167:. The potential for methyl iodide to replace the ubiquitous dependence on methyl bromide as a soil fumigant has been considered, however limited information is available on environmental behavior of the former. Ioxynil (3,5-diiodo-4-hydroxybenzonitrile), which inhibits photosynthesis at photosystem II, is among the very few organoiodine herbicides. A member of the hydroxybenzonitrile herbicide class, ioxynil is an iodinated analog of the brominated herbicide,
320:
297:
248:
278:
263:
1736:
1587:
1655:
1492:
174:
Iodinated and brominated organic compounds are of concern as environmental contaminants owing to very limited information available on environment fate behavior. However, recent reports have shown promise in biological detoxification of these classes of contaminants. For example, Iodotyrosine
72:
Almost all organoiodine compounds feature iodide connected to one carbon center. These are usually classified as derivatives of I. Some organoiodine compounds feature iodine in higher oxidation states.
872:
Allard, A.S. and A. H. Neilson 2003 Degradation and transformation of organic bromine and iodine compounds: comparison with their chlorinated analogues. The
Handbook of Environmental Chemistry 3:1-74.
700:
179:
of iodine- or bromine-substituted organic substrates. Bromoxynil and ioxynil herbicides have been shown to undergo a variety of environmental transformations, including reductive dehalogenation by
392:
per year. The volatile iodomethane is broken up by oxidation reactions in the atmosphere and a global iodine cycle is established. More than 3000 organoiodine compounds have been identified.
408:
Organoiodine compounds are prepared by numerous routes, depending on the degree and regiochemistry of iodination sought as well as the nature of the precursors. The direct iodination with
202:
and contain about 50% by weight iodine. For most applications, the agent must be highly soluble in water and, of course, non-toxic and readily excreted. A representative reagent is
881:
McTamney, P.M. and S.E. Rokita 2010. A mammalian reductive deiodinase has broad power to dehalogenate chlorinated and brominated substrates. J Am Chem Soc. 131(40): 14212–14213.
890:
Cupples, A. M., R. A. Sanford, and G. K. Sims. 2005. Dehalogenation of
Bromoxynil (3,5-Dibromo-4-Hydroxybenzonitrile) and Ioxynil (3,5-Diiodino-4-Hydroxybenzonitrile) by
198:. This application exploits the X-ray absorbing ability of the heavy iodine nucleus. A variety of agents are available commercially, many are derivatives of 1,3,5-triiodo
840:
127:, because of the easy formation and cleavage of the C–I bond. Industrially significant organoiodine compounds, often used as disinfectants or pesticides, are
1170:
155:
I). Although methyl iodide is not an industrially important product, it is an important intermediate, being a transiently generated intermediate in the
111:
A noteworthy aspect of organoiodine compounds is their high density, which arises from the high atomic weight of iodine. For example, one millilitre of
277:
123:
Few organoiodine compounds are important industrially, at least in terms of large scale production. Iodide-containing intermediates are common in
100:, of 115, 83.7, 72.1, and 57.6 kcal/mol for X = fluoride, chloride, bromide, and iodide, respectively. Of the halides, iodide usually is the best
1163:
319:
891:
857:
711:
247:
903:
Ulrich Speck, Ute HĂĽbner-Steiner "Radiopaque Media" in
Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
776:
Alex G. Fallis, Pierre E. Tessier, "2-Iodoxybenzoic acid (IBX)1" Encyclopedia of
Reagents for Organic Synthesis, 2003 John Wiley
968:
N. Bell; L. Hsu; D. J. Jacob; M. G. Schultz; D. R. Blake; J. H. Butler; D. B. King; J. M. Lobert & E. Maier-Reimer (2002).
578:
1156:
156:
448:
The iodide anion is a good nucleophile and will displace chloride, tosylate, bromide and other leaving groups, as in the
296:
104:. Because of the weakness of the C–I bond, samples of organoiodine compounds are often yellow due to an impurity of I
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1660:
1603:
1497:
1418:
1413:
1270:
97:
1761:
1463:
1433:
1423:
1403:
1391:
1359:
1324:
1292:
1260:
1255:
1215:
1025:
V.M. Dembitsky; G.A. Tolstikov . (2003). "Naturally occurring organohalogen compounds - A comprehensive survey".
