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Sulfenic acid

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SOH, are highly reactive and cannot be isolated in solution. In the gas phase the lifetime of methanesulfenic acid is about one minute. The gas phase structure of methanesulfenic acid was found by microwave spectroscopy
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were used to identify 2-propenesulfenic formed when garlic is cut or crushed and to demonstrate that this sulfenic acid has a lifetime of less than one second. The pharmacological activity of certain drugs, such as
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Goto K, Holler M, Okazaki R (1997). "Synthesis, Structure, and Reactions of a Sulfenic Acid Bearing a Novel Bowl-Type Substituent: The First Synthesis of a Stable Sulfenic Acid by Direct Oxidation of a Thiol".
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Dioctadecyl 3,3'-thiodipropanoate: Oxidation to the sulfoxide and subsequent Ei elimination generates a sulfenic acid. This material is used as a polymer stabilizer where it protects against long term heat
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that detoxify peroxides. They function by the conversion of a cysteine residue to a sulfenic acid. The sulfenic acid then converts to a disulfide by reaction with another residue of cysteine.
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Ishii A, Komiya K, Nakayama J (1996). "Synthesis of a Stable Sulfenic Acid by Oxidation of a Sterically Hindered Thiol (Thiophenetriptycene-8-thiol)1 and Its Characterization".
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Harrop, Todd C.; Mascharak, Pradip K. (2004). "Fe(III) and Co(III) Centers with Carboxamido Nitrogen and Modified Sulfur Coordination: Lessons Learned from Nitrile Hydratase".
112:, the structure of such stabilized sulfenic acids were shown to be R–S–O–H. The stable, sterically hindered sulfenic acid 1-triptycenesulfenic acid has been found to have a 1045:
Armstrong, C.; Plant, M.A.; Scott, G. (February 1975). "Mechanisms of antioxidant action: the nature of the redox behaviour of thiodipropionate esters in polypropylene".
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Sulfenic acid forms part of the series of chemical reactions that occur when cutting onions. The lachrymal glands are irritated by the end product of the reactions,
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Braverman, S., "Rearrangements involving sulfenic acids and their derivatives," in Sulfenic Acids and Derivatives, 1990, John Wiley & Sons.
1187: 196:. 1-Propenesulfenic acid, formed when onions are cut, is rapidly rearranged by a second enzyme, the lachrymatory factor synthase, giving 971:
Michael Carrasco, Robert J. Jones, Scott Kamel, H. Rapoport, Thien Truong (1992). "N-(Benzyloxycarbonyl)-L-Vinylglycine Methyl Ester".
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have the formula RSOR′. They arise by the reaction of sulfenyl chlorides on alcohols. Sulfenate esters are intermediates in the
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Block E, Dane AJ, Thomas S, Cody RB (2010). "Applications of Direct Analysis in Real Time–Mass Spectrometry (DART-MS) in
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where they protects against long term heat ageing, structures based on thiodipropionate esters are popular.
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Vaidya V, Ingold KU, Pratt DA (2009). "Garlic: Source of the Ultimate Antioxidants – Sulfenic Acids".
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Rhee, Sue Goo; Kil, In Sup (2017). "Multiple Functions and Regulation of Mammalian Peroxiredoxins".
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In contrast to sulfinic and sulfonic acids, simple sulfenic acids, such as methanesulfenic acid, CH
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McGrath AJ, Garrett GE, Valgimigli L, Pratt DA (2010). "The redox chemistry of sulfenic acids".
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in organic nomenclature denotes the RS group (R ≠ H). One example is methane
2059: 2029: 1787: 1409: 1089: 1058: 1025: 908: 845: 796: 757: 714: 677: 652: 617: 479: 444: 1116: 51:. It is the first member of the family of organosulfur oxoacids, which also include 1764: 1258: 1196: 1149: 1120: 1111: 1081: 1054: 1017: 980: 955: 898: 890: 835: 827: 788: 749: 740:-Oxide and Other Reactive Sulfur Compounds from Crushed Garlic and Other Alliums". 706: 644: 609: 582: 555: 527: 1983: 1742: 1737: 1720: 1703: 1504: 1253: 894: 671: 212: 2054: 2049: 1925: 1920: 1915: 1708: 1675: 1459: 1441: 1431: 163: 19: 959: 792: 459: 2128: 2074: 2022: 1953: 1839: 1829: 1824: 1814: 1759: 1754: 1670: 1665: 1655: 1509: 1464: 1426: 1414: 1385: 1263: 1154: 1137: 1115:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) " 984: 736:
Chemistry. 2-Propenesulfenic and 2-Propenesulfinic Acids, Diallyl Trisulfane
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to the corresponding protein sulfenic acids is suggested to be important in
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of ≥14 and O–H BDE of ~88 kcal/mol for the (valence) isoelectronic
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is proposed to involve sulfenic acid intermediates. Oxidation of
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Reference Module in Materials Science and Materials Engineering
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group is proposed as the nucleophile that attacks the nitrile.
