OH)(O)
1296:2,6-dichlorophenol
1181:
1152:
1134:
1046:. Most "washable"
1018:are components of
952:laundry detergents
724:Vinylsulfonic acid
678:
661:
645:
644:
601:
571:
547:
528:
511:
498:
485:
456:
430:
383:
366:
350:
349:
324:
263:
246:
233:
220:
204:
188:
175:
150:
36:
3911:Functional groups
3893:
3892:
2984:
2983:
2922:Sulfenyl chloride
2900:
2899:
2399:
2398:
2218:(only C, H and O)
2059:Functional groups
1932:978-0-471-26418-7
1915:Organic Reactions
1853:Organic Syntheses
1833:978-0-470-03439-2
1790:10.1021/cr068042e
1784:(11): 5366–5410.
1664:978-0-19-166621-6
1655:Organic chemistry
1631:978-1-61583-842-4
1328:organic synthesis
1324:alkylating agents
1312:organic compounds
1091:organic chemistry
699:Hydrolysis routes
676:
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40:organic chemistry
16:(Redirected from
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2856:Trifluoromethoxy
2424:
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2045:
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2028:
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2019:
2010:(6): 1212–1216.
1995:
1989:
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1965:Chemical Reviews
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1576:
1575:
1547:
1538:
1537:
1517:
1497:
1495:
1485:
1469:ortho-lithiation
1409:benzenesulfonate
1389:
1361:thionyl chloride
1310:. This class of
1289:
1234:
1213:H + 2 NaOH → C
963:
940:
921:
903:
888:
865:
748:
705:sulfonyl halides
687:
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183:
176:
120:
105:
77:
61:
21:
3926:
3925:
3921:
3920:
3919:
3917:
3916:
3915:
3896:
3895:
3894:
3889:
3883:
3879:
3872:
3868:
3862:
3858:
3854:
3848:
3844:
3840:
3834:
3830:
3826:
3819:
3815:
3808:
3804:
3800:
3794:
3790:
3786:
3782:
3776:
3772:
3768:
3764:
3758:
3754:
3750:
3746:
3739:
3735:
3729:
3725:
3721:
3717:
3711:
3707:
3703:
3697:
3693:
3689:
3683:
3679:
3675:
3658:
3654:
3650:
3644:
3640:
3636:
3630:
3626:
3622:
3616:
3612:
3608:
3601:
3597:
3591:
3587:
3583:
3576:
3572:
3565:
3561:
3557:
3551:
3547:
3543:
3539:
3533:
3529:
3525:
3521:
3515:
3511:
3507:
3501:
3497:
3493:
3487:
3483:
3479:
3473:
3469:
3465:
3459:
3455:
3451:
3445:
3441:
3437:
3431:
3427:
3423:
3416:
3412:
3406:
3402:
3398:
3391:
3387:
3381:
3377:
3373:
3369:
3363:
3359:
3353:
3349:
3333:
3329:
3318:
3314:
3310:
3304:
3300:
3296:
3290:
3286:
3280:
3276:
3270:
3266:
3260:
3256:
3230:
3226:
3222:
3216:
3212:
3208:
3202:
3198:
3194:
3190:
3187:
3183:
3179:
3163:
3159:
3153:
3149:
3143:
3139:
3123:
3119:
3113:
3109:
3103:
3099:
3082:
3078:
3071:
3067:
3051:
3047:
3043:
3037:
3033:
3029:
3020:
3015:
2985:
2980:
2949:
2941:
2896:
2851:Trichloromethyl
2846:Trifluoromethyl
2820:
2797:
2759:
2736:
2631:
2600:Phosphine oxide
2552:
2418:
2416:
2415:
2413:
2411:
2409:
2407:
2405:
2395:
2355:
2298:
2217:
2216:
2211:
2206:
2196:
2070:
2069:
2061:
2056:
2026:
2025:
1996:
1992:
1961:
1957:
1944:
1940:
1933:
1911:
1907:
1900:
1876:
1872:
1845:
1841:
1834:
1812:
1805:
1774:
1770:
1763:
1739:
1732:
1719:
1715:
1688:Green Chemistry
1684:
1680:
1665:
1651:
1647:
1632:
1618:
1614:
1593:(12): 456–463.