1230:
1194:
1148:
262:
1806:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1751:
1741:
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1547:
1532:
1512:
1507:
1458:
1386:
1369:
1319:
1314:
1309:
1304:
1280:
1240:
229:, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in
176:
1756:
1746:
1557:
1542:
1527:
1517:
1502:
1443:
1428:
1408:
1398:
1379:
1374:
1364:
1354:
1297:
1265:
742:
737:
1235:
1225:
1868:
1665:
1580:
1522:
1485:
1480:
1448:
1438:
1344:
1339:
1334:
1275:
1250:
802:
747:
1473:
1285:
1220:
1210:
60:
hormones are organoiodine compounds that are required for health and the reason for government-mandated
367:"). Marine natural products are rich sources of organoiodine compounds, like the recently discovered
92:
of halogens and the length of the carbon-halogen bond. For example, in the molecules represented by CH
1552:
1537:
1349:
1329:
981:
456:
449:
807:
1453:
721:
1007:
180:
933:
Gribble, G. W. (1996). "Naturally occurring organohalogen compounds - A comprehensive survey".
1125:
1042:
950:
853:
820:
343:
124:
81:
42:
970:"Methyl iodide: Atmospheric budget and use as a tracer of marine convection in global models"
1134:
1105:
1078:
1051:
997:
989:
942:
904:
845:
812:
777:
373:
368:
360:
325:
164:
136:
112:
1002:
349:
226:
195:
793:
Blanksby SJ, Ellison GB (April 2003). "Bond dissociation energies of organic molecules".
985:
569:
287:
187:
85:
969:
1862:
1825:
437:
253:
148:
101:
89:
53:
1011:
385:
61:
56:. They occur widely in organic chemistry, but are relatively rare in nature. The
757:
717:
464:
381:
348:
In terms of human health, the most important organoiodine compounds are the two
268:
215:
191:
160:
781:
533:
234:
168:
1138:
1109:
1082:
1055:
908:
849:
389:
352:
302:
238:
211:
57:
1069:
H. N. Rydon (1971). "Alkyl
Iodides: Neopentyl Iodide and Iodocyclohexane".
824:
954:
17:
993:
460:
283:
222:
203:
128:
946:
84:
of the halogen, decreasing in the order F > Cl > Br > I. This
310:
230:
199:
77:
816:
175:
deiodinase is a mammalian enzyme with the unusual function of aerobic
1180:
752:
50:
46:
27:
Organic compound containing at least one covalent carbon-iodine bond
724:
is a reagent that is sometimes used to deliver the equivalent of "
440:, an indicator of the unsaturation of fats and related samples.
388:, and the burning of biological material is estimated to be 214
207:
1152:
96:
X, where X is a halide, the carbon-X bonds have strengths, or
455:
Alcohols can be converted to the corresponding iodides using
919:"Key Lubrication Ingredient: Iodine Moves to Space Age",
716:
Benzene can be iodinated with a combination of iodide and
695:{\displaystyle {\ce {C6H5N2+ + KI -> C6H5I + K+ + N2}}}
384:
produced by the marine environment, microbial activity in
186:
Polyiodoorganic compounds are sometimes employed as X-ray
688:
656:
643:
606:
593:
1123:
F. B. Dains and R. Q. Brewster (1929). "Iodobenzene".
76:
The C–I bond is the weakest of the carbon–
1040:
King, C. S.; Hartman, W. W. (1933). "Methyl Iodide".
935:
Progress in the
Chemistry of Organic Natural Products
581:
1096:
Lucas, H. J.; Kennedy, E. R. (1939). "Iodobenzene".
1817:
694:
838:Phyllis A. Lyday. "Iodine and Iodine Compounds".
206:(Figure to right), which has water-solubilizing
80:bonds. These bond strengths correlate with the
33:is the study of the synthesis and properties of
841:Ullmann's Encyclopedia of Industrial Chemistry
1164:
396:Methods for preparation of the C–I bond
8:
286:, an organoiodine compound used as an X-ray
210:substituents. Typical applications include
1171:
1157:
1149:
1183:with other elements in the periodic table
1001:
806:
687:
682:
669:
655:
650:
642:
637:
618:
613:
605:
600:
592:
587:
582:
580:
415:is employed with unsaturated substrates:
221:Organoiodine lubricants can be used with
769:
568:Aromatic iodides may be prepared via a
436:This reaction is used to determine the
243:
1200:
68:Structure, bonding, general properties
536:of triphenylphosphite has been used.