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Petrovic, Goran; Saicic, Radomir N.; Cekovic, Zivorad (2005).
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Sulfenic acids are produced by the enzymatic decomposition of
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Penn RE, Block E, Revelle LK (1978). "Methanesulfenic Acid".
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of allyl sulfoxides. Sulfenamides have the formula RSNR′
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Biochimica et Biophysica Acta (BBA) - General Subjects
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While sulfenic acids have the potential of exhibiting
1135: 300: 876: 1044: 731: 572: 673:Garlic and Other Alliums: The Lore and the Science 417: 262: 877:Gupta, Vinayak; Kate S. Carroll (February 2014). 696: 544: 428:Compounds which react in this manner are used as 182:and related compounds following tissue damage to 2126: 517: 774: 1181: 1012:Kröhnke, C. (2016). "Polymer Stabilization". 997:: CS1 maint: multiple names: authors list ( 862:: CS1 maint: multiple names: authors list ( 1005: 454: 153: 1188: 1174: 927:"Why does chopping an onion make you cry?" 742:Journal of Agricultural and Food Chemistry 470:, yet another derivative of sulfenic acid. 1153: 902: 839: 669: 950: 948: 602:Journal of the American Chemical Society 575:Journal of the American Chemical Society 548:Journal of the American Chemical Society 520:Journal of the American Chemical Society 458: 266: 18: 1011: 781:Archives of Biochemistry and Biophysics 699:Angewandte Chemie International Edition 634: 279:can undergo thermal elimination via an 16:Organosulfur compound of the form R–SOH 2127: 207:. 2-Propenesulfenic acid, formed from 1195: 1169: 945: 649:10.1146/annurev-biochem-060815-014431 628: 173: 13: 1112:Compendium of Chemical Terminology 1022:10.1016/B978-0-12-803581-8.01487-9 814:Kettenhofen, NJ, Wood, MJ (2010). 14: 2146: 158: 190:, and other plants of the genus 1129: 1100: 1065: 1038: 964: 919: 870: 807: 263:Organic and inorganic chemistry 775:Mansuy D, Dansette PM (2011). 768: 725: 690: 676:. Royal Society of Chemistry. 663: 593: 566: 538: 511: 363: 320: 314: 1: 1074:Accounts of Chemical Research 637:Annual Review of Biochemistry 504: 78: 1059:10.1016/0014-3057(75)90141-X 895:10.1016/j.bbagen.2013.05.040 166:are ubiquitous and abundant 7: 10: 2151: 495:Mislow-Evans rearrangement 2083: 2042: 1962: 1939: 1901: 1878: 1773: 1694: 1564: 1541: 1497: 1440: 1363: 1338: 1203: 960:10.1002/9780470772287.ch8 933:. The Library of Congress 793:10.1016/j.abb.2010.09.015 464:Cyclohexylthiophthalimide 47:with the general formula 1155:10.15227/orgsyn.081.0244 1047:European Polymer Journal 985:10.15227/orgsyn.070.0029 455:Other sulfenyl compounds 257:syn-Propanethial-S-oxide 154:Formation and occurrence 124:bond-dissociation energy 2094:chemical classification 1125:10.1351/goldbook.S06098 90:rotational spectroscopy 2135:Organosulfur compounds 711:10.1002/anie.200804560 471: 419: 273: 28: 2101:chemical nomenclature 462: 420: 270: 110:X-ray crystallography 108:. Through the use of 73:hydrogen thioperoxide 41:organosulfur compound 22: 298: 291:and sulfenic acids: 1557:not C, H or O) 608:(47): 16759–16761. 