1583:
1579:
1572:
1548:
1541:
1535:
1518:
1511:
1506:
1501:
1500:
1493:
1489:
1486:
1482:
1477:
1465:
1458:
1454:
1442:
1438:
1434:
1430:
1426:
1422:
1418:
1401:
1396:
1387:
1383:
1379:
1375:
1371:
1358:
1353:
1345:
1342:Cl + R′OH → RSO
1341:
1320:methyl triflate
1317:
1304:
1288:
1284:
1280:
1276:
1272:
1268:
1264:
1260:
1256:
1250:
1244:
1232:
1228:
1224:
1220:
1216:
1212:
1208:
1204:
1200:
1194:
1186:
1166:lignosulfonates
1161:sulfite process
1157:
1155:Lignosulfonates
1119:
1103:water softening
1081:
1077:
1064:
1032:
1020:drilling fluids
993:
985:
978:
964:
955:
941:
932:
922:
913:
904:
895:
889:
880:
866:
848:
833:
826:
819:
807:
800:
784:
759:
747:
743:
739:
735:
731:
701:
670:
665:
654:
649:
628:
626:
623:
622:
594:
590:
580:
575:
556:
551:
546:
544:
541:
540:
520:
515:
507:
502:
494:
489:
476:
472:
465:
460:
451:
439:
434:
429:
427:
424:
423:
375:
370:
359:
354:
333:
328:
317:
315:
312:
311:
255:
250:
242:
237:
229:
224:
213:
208:
197:
192:
184:
179:
174:
172:
169:
168:
158:sulfur trioxide
139:
119:
115:
103:
99:
96:parent compound
75:
71:
59:
55:
28:
23:
22:
15:
12:
11:
5:
3924:
3914:
3913:
3908:
3906:Sulfonic acids
3891:
3890:
3888:
3887:
3881:
3876:
3870:
3865:
3860:
3856:
3851:
3846:
3842:
3837:
3832:
3828:
3823:
3817:
3812:
3806:
3802:
3797:
3792:
3788:
3784:
3779:
3774:
3770:
3766:
3761:
3756:
3752:
3748:
3743:
3737:
3732:
3727:
3723:
3719:
3714:
3709:
3705:
3700:
3695:
3691:
3686:
3681:
3677:
3672:
3667:
3662:
3656:
3652:
3647:
3642:
3638:
3633:
3628:
3624:
3619:
3614:
3610:
3605:
3599:
3594:
3589:
3585:
3580:
3574:
3569:
3563:
3559:
3554:
3549:
3545:
3541:
3536:
3531:
3527:
3523:
3518:
3513:
3509:
3504:
3499:
3495:
3490:
3485:
3481:
3476:
3471:
3467:
3462:
3457:
3453:
3448:
3443:
3439:
3434:
3429:
3425:
3420:
3414:
3409:
3404:
3400:
3395:
3389:
3384:
3379:
3375:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3312:
3307:
3302:
3298:
3293:
3288:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3243:
3238:
3233:
3228:
3224:
3219:
3214:
3210:
3205:
3200:
3196:
3192:
3185:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3080:
3075:
3069:
3064:
3059:
3054:
3049:
3045:
3040:
3035:
3031:
3025:
3022:
3021:
3014:
3013:
3006:
2999:
2991:
2982:
2981:
2979:
2978:
2977:
2976:
2971:
2959:
2952:
2946:
2943:
2942:
2940:
2939:
2937:Sulfinylamines
2934:
2929:
2924:
2919:
2917:Phosphoramides
2914:
2912:Isothiocyanate
2908:
2906:
2902:
2901:
2898:
2897:
2895:
2894:
2889:
2888:
2887:
2877:
2876:
2875:
2865:
2864:
2863:
2858:
2853:
2848:
2843:
2832:
2830:
2822:
2821:
2819:
2818:
2813:
2807:
2805:
2799:
2798:
2796:
2795:
2790:
2788:Selenenic acid
2785:
2783:Seleninic acid
2780:
2778:Selenonic acid
2775:
2769:
2767:
2761:
2760:
2758:
2757:
2752:
2746:
2744:
2738:
2737:
2735:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2658:
2657:
2647:
2641:
2639:
2633:
2632:
2630:
2629:
2624:
2619:
2614:
2613:
2612:
2602:
2597:
2592:
2587:
2586:
2585:
2575:
2574:
2573:
2571:Phosphodiester
2562:
2560:
2554:
2553:
2551:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2449:
2448:
2443:
2432:
2430:
2421:
2417:(one element,
2401:
2400:
2397:
2396:
2394:
2393:
2392:
2391:
2381:
2380:
2379:
2374:
2363:
2361:
2357:
2356:
2354:
2353:
2348:
2343:
2342:
2341:
2331:
2330:
2329:
2324:
2319:
2308:
2306:
2300:
2299:
2297:
2296:
2294:Methylenedioxy
2291:
2286:
2285:
2284:
2279:
2269:
2268:
2267:
2262:
2252:
2251:
2250:
2240:
2235:
2229:
2227:
2220:
2198:
2197:
2195:
2194:
2189:
2184:
2183:
2182:
2177:
2167:
2166:
2165:
2160:
2155:
2150:
2145:
2140:
2130:
2129:
2128:
2123:
2113:
2112:
2111:
2106:
2101:
2096:
2091:
2086:
2075:
2073:
2071:(only C and H)
2063:
2062:
2055:
2054:
2047:
2040:
2032:
2024:
2023:
1990:
1971:(2): 273–412.
1955:
1938:
1931:
1905:
1899:978-3527306732
1898:
1870:
1839:
1832:
1803:
1768:
1762:978-3527306732
1761:
1730:
1713:
1694:(3): 127–140.
1678:
1663:
1645:
1630:
1612:
1577:
1570:
1539:
1533:
1508:
1507:
1505:
1502:
1499:
1498:
1491:
1479:
1478:
1476:
1473:
1464:
1461:
1456:
1452:
1444:
1443:
1440:
1436:
1432:
1428:
1424:
1420:
1416:
1399:
1395:
1392:
1391:
1390:
1385:
1381:
1377:
1373:
1356:
1352:
1349:
1348:
1347:
1343:
1339:
1315:
1303:
1302:Esterification
1300:
1291:
1290:
1286:
1282:
1278:
1274:
1270:
1266:
1262:
1258:
1246:Main article:
1243:
1240:
1236:
1235:
1230:
1226:
1222:
1218:
1214:
1210:
1206:
1202:
1193:
1190:
1185:
1182:
1156:
1153:
1118:
1115:
1079:
1075:
1063:
1062:Acid catalysts
1060:
1031:
1028:
992:
989:
984:
981:
980:
979:
965:
958:
956:
942:
935:
933:
923:
916:
914:
905:
898:
896:
890:
883:
881:
867:
860:
858:
846:
831:
824:
817:
805:
798:
782:
758:
755:
745:
741:
737:
733:
728:carbyl sulfate
700:
697:
689:
688:
668:
660:
652:
642:
639:
634:
612:
611:
597:
589:
578:
570:
564:
559:
554:
538:
518:
505:
492:
484:
479:
471:
463:
454:
447:
442:
437:
394:
393:
373:
365:
357:
347:
344:
339:
331:
323:
297:sulfur dioxide
274:
273:
253:
240:
227:
219:
211:
203:
195:
182:
138:
135:
117:
112:sulfurous acid
101:
73:
70:group and the
57:
48:sulphonic acid
26:
9:
6:
4:
3:
2:
3923:
3912:
3909:
3907:
3904:
3903:
3901:
3886:
3877:
3875:
3866:
3864:
3852:
3850:
3838:
3836:
3824:
3822:
3813:
3811:
3798:
3796:
3780:
3778:
3762:
3760:
3744:
3742:
3733:
3731:
3715:
3713:
3701:
3699:
3687:
3685:
3673:
3671:
3668:
3666:
