2248:
2099:
2167:
2004:
42:
575:
35:
963:
181:, which are of particular concern to human and environmental health, are produced in the high temperature environment of forest fires and have been found in the preserved ashes of lightning-ignited fires that predate synthetic dioxins. In addition, a variety of simple chlorinated hydrocarbons including
90:
with one or more hydrogens substituted by chlorine) includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of
1092:
Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006).
1010:, and causes reproductive problems (e.g., eggshell thinning) in certain bird species. DDT also posed further issues to the environment as it is extremely mobile, traces even being found in Antarctica despite the chemical never being used there. Some organochlorine compounds, such as
1029:
However, the presence of chlorine in an organic compound does not ensure toxicity. Some organochlorides are considered safe enough for consumption in foods and medicines. For example, peas and broad beans contain the natural chlorinated plant hormone
586:
Alkyl chlorides are versatile building blocks in organic chemistry. While alkyl bromides and iodides are more reactive, alkyl chlorides tend to be less expensive and more readily available. Alkyl chlorides readily undergo attack by nucleophiles.
889:. Sodium ions leak through the nerve membrane and create a destabilizing negative "afterpotential" with hyperexcitability of the nerve. This leakage causes repeated discharges in the neuron either spontaneously or after a single stimulus.
212:, it is no longer a subject of research for potential therapeutic uses. The frogs obtain epibatidine through their diet which is then sequestered into their skin. Likely dietary sources are beetles, ants, mites, and flies.
471:
129:
due to the higher atomic weight of chlorine versus hydrogen. They have higher boiling and melting points compared to related hydrocarbons. Flammability reduces with increased chlorine substitution in hydrocarbons.
1357:
Elizabeth Norton Lasley (1999). "Having Their Toxins and Eating Them Too Study of the natural sources of many animals' chemical defenses is providing new insights into nature's medicine chest".
149:
Many organochlorine compounds have been isolated from natural sources ranging from bacteria to humans. Chlorinated organic compounds are found in nearly every class of biomolecules and
1038:(Splenda) is widely used in diet products. As of 2004, at least 165 organochlorides had been approved worldwide for use as pharmaceutical drugs, including the natural antibiotic
994:
Some types of organochlorides have significant toxicity to plants or animals, including humans. Dioxins, produced when organic matter is burned in the presence of chlorine, are
232:
alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control. Aryl chlorides may be prepared by the
1095:
1166:
978:(PCBs) were once commonly used electrical insulators and heat transfer agents. Their use has generally been phased out due to health concerns. PCBs were replaced by
1682:
1655:
348:
Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides. In the laboratory, the related reaction involving
362:
1002:). For example, DDT, which was widely used to control insects in the mid-20th century, also accumulates in food chains, as do its metabolites
1656:"The oxidation of chlorinated hydrocarbons" article from The Institute for Green Oxidation Chemistry at the Carnegie Mellon University website
1534:
1430:
1675:
920:(CNS) activity, followed by hyperexcitability, tremors, and then seizures. The mechanism of action is the insecticide binding at the
1341:
1131:
Claudia Wagner, Mustafa El Omari, Gabriele M. König (2009). "Biohalogenation: Nature's Way to
Synthesize Halogenated Metabolites".
1599:
Magnus, Volker; Ozga, Jocelyn A; Reinecke, Dennis M; Pierson, Gerald L; Larue, Thomas A; Cohen, Jerry D; Brenner, Mark L (1997).
1003:
92:
696:) may be used as alkylating agents in production of alkyl compounds. In the case of ethyl chloride, which was used to produce
1668:
1112:
1007:
979:
178:
251:, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.
1458:"Mechanisms of toxic action and structure-activity relationships for organochlorine and synthetic pyrethroid insecticides"
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1031:
995:
481:
1319:
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In the laboratory, thionyl chloride is especially convenient, because the byproducts are gaseous. Alternatively, the
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Several billion kilograms of chlorinated methanes are produced annually, mainly by chlorination of methane:
654:
are possible as well. In the presence of a strong base, alkyl chlorides undergo dehydrohalogenation to give
125:
modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than
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1997:
1992:
1980:
1960:
1950:
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1846:
1787:
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The most important is dichloromethane, which is mainly used as a solvent. Chloromethane is a precursor to
517:
254:
Chlorine adds to the multiple bonds on alkenes and alkynes as well, giving di- or tetra-chloro compounds.
1552:"Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development"
1985:
1797:
1732:
1722:
1160:
836:
122:
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1861:
1841:
1422:
1247:
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1965:
780:
751:. The annual production in 1985 was around 13 million tons, almost all of which was converted into
208:
effects and has stimulated research into new pain medication. However, because of its unacceptable
197:
in the environment is produced naturally by biological decomposition, forest fires, and volcanoes.
103:
998:
which pose dangers when they are released into the environment, as are some insecticides (such as
1281:
Gribble, G. W. (1996). "Naturally occurring organohalogen compounds - A comprehensive survey".
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1651:"Formation of Chlorinated Hydrocarbons in Weathering Plant Material" article at SLAC website
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134:
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Gordon W. Gribble (1999). "The diversity of naturally occurring organobromine compounds".