256:, precursor to synthetic acetic acid.
171:(3,5-dibromo-4-hydroxybenzonitrile).
7:
1842:Academic research, no widespread use
894:. Appl. Env. Micro. 71(7):3741-3746.
572:by treatment with potassium iodide:
459:. Illustrative is the conversion of
892:Desulfitobacterium chlororespirans
712:Hypervalent organoiodine compounds
532:For bulky alcohol substrates, the
25:
1734:
1653:
1585:
1490:
1190:
318:
295:
276:
261:
246:
974:Journal of Geophysical Research
1003:11858/00-001M-0000-0012-0250-1
630:
1:
332:), another thyroid hormone.
1885:
782:10.1002/047084289X.rn00221
709:
341:
237:, and as a cutting oil in
98:bond dissociation energies
1731:
1650:
1202:
1198:
1188:
45:that contain one or more
1139:10.15227/orgsyn.009.0046
1110:10.15227/orgsyn.019.0055
1083:10.15227/orgsyn.051.0044
1056:10.15227/orgsyn.013.0060
1027:Nauka Press, Novosibirsk
909:10.1002/14356007.a22_593
850:10.1002/14356007.a14_381
743:Organochlorine compounds
738:Organofluorine compounds
177:reductive dehalogenation
844:. Weinheim: Wiley-VCH.
748:Organobromine compounds
119:Industrial applications
88:order also follows the
1837:Many uses in chemistry
1832:Core organic chemistry
696:
35:organoiodine compounds
31:Organoiodine chemistry
697:
342:Further information:
157:industrial production
994:10.1029/2001JD001151
923:, November 17, 1965.
579:
457:phosphorus triiodide
450:Finkelstein reaction
271:, a common food dye.
986:2002JGRD..107.4340B
947:10.1021/np50088a001
921:Schenectady Gazette
722:Iodine monochloride
690:
658:
645:
623:
608:
595:
692:
678:
646:
633:
609:
596:
583:
1856:
1855:
1812:
1811:
1126:Organic Syntheses
1098:Organic Syntheses
1071:Organic Syntheses
1043:Organic Syntheses
817:10.1021/ar020230d
681:
668:
661:
649:
636:
629:
612:
599:
586:
540:I + ROH → RI + CH
374:Plakortis simplex
369:plakohypaphorines
344:Iodine in biology
125:organic synthesis
82:electronegativity
43:organic compounds
16:(Redirected from
1876:
1848:
1843:
1838:
1833:
1738:
1737:
1657:
1656:
1589:
1588:
1494:
1493:
1191:
1173:
1166:
1159:
1150:
1143:
1141:
1120:
1114:
1113:
1093:
1087:
1086:
1066:
1060:
1058:
1037:
1031:
1030:
1022:
1016:
1015:
1005:
965:
959:
958:
930:
924:
917:
911:
901:
895:
888:
882:
879:
873:
870:
864:
863:
835:
829:
828:
810:
790:
784:
774:
727:
701:
699:
698:
693:
691:
689:
686:
679:
674:
673:
666:
659:
657:
654:
647:
644:
641:
634:
627:
622:
617:
610:
607:
604:
597:
594:
591:
584:
527:
526:
525:
517:
516:
506:
504:
503:
494:
490:
488:
487:
478:
432:
414:
371:from the sponge
361:triiodothyronine
350:thyroid hormones
326:Triiodothyronine
322:
299:
280:
265:
250:
227:stainless steels
165:acetic anhydride
137:methylene iodide
115:weighs 3.325 g.