3663:
3661:
3648:
3646:
3634:
3632:
3620:
3618:
3606:
3604:
3595:
3593:
3581:
3579:
3570:
3568:
3555:
3553:
3537:
3535:
3519:
3517:
3505:
3503:
3491:
3489:
3477:
3475:
3463:
3461:
3449:
3447:
3435:
3433:
3421:
3419:
3410:
3408:
3396:
3394:
3385:
3383:
3367:
3365:
3357:
3355:
3347:
3345:
3342:
3340:
3337:
3335:
3327:
3325:
3322:
3320:
3308:
3306:
3294:
3292:
3284:
3282:
3274:
3272:
3264:
3262:
3254:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3220:
3218:
3206:
3204:
3177:
3175:
3172:
3170:
3167:
3165:
3157:
3155:
3147:
3145:
3137:
3135:
3132:
3130:
3127:
3125:
3117:
3115:
3107:
3105:
3097:
3095:
3092:
3090:
3087:
3085:
3076:
3074:
3065:
3063:
3060:
3058:
3055:
3053:
3041:
3039:
3027:
3026:
3023:
3019:
3012:
3007:
3005:
3000:
2998:
2993:
2992:
2989:
2975:
2972:
2970:
2967:
2966:
2965:
2964:
2960:
2958:
2957:
2953:
2948:
2947:
2944:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2909:
2907:
2903:
2893:
2890:
2886:
2883:
2882:
2881:
2878:
2874:
2871:
2870:
2869:
2866:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2838:
2837:
2834:
2833:
2831:
2829:
2828:
2823:
2817:
2816:Telluroketone
2814:
2812:
2809:
2808:
2806:
2804:
2800:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2770:
2768:
2766:
2762:
2756:
2753:
2751:
2748:
2747:
2745:
2743:
2739:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2702:Sulfonic acid
2700:
2698:
2695:
2693:
2692:Sulfinic acid
2690:
2688:
2687:Thiosulfonate
2685:
2683:
2680:
2678:
2677:Thiosulfinate
2675:
2673:
2672:Sulfenic acid
2670:
2668:
2665:
2663:
2660:
2656:
2653:
2652:
2651:
2648:
2646:
2643:
2642:
2640:
2638:
2634:
2628:
2627:Phosphaallene
2625:
2623:
2622:Phosphaalkyne
2620:
2618:
2617:Phosphaalkene
2615:
2611:
2608:
2607:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2584:
2581:
2580:
2579:
2576:
2572:
2569:
2568:
2567:
2564:
2563:
2561:
2559:
2555:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2447:
2444:
2442:
2439:
2438:
2437:
2434:
2433:
2431:
2429:
2425:
2422:
2402:
2390:
2387:
2386:
2385:
2382:
2378:
2375:
2373:
2370:
2369:
2368:
2365:
2364:
2362:
2358:
2352:
2349:
2347:
2344:
2340:
2337:
2336:
2335:
2332:
2328:
2325:
2323:
2320:
2318:
2315:
2314:
2313:
2310:
2309:
2307:
2305:
2301:
2295:
2292:
2290:
2289:Ethylenedioxy
2287:
2283:
2280:
2278:
2275:
2274:
2273:
2270:
2266:
2263:
2261:
2258:
2257:
2256:
2253:
2249:
2246:
2245:
2244:
2241:
2239:
2236:
2234:
2231:
2230:
2228:
2224:
2221:
2215:
2209:
2204:
2199:
2193:
2190:
2188:
2185:
2181:
2178:
2176:
2173:
2172:
2171:
2168:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2135:
2134:
2131:
2127:
2124:
2122:
2119:
2118:
2117:
2114:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2087:
2085:
2082:
2081:
2080:
2077:
2076:
2074:
2068:
2064:
2060:
2053:
2048:
2046:
2041:
2039:
2034:
2033:
2030:
2018:
2013:
2009:
2005:
2001:
1994:
1986:
1982:
1978:
1974:
1970:
1966:
1959:
1952:
1948:
1942:
1934:
1928:
1924:
1920:
1916:
1909:
1901:
1895:
1891:
1887:
1883:
1882:
1874:
1866:
1862:
1858:
1854:
1850:
1843:
1835:
1829:
1825:
1821:
1817:
1810:
1808:
1799:
1795:
1791:
1787:
1783:
1779:
1772:
1764:
1758:
1754:
1750:
1746:
1745:
1737:
1735:
1727:
1723:
1717:
1709:
1705:
1701:
1697:
1693:
1689:
1682:
1674:
1670:
1666:
1660:
1656:
1649:
1641:
1637:
1633:
1627:
1623:
1616:
1608:
1604:
1600:
1596:
1592:
1588:
1581:
1573:
1571:3-527-30673-0
1567:
1563:
1559:
1555:
1554:
1546:
1544:
1536:
1534:0-471-60180-2
1530:
1526:
1522:
1516:
1514:
1509:
1484:
1480:
1472:
1470:
1460:
1450:
1427:Na + NaOH → C
1414:
1413:
1412:
1410:
1406:
1370:
1369:
1368:
1366:
1362:
1337:
1336:
1335:
1333:
1329:
1325:
1321:
1313:
1309:
1299:
1297:
1255:
1254:
1253:
1249:
1239:
1199:
1198:
1197:
1189:
1177:
1173:
1171:
1167:
1162:
1149:
1144:
1140:
1138:
1131:
1127:
1123:
1114:
1112:
1108:
1104:
1100:
1096:
1092:
1088:
1086:
1073:
1069:
1059:
1057:
1053:
1049:
1045:
1044:carbohydrates
1041:
1037:
1036:anthraquinone
1027:
1025:
1021:
1017:
1013:
1009:
1005:
1001:
997:
988:
976:
972:
968:
962:
957:
953:
949:
945:
939:
934:
930:
926:
920:
915:
911:
909:
902:
897:
893:
887:
882:
878:
874:
870:
864:
859:
856:
855:
854:
852:
851:sulfuric acid
844:
839:
835:
830:
823:
815:
811:
804:
797:
793:
789:
785:
781:
775:
771:
769:
764:
754:
752:
729:
725:
721:
719:
718:Reed reaction
714:
710:
706:
696:
694:
666:
650:
640:
637:
632:
621:
620:
619:
617:
595:
587:
576:
562:
557:
552:
539:
516:
503:
490:
477:
469:
461:
452:
445:
440:
435:
422:
421:
420:
418:
417:alkyl halides
414:
410:
405:
403:
399:
371:
355:
345:
342:
337:
329:
321:
310:
309:
308:
306:
302:
298:
294:
293:sulfoxidation
289:
287:
283:
279:
251:
238:
225:
209:
201:
193:
180:
167:
166:
165:
163:
159:
155:
147:
143:
134:
132:
128:
124:
113:
109:
97:
93:
89:
88:sulfuric acid
85:
81:
69:
65:
53:
49:
45:
44:sulfonic acid
41:
32:
19:
3880:H[Co(CO)
2961:
2954:
2868:Vinyl halide
2825:
2755:Borinic acid
2750:Boronic acid
2727:Thioxanthate
2701:
2067:Hydrocarbons
2007:
2003:
1993:
1968:
1964:
1958:
1941:
1914:
1908:
1879:
1873:
1856:
1852:
1848:
1842:
1815:
1781:
1777:
1771:
1742:
1716:
1691:
1687:
1681:
1654:
1648:
1621:
1615:
1590:
1586:
1580:
1551:
1524:
1521:March, Jerry
1483:
1466:
1463:o-Lithiation
1445:
1397:
1354:
1351:Halogenation
1305:
1292:
1251:
1237:
1195:
1187:
1158:
1135:
1084:
1065:
1033:
994:
986:
983:Applications
907:
840:
836:
828:
821:
802:
795:
788:benzoic acid
779:
767:
760:
722:
702:
690:
613:
406:
395:
290:
278:electrophile
275:
151:
83:
47:
43:
37:
2932:Thiocyanate
2927:Sulfonamide
2892:Perchlorate
2880:Acyl halide
2841:Fluoroethyl
2722:Thionoester
2610:Phosphonium
2595:Phosphinate
2590:Phosphonous
2578:Phosphonate
2277:Hydroperoxy
2099:Cyclopropyl
1332:alcoholysis
1137:Sulfa drugs
1126:Acamprosate
1099:polystyrene
1008:fatty acids
1000:surfactants
975:natural gas
973:, found in
792:acetic acid
305:surfactants
154:sulfonation
137:Preparation
92:substituent
84:sulfo group
3900:Categories
2836:Haloalkane
2707:Thioketone
2662:Persulfide
2558:Phosphorus
2523:Isocyanate
2513:Isonitrile
2414:or oxygen
2412:hydrogen,
2408:not being
2389:Orthoester
2282:Dioxiranes
2260:Enol ether
2148:1-Propenyl
1851:-Cresol".
1504:References
1111:fuel cells
996:Detergents
967:Coenzyme-M
948:surfactant
929:fuel cells
763:carboxylic
757:Properties
131:sulfonates
3562:[PtCl
2969:inorganic
2803:Tellurium
2717:Thioester
2682:Sulfoxide
2667:Disulfide
2655:Sulfonium
2605:Phosphine
2583:Phosphite
2566:Phosphate
2498:Carbamate
2473:Hydrazone
2406:element,
2404:Only one
2377:Anhydride
2116:Methylene
1985:0009-2665
1778:Chem. Rev
1708:1463-9262
1673:867050415
1640:708034394
1607:0001-4842
1346:OR′ + HCl
1273:O → R−C
1184:Reactions
1168:, useful
1068:catalysts
873:bile acid
834:= −5.9).
820:, whose p
814:sulfonate
659:⟶
596:−
569:⟶
558:−
483:⟶
441:−
413:alkylated
409:bisulfite
364:⟶
218:⟶
116:S(=O)(OH)
3655:[SiF
3079:H[BF
2950:See also
2885:Chloride
2811:Tellurol
2765:Selenium
2732:Xanthate
2446:Ammonium
2428:Nitrogen
2410:carbon,
2367:Carboxyl
2334:Aldehyde
2322:Acryloyl
2304:carbonyl
2208:hydrogen
2163:Cumulene
1798:17973436
1523:(1992),
1388:F + HF
1380:H → SOF
1170:ionomers
1052:sulfonyl
1040:proteins
1024:concrete
950:used in
877:tautomer
751:ethylene
280:and the
108:tautomer
80:sulfonyl
78:group a
2974:organic
2773:Selenol
2697:Sulfone
2650:Sulfide
2548:NONOate
2543:Nitroso
2533:Nitrite
2528:Nitrate
2518:Cyanate
2508:Nitrile
2493:Amidine
2488:Imidate
2458:Nitrene
2453:Hydrazo
2441:Enamine
2372:Acetoxy
2360:carboxy
2327:Benzoyl
2265:Epoxide
2248:Methoxy
2238:Alcohol
2192:Carbene
2126:Methine
1449:benzyne
1435:OH + Na
1221:OH + Na
1159:In the
1082:OH and
971:methane
869:Taurine
693:taurine
56:R−S(=O)
2873:Iodide
2793:Selone
2637:Sulfur
2346:Ketone
2339:Ketene
2317:Acetyl
2272:Peroxy
2243:Alkoxy
2233:Acetal
2214:oxygen
2203:carbon
2187:Alkyne
2180:Benzyl
2175:Phenyl
2158:Allene
2153:Crotyl
2133:Alkene
2121:Bridge
2109:Pentyl
2094:Propyl
2084:Methyl
1983:
1929:
1896:
1859:: 37.