581:(50): 12836–12837. 532:10.1021/ja00479a068 466:is an example of a 430:polymer stabilizers 392: 349: 336: 250:signal transduction 122:of 12.5 and an O–H 100:, RS(O)SR, such as 1999:Hypervalent iodine 931:Everyday Mysteries 820:Chem. Res. Toxicol 670:Block, E. (2010). 472: 445:nitrile hydratases 415: 380: 337: 324: 274: 29: 2122: 2121: 2060:Sulfenyl chloride 2038: 2037: 1537: 1536: 1356:(only C, H and O) 1197:Functional groups 1142:Organic Syntheses 1086:10.1021/ar0301532 1031:978-0-12-803581-8 973:Organic Syntheses 832:10.1021/tx100237w 826:(11): 1633–1646. 754:10.1021/jf1000106 683:978-0-85404-190-9 614:10.1021/ja1083046 587:10.1021/ja962995k 560:10.1021/ja962994s 526:(11): 3622–3624. 480:sulfenyl chloride 439:are found at the 409: 400: 383: 376: 368: 358: 340: 327: 319: 312: 304: 259:, causing tears. 174:Garlic and onions 2142: 2089: 1994:Trifluoromethoxy 1562: 1561: 1558: 1361: 1360: 1357: 1210: 1190: 1183: 1176: 1167: 1166: 1160: 1159: 1157: 1133: 1127: 1104: 1098: 1097: 1069: 1063: 1062: 1042: 1036: 1035: 1009: 1003: 1002: 996: 988: 968: 962: 952: 943: 942: 940: 938: 923: 917: 916: 906: 874: 868: 867: 861: 853: 843: 811: 805: 804: 772: 766: 765: 748:(8): 4617–4625. 729: 723: 722: 694: 688: 687: 667: 661: 660: 632: 626: 625: 597: 591: 590: 570: 564: 563: 554:(6): 1460–1461. 542: 536: 535: 515: 491:Sulfenate esters 450: 435:Sulfenate-based 424: 422: 421: 416: 414: 413: 407: 405: 398: 397: 391: 388: 381: 374: 373: 366: 362: 356: 354: 348: 345: 338: 335: 332: 325: 323: 317: 310: 309: 302: 70: 58: 50: 2150: 2149: 2145: 2144: 2143: 2141: 2140: 2139: 2125: 2124: 2123: 2118: 2087: 2079: 2034: 1989:Trichloromethyl 1984:Trifluoromethyl 1958: 1935: 1897: 1874: 1769: 1738:Phosphine oxide 1690: 1556: 1554: 1553: 1551: 1549: 1547: 1545: 1543: 1533: 1493: 1436: 1355: 1354: 1349: 1344: 1334: 1208: 1207: 1199: 1194: 1164: 1163: 1134: 1130: 1117:sulfenyl groups 1105: 1101: 1070: 1066: 1043: 1039: 1032: 1010: 1006: 990: 989: 969: 965: 953: 946: 936: 934: 925: 924: 920: 875: 871: 855: 854: 812: 808: 773: 769: 730: 726: 695: 691: 684: 668: 664: 633: 629: 598: 594: 571: 567: 543: 539: 516: 512: 507: 500: 489: 485: 457: 448: 406: 401: 393: 389: 384: 369: 355: 350: 346: 341: 333: 328: 313: 305: 301: 299: 296: 295: 287:to yield vinyl 284: 265: 213:DART ion source 176: 161: 156: 132: 120: 95: 86: 81: 68: 64: 56: 48: 17: 12: 11: 5: 2148: 2138: 2137: 2120: 2119: 2117: 2116: 2115: 2114: 2109: 2097: 2090: 2084: 2081: 2080: 2078: 2077: 2075:Sulfinylamines 2072: 2067: 2062: 2057: 2055:Phosphoramides 2052: 2050:Isothiocyanate 2046: 2044: 2040: 2039: 2036: 2035: 2033: 2032: 2027: 2026: 2025: 2015: 2014: 2013: 2003: 2002: 2001: 1996: 1991: 1986: 1981: 1970: 1968: 1960: 1959: 1957: 1956: 1951: 