113:methylene iodide
21:
1884:
1883:
1879:
1878:
1877:
1875:
1874:
1873:
1859:
1858:
1857:
1852:
1851:
1846:
1841:
1836:
1831:
1813:
1735:
1654:
1586:
1491:
1184:
1177:
1147:
1146:
1122:
1121:
1117:
1095:
1094:
1090:
1068:
1067:
1063:
1039:
1038:
1034:
1024:
1023:
1019:
967:
966:
962:
932:
931:
927:
918:
914:
902:
898:
889:
885:
880:
876:
871:
867:
860:
837:
836:
832:
808:10.1.1.616.3043
792:
791:
787:
775:
771:
766:
734:
725:
714:
708:
665:
577:
576:
563:
559:
555:
551:
547:
543:
524:
521:
520:
519:
515:
512:
511:
510:
508:
502:
499:
498:
497:
495:
492:
486:
483:
482:
481:
479:
476:
474:
446:
431:
427:
423:
419:
413:
409:
406:
404:
398:
366:
358:
346:
340:
338:Biological role
333:
331:
323:
314:
308:
300:
291:
281:
272:
266:
257:
251:
196:medical imaging
188:contrast agents
154:
146:
142:
134:
121:
107:
95:
70:
28:
23:
22:
15:
12:
11:
5:
1882:
1880:
1872:
1871:
1861:
1860:
1854:
1853:
1850:
1849:
1844:
1839:
1834:
1829:
1826:Chemical bonds
1822:
1821:
1819:
1815:
1814:
1810:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1759:
1754:
1749:
1744:
1739:
1732:
1729:
1728:
1723:
1718:
1713:
1708:
1703:
1698:
1693:
1688:
1683:
1678:
1673:
1668:
1663:
1658:
1651:
1648:
1647:
1643:
1642:
1639:
1636:
1633:
1630:
1627:
1624:
1621:
1618:
1615:
1612:
1609:
1606:
1601:
1598:
1595:
1590:
1583:
1578:
1574:
1573:
1570:
1565:
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1495:
1488:
1483:
1477:
1476:
1471:
1466:
1461:
1456:
1451:
1446:
1441:
1436:
1431:
1426:
1421:
1416:
1411:
1406:
1401:
1396:
1394:
1389:
1383:
1382:
1377:
1372:
1367:
1362:
1357:
1352:
1347:
1342:
1337:
1332:
1327:
1322:
1317:
1312:
1307:
1302:
1300:
1295:
1289:
1288:
1283:
1278:
1273:
1268:
1263:
1258:
1253:
1247:
1246:
1243:
1238:
1233:
1228:
1223:
1218:
1213:
1207:
1206:
1203:
1201:
1199:
1197:
1189:
1186:
1185:
1178:
1176:
1175:
1168:
1161:
1153:
1145:
1144:
1115:
1088:
1061:
1032:
1017:
960:
925:
912:
896:
883:
874:
865:
859:978-3527306732
858:
830:
795:Acc. Chem. Res
785:
768:
767:
765:
762:
761:
760:
755:
750:
745:
740:
733:
730:
707:
706:From I sources
704:
703:
702:
685:
677:
672:
664:
653:
640:
632:
626:
621:
616:
603:
590:
570:diazonium salt
566:
565:
561:
557:
553:
549:
545:
541:
530:
529:
522:
513:
500:
484:
472:
445:
444:From I sources
442:
434:
433:
429:
425:
421:
411:
405:
402:
399:
397:
394:
364:
356:
339:
336:
335:
334:
329:
324:
317:
315:
306:
301:
294:
292:
288:contrast agent
282:
275:
273:
267:
260:
258:
252:
245:
152:
144:
140:
132:
120:
117:
105:
93:
69:
66:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1881:
1870:
1869:Organoiodides
1867:
1866:
1864:
1845:
1840:
1835:
1830:
1827:
1824:
1823:
1820:
1816:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
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1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1748:
1745:
1743:
1740:
1733:
1730:
1727:
1724:
1722:
1719:
1717:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1672:
1669:
1667:
1664:
1662:
1659:
1652:
1649:
1645:
1644:
1640:
1637:
1634:
1631:
1628:
1625:
1622:
1619:
1616:
1613:
1610:
1607:
1605:
1602:
1599:
1596:
1594:
1591:
1584:
1582:
1579:
1576:
1575:
1571:
1569:
1566:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1489:
1487:
1484:
1482:
1479:
1478:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1440:
1437:
1435:
1432:
1430:
1427:
1425:
1422:
1420:
1417:
1415:
1412:
1410:
1407:
1405:
1402:
1400:
1397:
1395:
1393:
1390:
1388:
1385:
1384:
1381:
1378:
1376:
1373:
1371:
1368:
1366:
1363:
1361:
1358:
1356:
1353:
1351:
1348:
1346:
1343:
1341:
1338:
1336:
1333:
1331:
1328:
1326:
1323:
1321:
1318:
1316:
1313:
1311:
1308:
1306:
1303:
1301:
1299:
1296:
1294:
1291:
1290:
1287:
1284:
1282:
1279:
1277:
1274:
1272:
1269:
1267:
1264:
1262:
1259:
1257:
1254:
1252:
1249:
1248:
1244:
1242:
1239:
1237:
1234:
1232:
1229:
1227:
1224:
1222:
1219:
1217:
1214:
1212:
1209:
1208:
1204:
1196:
1193:
1192:
1187:
1182:
1179:Compounds of
1174:
1169:
1167:
1162:
1160:
1155:
1154:
1151:
1140:
1136:
1132:
1128:
1127:
1119:
1116:
1111:
1107:
1103:
1099:
1092:
1089:
1084:
1080:
1076:
1072:
1065:
1062:
1057:
1053:
1049:
1045:
1044:
1036:
1033:
1028:
1021:
1018:
1013:
1009:
1004:
999:
995:
991:
987:
983:
980:(D17): 4340.
979:
975:
971:
964:
961:
956:
952:
948:
944:
941:(10): 1–423.
940:
936:
929:
926:
922:
916:
913:
910:
906:
900:
897:
893:
887:
884:
878:
875:
869:
866:
861:
855:
851:
847:
843:
842:
834:
831:
826:
822:
818:
814:
809:
804:
801:(4): 255–63.
800:
796:
789:
786:
783:
779:
773:
770:
763:
759:
756:
754:
751:
749:
746:
744:
741:
739:
736:
735:
731:
729:
723:
719:
713:
705:
683:
675:
670:
662:
651:
638:
624:
619:
614:
601:
588:
575:
574:
573:
571:
539:
538:
537:
535:
470:
469:
468:
466:
462:
458:
453:
451:
443:
441:
439:
438:iodine number
418:
417:
416:
400:
395:
393:
391:
387:
383:
378:
376:
375:
370:
362:
354:
351:
345:
337:
327:
321:
316:
312:
304:
298:
293:
289:
285:
279:
274:
270:
264:
259:
255:
254:Methyl iodide
249:
244:
242:
240:
236:
232:
228:
224:
219:
217:
213:
209:
205:
201:
197:
193:
189:
184:
182:
178:
172:
170:
166:
162:
158:
150:
149:methyl iodide
138:
130:
126:
118:
116:
114:
109:
103:
102:leaving group
99:
91:
90:atomic radius
87:
83:
79:
74:
67:
65:
63:
59:
55:
52:
48:
44:
40:
39:organoiodides
36:
32:
19:
1847:Bond unknown
1468:
1130:
1124:
1118:
1101:
1097:
1091:
1074:
1070:
1064:
1047:
1041:
1035:
1026:
1020:
977:
973:
963:
938:
934:
928:
920:
915:
899:
886:
877:
868:
839:
833:
798:
794:
788:
772:
758:Periodinanes
715:
567:
531:
454:
447:
435:
407:
386:rice paddies
379:
372:
347:
220:
194:, a type of
185:
173:
122:
110:
75:
71:
38:
34:
30:
29:
718:nitric acid
465:iodomethane
382:iodomethane
380:The sum of
269:Erythrosine
216:angiography
192:fluoroscopy
161:acetic acid
764:References
710:See also:
534:methiodide
428:→ RHIC-CIH
390:kilotonnes
235:spacecraft
183:bacteria.
169:bromoxynil
62:iodization
18:Iodoalkane
1828:to carbon
803:CiteSeerX
631:⟶
353:thyroxine
303:Thyroxine
239:machining
212:urography
181:anaerobic
64:of salt.
58:thyroxine
1863:Category
1012:18327103
825:12693923
732:See also
461:methanol
284:Ioversol
231:turbines
223:titanium
204:Ioversol
129:iodoform
86:periodic
1646:
982:Bibcode
955:8795309
753:Iodanes
359:") and
311:hormone
200:benzene
147:), and
78:halogen
49:–
1818:Legend
1181:carbon
1133:: 46.