1830:
1796:
1759:
1706:
1671:
1661:
1638:
1628:
1605:
1568:
1531:
1490:HS(=O)
1405:phenol
1308:esters
1107:Nafion
1016:lignin
925:Nafion
616:thiols
301:oxygen
127:esters
100:HS(=O)
94:. The
3330:NaHCO
2905:Other
2742:Boron
2712:Thial
2645:Thiol
2538:Nitro
2503:Imide
2483:Amide
2468:Oxime
2463:Imine
2436:Amine
2384:Ester
2351:Ynone
2255:Ether
2226:R-O-R
2201:Only
2143:Allyl
2138:Vinyl
2104:Butyl
2089:Ethyl
2079:Alkyl
1475:Notes
1384:+ RSO
1376:+ RSO
1269:H + H
1117:Drugs
1095:Dowex
1004:soaps
776:have
282:arene
123:Salts
72:S(=O)
64:alkyl
3670:HNCS
3665:HSCN
3339:HNCO
3287:HMnO
3174:HCNO
3160:HClO
3150:HClO
3140:HClO
3134:HClO
3120:HBrO
3110:HBrO
3100:HBrO
3094:HBrO
3057:HArF
2827:Halo
2312:Acyl
2212:and
2170:Aryl
1981:ISSN
1927:ISBN
1894:ISBN
1828:ISBN
1794:PMID
1757:ISBN
1704:ISSN
1669:OCLC
1659:ISBN
1636:OCLC
1626:ISBN
1603:ISSN
1566:ISBN
1529:ISBN
1074:, CH
1048:dyes
1042:and
1030:Dyes
998:and
892:PFOS
871:, a
810:salt
790:and
772:and
299:and
106:, a
104:(OH)
76:(OH)
68:aryl
46:(or
3859:TiO
3845:TeO
3831:TeO
3641:SiO
3627:SeO
3613:SeO
3403:NSO
3388:HNO
3360:HNO
3350:HNO
3344:HNO
3324:HNC
3315:MoO
3301:MnO
3277:HIO
3267:HIO
3257:HIO
3251:HIO
3241:HFO
3184:CrO
3169:HCN
3129:HCl
3089:HBr
3068:HSO
3062:HAt
3048:AsO
3034:AsO
2478:Azo
2012:doi
1973:doi
1947:doi
1919:doi
1886:doi
1861:doi
1820:doi
1786:doi
1782:107
1749:doi
1722:doi
1696:doi
1595:doi
1558:doi
1338:RSO
1326:in
1281:+ H
1257:R−C
1229:+ H
1105:).
818:(g)
740:(SO
730:, (
663:RSO
630:RSH
573:RSO
566:RBr
549:HSO
487:RCH
449:RCH
432:HSO
415:by
400:to
368:RSO
288:.
125:or
110:of
66:or
60:−OH
38:In
3902::
3873:Po
3820:Te
3805:SO
3801:CF
3708:SO
3694:SO
3680:SO
3602:Se
3550:10
3512:PO
3498:PO
3484:PO
3246:HI
3236:HF
3227:CS
3213:CO
3195:Cr
2210:,
2205:,
2008:39
2006:.
2002:.
1979:.
1969:49
1967:.
1925:.
1892:.
1855:.
1826:.
1806:^
1792:.
1780:.
1755:.
1733:^
1702:.
1690:.
1667:.
1634:.
1601:.
1591:21
1589:.
1564:.
1542:^
1512:^
1439:SO
1423:SO
1372:SF
1367::
1285:SO
1265:SO
1225:SO
1209:SO
1113:.
1078:SO
1026:.
879:).
853:.
753:.
720:.
695:.
618::
592:Br
513:SO
500:CH
458:CH
419::
404:.
326:SO
319:RH
307:.
248:SO
222:RC
206:SO
177:RC
164::
133:.
121:.