1945: 1943: 1937: 1936: 1934: 1933: 1928: 1926:Selenenic acid 1923: 1921:Seleninic acid 1918: 1916:Selenonic acid 1913: 1907: 1905: 1899: 1898: 1896: 1895: 1890: 1884: 1882: 1876: 1875: 1873: 1872: 1867: 1862: 1857: 1852: 1847: 1842: 1837: 1832: 1827: 1822: 1817: 1812: 1807: 1802: 1797: 1796: 1795: 1785: 1779: 1777: 1771: 1770: 1768: 1767: 1762: 1757: 1752: 1751: 1750: 1740: 1735: 1730: 1725: 1724: 1723: 1713: 1712: 1711: 1709:Phosphodiester 1700: 1698: 1692: 1691: 1689: 1688: 1683: 1678: 1673: 1668: 1663: 1658: 1653: 1648: 1643: 1638: 1633: 1628: 1623: 1618: 1613: 1608: 1603: 1598: 1593: 1588: 1587: 1586: 1581: 1570: 1568: 1559: 1555:(one element, 1539: 1538: 1535: 1534: 1532: 1531: 1530: 1529: 1519: 1518: 1517: 1512: 1501: 1499: 1495: 1494: 1492: 1491: 1486: 1481: 1480: 1479: 1469: 1468: 1467: 1462: 1457: 1446: 1444: 1438: 1437: 1435: 1434: 1432:Methylenedioxy 1429: 1424: 1423: 1422: 1417: 1407: 1406: 1405: 1400: 1390: 1389: 1388: 1378: 1373: 1367: 1365: 1358: 1336: 1335: 1333: 1332: 1327: 1322: 1321: 1320: 1315: 1305: 1304: 1303: 1298: 1293: 1288: 1283: 1278: 1268: 1267: 1266: 1261: 1251: 1250: 1249: 1244: 1239: 1234: 1229: 1224: 1213: 1211: 1209:(only C and H) 1201: 1200: 1193: 1192: 1185: 1178: 1170: 1162: 1161: 1128: 1099: 1080:(4): 253–260. 1064: 1053:(2): 161–167. 1037: 1030: 1004: 963: 944: 918: 889:(2): 847–875. 869: 806: 787:(1): 174–185. 767: 724: 689: 682: 662: 627: 592: 565: 537: 509: 508: 506: 503: 498: 483: 456: 453: 426: 425: 412: 404: 396: 387: 379: 372: 365: 361: 353: 344: 331: 322: 316: 308: 282: 264: 261: 201:-propanethial- 175: 172: 164:Peroxiredoxins 160: 159:Peroxiredoxins 157: 155: 152: 135:hydroperoxides 130: 118: 98:thiosulfinates 93: 84: 80: 77: 66: 61:sulfonic acids 53:sulfinic acids 15: 9: 6: 4: 3: 2: 2147: 2136: 2133: 2132: 2130: 2113: 2110: 2108: 2105: 2104: 2103: 2102: 2098: 2096: 2095: 2091: 2086: 2085: 2082: 2076: 2073: 2071: 2068: 2066: 2063: 2061: 2058: 2056: 2053: 2051: 2048: 2047: 2045: 2041: 2031: 2028: 2024: 2021: 2020: 2019: 2016: 2012: 2009: 2008: 2007: 2004: 2000: 1997: 1995: 1992: 1990: 1987: 1985: 1982: 1980: 1977: 1976: 1975: 1972: 1971: 1969: 1967: 1966: 1961: 1955: 1954:Telluroketone 1952: 1950: 1947: 1946: 1944: 1942: 1938: 1932: 1929: 1927: 1924: 1922: 1919: 1917: 1914: 1912: 1909: 1908: 1906: 1904: 1900: 1894: 1891: 1889: 1886: 1885: 1883: 1881: 1877: 1871: 1868: 1866: 1863: 1861: 1858: 1856: 1853: 1851: 1848: 1846: 1843: 1841: 1840:Sulfonic acid 1838: 1836: 1833: 1831: 1830:Sulfinic acid 1828: 1826: 1825:Thiosulfonate 1823: 1821: 1818: 1816: 1815:Thiosulfinate 1813: 1811: 1810:Sulfenic acid 1808: 1806: 1803: 1801: 1798: 1794: 1791: 1790: 1789: 1786: 1784: 1781: 1780: 1778: 1776: 1772: 1766: 1765:Phosphaallene 1763: 1761: 1760:Phosphaalkyne 1758: 1756: 1755:Phosphaalkene 1753: 1749: 1746: 1745: 1744: 1741: 1739: 1736: 1734: 1731: 1729: 1726: 1722: 1719: 1718: 1717: 1714: 1710: 1707: 1706: 1705: 1702: 1701: 1699: 1697: 1693: 1687: 1684: 1682: 1679: 1677: 1674: 1672: 