1104:: 55.
1077:: 44.
1050:: 60.
1010:
953:
856:
823:
805:
556:PO + C
493:
477:
420:RHC=CH
401:From I
51:iodine
47:carbon
1008:S2CID
309:), a
190:, in
54:bonds
37:, or
951:PMID
854:ISBN
821:PMID
233:and
214:and
208:diol
163:and
131:(CHI
1792:CEs
1787:CCf
1782:CBk
1777:CCm
1772:CAm
1767:CPu
1762:CNp
1752:CPa
1747:CTh
1726:CYb
1721:CTm
1716:CEr
1711:CHo
1706:CDy
1701:CTb
1696:CGd
1691:CEu
1686:CSm
1681:CPm
1676:CNd
1671:CPr
1666:CCe
1661:CLa
1641:Og
1638:Ts
1635:Lv
1632:Mc
1629:Fl
1626:Nh
1623:Cn
1620:Rg
1617:Ds
1614:Mt
1611:Hs
1608:Bh
1604:CSg
1600:Db
1597:Rf
1581:CRa
1577:Fr
1572:Rn
1568:CAt
1563:CPo
1558:CBi
1553:CPb
1548:CTl
1543:CHg
1538:CAu
1533:CPt
1528:CIr
1523:COs
1518:CRe
1508:CTa
1503:CHf
1498:CLu
1486:CBa
1481:CCs
1474:CXe
1464:CTe
1459:CSb
1454:CSn
1449:CIn
1444:CCd
1439:CAg
1434:CPd
1429:CRh
1424:CRu
1419:CTc
1414:CMo
1409:CNb
1404:CZr
1392:CSr
1387:CRb
1380:CKr
1375:CBr
1370:CSe
1365:CAs
1360:CGe
1355:CGa
1350:CZn
1345:CCu
1340:CNi
1335:CCo
1330:CFe
1325:CMn
1320:CCr
1310:CTi
1305:CSc
1298:CCa
1286:CAr
1281:CCl
1266:CSi
1261:CAl
1256:CMg
1251:CNa
1245:Ne
1216:CBe
1211:CLi
1205:He
1135:doi
1106:doi
1079:doi
1052:doi
998:hdl
990:doi
978:107
943:doi
905:doi
846:doi
813:doi
778:doi
728:".
507:+ "
491:→ 3
475:+ 3
463:to
424:+ I
363:("T
355:("T
159:of
151:(CH
139:(CH
135:),
1865::
1807:No
1802:Md
1797:Fm
1757:CU
1742:Ac
1593:Lr
1513:CW
1469:CI
1399:CY
1315:CV
1293:CK
1276:CS
1271:CP
1241:CF
1236:CO
1231:CN
1226:CC
1221:CB
1195:CH
1129:.
1102:19
1100:.
1075:51
1073:.
1048:13
1046:.
1006:.
996:.
988:.
976:.
972:.
949:.
939:68
937:.
852:.
819:.
811:.
799:36
797:.
720:.
628:KI
564:OH
552:O)
544:(C
518:PO
496:CH
489:OH
480:CH
471:PI
467::
452:.
377:.
328:(T
305:(T
241:.
225:,
218:.
108:.
41:,
1172:e
1165:t
1158:v
1142:.
1137::
1131:9
1112:.
1108::
1085:.
1081::
1059:.
1054::
1029:.
1014:.
1000::
992::
984::
957:.
945::
907::
862:.
848::
827:.
815::
780::
726:I
684:2
680:N
676:+
671:+
667:K
663:+
660:I
652:5
648:H
639:6
635:C
625:+
620:+
615:2
611:N
602:5
598:H
589:6
585:C
562:5
560:H
558:6
554:2
550:5
548:H
546:6
542:3
528:"
523:3
514:3
509:H
505:I
501:3
485:3
473:3
430:2
426:2
422:2
412:2
410:I
403:2
365:3
357:4
330:3
313:.
307:4
290:.
153:3
145:2
143:I
141:2
133:3
106:2
94:3
20:)
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