114:,
42:,
3884:]
3882:4
3871:2
3869:H
3861:4
3857:4
3855:H
3847:6
3843:6
3841:H
3833:3
3829:2
3827:H
3818:2
3816:H
3809:H
3807:3
3803:3
3793:8
3791:O
3789:2
3787:S
3785:2
3783:H
3775:7
3773:O
3771:2
3769:S
3767:2
3765:H
3757:6
3755:O
3753:2
3751:S
3749:2
3747:H
3740:O
3738:3
3736:H
3728:3
3726:O
3724:2
3722:S
3720:2
3718:H
3710:5
3706:2
3704:H
3696:4
3692:2
3690:H
3682:3
3678:2
3676:H
3659:]
3657:6
3653:2
3651:H
3643:4
3639:4
3637:H
3629:4
3625:2
3623:H
3615:3
3611:2
3609:H
3600:2
3598:H
3590:2
3588:S
3586:2
3584:H
3577:S
3575:2
3573:H
3566:]
3564:6
3560:2
3558:H
3548:O
3546:3
3544:P
3542:5
3540:H
3532:7
3530:O
3528:2
3526:P
3524:4
3522:H
3514:4
3510:3
3508:H
3500:3
3496:3
3494:H
3486:2
3482:3
3480:H
3472:5
3470:O
3468:2
3466:H
3458:4
3456:O
3454:2
3452:H
3444:3
3442:O
3440:2
3438:H
3430:2
3428:O
3426:2
3424:H
3417:O
3415:2
3413:H
3405:3
3401:3
3399:H
3392:S
3390:5
3380:2
3378:O
3376:2
3374:N
3372:2
3370:H
3362:3
3352:2
3332:3
3317:4
3313:2
3311:H
3303:4
3299:2
3297:H
3289:4
3279:4
3269:3
3259:2
3229:3
3225:2
3223:H
3215:3
3211:2
3209:H
3201:7
3199:O
3197:2
3193:2
3191:H
3189:/
3186:4
3182:2
3180:H
3162:4
3152:3
3142:2
3122:4
3112:3
3102:2
3083:]
3081:4
3072:F
3070:3
3050:4
3046:3
3044:H
3036:3
3032:3
3030:H
3010:e
3003:t
2996:v
2051:e
2044:t
2037:v
2020:.
2014::
1987:.
1975::
1953:.
1949::
1935:.
1921::
1902:.
1888::
1867:.
1863::
1857:3
1849:p
1836:.
1822::
1800:.
1788::
1765:.
1751::
1728:.
1724::
1710:.
1698::
1692:1
1675:.
1642:.
1609:.
1597::
1574:.
1560::
1496:.
1492:2
1457:2
1453:N
1447:(
1441:3
1437:2
1433:5
1431:H
1429:6
1425:3
1421:5
1419:H
1417:6
1415:C
1400:3
1386:2
1382:2
1378:3
1374:4
1357:2
1344:2
1340:2
1316:2
1287:4
1283:2
1279:5
1277:H
1275:6
1271:2
1267:3
1263:4
1261:H
1259:6
1233:O
1231:2
1227:3
1223:2
1219:5
1217:H
1215:6
1211:3
1207:5
1205:H
1203:6
1201:C
1132:.
1085:p
1080:2
1076:3
977:.
954:.
931:.
908:p
847:2
832:a
829:K
825:a
822:K
806:a
803:K
799:a
796:K
783:a
780:K
778:p
768:p
746:2
744:)
742:3
738:4
736:H
734:2
732:C
675:H
667:3
651:2
647:O
641:2
638:3
633:+
588:+
585:H
577:3
563:+
553:3
525:H
517:3
504:2
491:2
478:+
474:H
470:+
462:2
453:=
446:+
436:3
380:H
372:3
356:2
352:O
346:2
343:1
338:+
330:2
322:+
260:H
252:3
239:4
235:H
226:6
210:3
202:+
194:5
190:H
181:6
118:2
102:2
74:2
58:2
20:)
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