1669: 1667: 1664: 1662: 1659: 1657: 1654: 1652: 1649: 1647: 1644: 1642: 1639: 1637: 1634: 1632: 1629: 1627: 1624: 1622: 1619: 1617: 1614: 1612: 1609: 1607: 1604: 1602: 1599: 1597: 1594: 1592: 1589: 1585: 1582: 1580: 1577: 1576: 1575: 1572: 1571: 1569: 1567: 1563: 1560: 1540: 1528: 1525: 1524: 1523: 1520: 1516: 1513: 1511: 1508: 1507: 1506: 1503: 1502: 1500: 1496: 1490: 1487: 1485: 1482: 1478: 1475: 1474: 1473: 1470: 1466: 1463: 1461: 1458: 1456: 1453: 1452: 1451: 1448: 1447: 1445: 1443: 1439: 1433: 1430: 1428: 1427:Ethylenedioxy 1425: 1421: 1418: 1416: 1413: 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705:(1): 157–60. 704: 700: 693: 685: 679: 675: 674: 666: 658: 654: 650: 646: 642: 638: 631: 623: 619: 615: 611: 607: 603: 596: 588: 584: 580: 576: 569: 561: 557: 553: 549: 541: 533: 529: 525: 521: 514: 510: 502: 496: 492: 487: 481: 477: 469: 465: 461: 452: 446: 442: 438: 433: 431: 410: 402: 394: 385: 377: 370: 359: 351: 342: 329: 306: 294: 293: 292: 290: 286: 278: 269: 260: 258: 253: 251: 247: 243: 239: 235: 231: 227: 223: 219: 214: 210: 206: 204: 200: 195: 194: 189: 185: 181: 171: 169: 165: 151: 149: 146: 143: 140: 136: 129: 125: 121: 117: 111: 107: 103: 99: 91: 76: 74: 62: 54: 46: 42: 38: 37:sulfenic acid 34: 26: 21: 2099: 2092: 2006:Vinyl halide 1963: 1893:Borinic acid 1888:Boronic acid 1865:Thioxanthate 1809: 1205:Hydrocarbons 1145: 1141: 1131: 1110: 1102: 1077: 1073: 1067: 1050: 1046: 1040: 1013: 1007: 993:cite journal 976: 972: 966: 935:. Retrieved 930: 921: 886: 882: 872: 858:cite journal 823: 819: 809: 784: 780: 770: 745: 741: 737: 733: 727: 702: 698: 692: 672: 665: 640: 636: 630: 605: 601: 595: 578: 574: 568: 551: 547: 540: 523: 519: 513: 490: 488: 475: 473: 434: 427: 275: 254: 240:residues in 222:esomeprazole 202: 198: 191: 177: 162: 127: 115: 82: 36: 30: 2070:Thiocyanate 2065:Sulfonamide 2030:Perchlorate 2018:Acyl halide 1979:Fluoroethyl 1860:Thionoester 1748:Phosphonium 1733:Phosphinate 1728:Phosphonous 1716:Phosphonate 1415:Hydroperoxy 1237:Cyclopropyl 643:: 749–775. 474:The prefix 468:sulfenamide 441:active site 230:clopidogrel 226:ticlopidine 25:tautomerism 1974:Haloalkane 1845:Thioketone 1800:Persulfide 1696:Phosphorus 1661:Isocyanate 1651:Isonitrile 1552:or oxygen 1550:hydrogen, 1546:not being 1527:Orthoester 1420:Dioxiranes 1398:Enol ether 1286:1-Propenyl 505:References 277:Sulfoxides 248:-mediated 218:omeprazole 92:) to be CH 79:Properties 2107:inorganic 1941:Tellurium 1855:Thioester 1820:Sulfoxide 1805:Disulfide 1793:Sulfonium 1743:Phosphine 1721:Phosphite 1704:Phosphate 1636:Carbamate 1611:Hydrazone 1544:element, 1542:Only one 1515:Anhydride 1254:Methylene 403:− 371:− 364:⟶ 352:− 307:− 285:mechanism 234:prasugrel 57:R−S(=O)OH 33:chemistry 2129:Category 2088:See also 2023:Chloride 1949:Tellurol 1903:Selenium 1870:Xanthate 1584:Ammonium 1566:Nitrogen 1548:carbon, 1505:Carboxyl 1472:Aldehyde 1460:Acryloyl 1442:carbonyl 1346:hydrogen 1301:Cumulene 1094:15096062 913:23748139 850:20845928 801:20869346 762:20225897 719:19040240 657:28226215 622:21049943 476:sulfenyl 411:′ 360:′ 238:cysteine 2112:organic 1911:Selenol 1835:Sulfone 1788:Sulfide 1686:NONOate 1681:Nitroso 1671:Nitrite 1666:Nitrate 1656:Cyanate 1646:Nitrile 1631:Amidine 1626:Imidate 1596:Nitrene 1591:Hydrazo 1579:Enamine 1510:Acetoxy 1498:carboxy 1465:Benzoyl 1403:Epoxide 1386:Methoxy 1376:Alcohol 1330:Carbene 1264:Methine 1148:: 244. 937:1 April 904:4184475 841:2990351 486:SCl. 447:. The 443:of the 437:ligands 289:alkenes 242:protein 209:allicin 168:enzymes 102:allicin 65:R−S(=O) 45:oxoacid 2011:Iodide 1931:Selone 1775:Sulfur 1484:Ketone 1477:Ketene 1455:Acetyl 1410:Peroxy 1381:Alkoxy 1371:Acetal 1352:oxygen 1341:carbon 1325:Alkyne 1318:Benzyl 1313:Phenyl 1296:Allene 1291:Crotyl 1271:Alkene 1259:Bridge 1247:Pentyl 1232:Propyl 1222:Methyl 1092:  1028:  979:: 29. 911:  901:  848:  838:  799:  760:  734:Allium 717:  680:  655:  620:  272:ageing 232:, and 205:-oxide 193:Allium 188:onions 184:garlic 180:alliin 106:garlic 59:) and 49:R−S−OH 39:is an 2043:Other 1880:Boron 1850:Thial 1783:Thiol 1676:Nitro 1641:Imide 1621:Amide 1606:Oxime 1601:Imine 1574:Amine 1522:Ester 1489:Ynone 1393:Ether 1364:R-O-R 1339:Only 1281:Allyl 1276:Vinyl 1242:Butyl 1227:Ethyl 1217:Alkyl 1107:IUPAC 246:redox 104:from 1965:Halo 1450:Acyl 1350:and 1308:Aryl 1090:PMID 1026:ISBN 999:link 939:2019 909:PMID 887:1840 864:link 846:PMID 797:PMID 758:PMID 715:PMID 678:ISBN 653:PMID 618:PMID 482:, CH 43:and 35:, a 1616:Azo 1150:doi 1121:doi 1119:". 1082:doi 1055:doi 1018:doi 981:doi 956:doi 899:PMC 891:doi 836:PMC 828:doi 789:doi 785:507 750:doi 707:doi 645:doi 610:doi 606:132 583:doi 579:118 556:doi 552:119 528:doi 524:100 449:S=O 375:SOH 199:syn 31:In 2131:: 1348:, 1343:, 1146:81 1144:. 1140:. 1109:, 1088:. 1078:37 1076:. 1051:11 1049:. 1024:. 1016:. 995:}} 991:{{ 977:70 975:. 947:^ 929:. 907:. 897:. 885:. 881:. 860:}} 856:{{ 844:. 834:. 824:23 822:. 818:. 795:. 783:. 779:. 756:. 746:58 744:. 713:. 703:48 701:. 651:. 641:86 639:. 616:. 604:. 577:. 550:. 522:. 501:. 399:CH 382:CH 339:CH 326:CH 252:. 228:, 224:, 220:, 186:, 150:. 137:, 75:. 69:OH 1189:e 1182:t 1175:v 1158:. 1152:: 1123:: 1096:. 1084:: 1061:. 1057:: 1034:. 1020:: 1001:) 987:. 983:: 958:: 941:. 915:. 893:: 866:) 852:. 830:: 803:. 791:: 764:. 752:: 738:S 721:. 709:: 686:. 659:. 647:: 624:. 612:: 589:. 585:: 562:. 558:: 534:. 530:: 499:2 484:3 408:R 395:= 386:2 378:+ 367:R 357:R 343:2 330:2 321:) 318:O 315:( 311:S 303:R 283:i 281:E 203:S 148:H 145:O 142:O 139:R 131:a 128:K 119:a 116:K 114:p 94:3 88:( 85:3 67:2 63:( 55:(

Index


tautomerism
chemistry
organosulfur compound
oxoacid
sulfinic acids
sulfonic acids
hydrogen thioperoxide
rotational spectroscopy
thiosulfinates
allicin
garlic
X-ray crystallography
pKa
bond-dissociation energy
hydroperoxides
R
O
O
H
Peroxiredoxins
enzymes
alliin
garlic
onions
Allium
syn-propanethial-S-oxide
allicin
DART ion source
omeprazole

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