1023:
983:
787:; they are therefore immiscible with water and effective in cleaning applications such as
764:
299:
182:
150:
107:
302:, hydrogen chloride instead of the more expensive chlorine is used for the same purpose:
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17:
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835:. Historically significant, but smaller in scale is chloroform, mainly a precursor to
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2337:
1224:
674:
477:
349:
194:
138:
75:
1209:
Kjeld C. Engvild (1986). "Chlorine-Containing
Natural Compounds in Higher Plants".
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792:
678:
639:
267:
1104:
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951:
862:
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41:
931:(GABA) chloride ionophore complex, which inhibits chloride flow into the nerve.
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913:
905:
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237:
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50:
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are commonly used as solvents and are referred to as "chlorinated solvents".
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603:
574:
205:
166:
1585:
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1152:
466:{\displaystyle {\ce {{R-OH}+HCl->{\overset {alkyl\ halide}{R-Cl}}+H2O}}}
1491:
1302:
1238:
Gribble, G. W. (1994). "The
Natural production of chlorinated compounds".
1019:
897:
832:
747:
The largest application of organochlorine chemistry is the production of
599:
271:
266:(HCl) to give alkyl chlorides. For example, the industrial production of
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1550:
Pless, Tanja; Boettger, Michael; Hedden, Peter; Graebe, Jan (1984).
396:
492:
Alkyl chlorides are most easily prepared by treating alcohols with
27:
Organic compound with at least 1 covalently bonded atom of chlorine
961:
939:
708:
643:
627:
623:
615:
607:
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337:
126:
962:
705:
630:. Alkyl chlorides are substituted by softer halides such as the
229:
1664:
1384:
795:. They are mostly nonflammable or have very low flammability.
999:
866:
763:
Most low molecular weight chlorinated hydrocarbons such as
885:, they prevent gate closure after activation and membrane
783:
are useful solvents. These solvents tend to be relatively
1637:
MDL Drug Data Report (MDDR), Elsevier MDL, version 2004.2
966:
Structure of mirex, a perchlorocarbon used as a pesticide
456:
408:
193:
have been isolated from marine algae. A majority of the
1601:"4-chloroindole-3-acetic and indole-3-acetic acids in
1413:
Jewkes, John; Sawers, David; Richard, Richard (1969).
1283:
Progress in the
Chemistry of Organic Natural Products
685:
reductively couples two alkyl halides to couple with
365:
29:
2329:
204:, an alkaloid isolated from tree frogs, has potent
1414:
1322:, Agency for Toxic Substances and Disease Registry
465:
1421:(2nd ed.). New York: W. W. Norton. pp.
508:), but also commonly with sulfuryl chloride (SO
1506:Ullmann's Encyclopedia of Industrial Chemistry
1096:Ullmann's Encyclopedia of Industrial Chemistry
873:. Their mechanism of action differs slightly.
32:
1676:
916:. A 2- to 8-hour exposure leads to depressed
8:
1165:: CS1 maint: multiple names: authors list (
847:which is used in the manufacture of Teflon.
1683:
1669:
1661:
1054:(Lamictal), and the inhalation anesthetic
982:(PBDEs), which bring similar toxicity and
1695:with other elements in the periodic table
1622:
1575:
1481:
1087:
1085:
1083:
958:, depending on their molecular structure.
455:
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364:
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1449:
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1316:Public Health Statement - Chloromethane
1079:
141:, which can result in cellular damage.
1712:
1504:Robert L. Metcalf "Insect Control" in
1158:
861:The two main groups of organochlorine
622:. Alkyl chlorides readily react with
91:profound environmental concern, with
7:
2354:Academic research, no widespread use
1240:Environmental Science and Technology
869:-type compounds and the chlorinated
133:Aliphatic organochlorides are often
62:is concerned with the properties of
877:The DDT like compounds work on the
857:Insecticide § Organochlorides
392:
25:
1529:. Blackwell Science. p. 68.
1525:Connell, D.; et al. (1999).
1462:Environmental Health Perspectives
95:being one of the most notorious.
2246:
2165:
2097:
2002:
1702:
892:Chlorinated cyclodienes include
573:
480:, this mixture was once used in
118:Physical and chemical properties
40:
33:
1046:(Claritin), the antidepressant
258:Reaction with hydrogen chloride
1034:(4-Cl-IAA); and the sweetener
980:polybrominated diphenyl ethers
692:Some organochlorides (such as
598:gives alcohols. Reaction with
1:
1624:10.1016/S0031-9422(97)00229-X
1527:Introduction to Ecotoxicology
1105:10.1002/14356007.a06_233.pub2
1050:(Zoloft), the anti-epileptic
996:persistent organic pollutants
1508:Wiley-VCH, Wienheim, 2002.
1225:10.1016/0031-9422(86)80002-4
1093:"Chlorinated Hydrocarbons".
1032:4-chloroindole-3-acetic acid
482:qualitative organic analysis
270:proceeds by the reaction of
1371:10.1525/bisi.1999.49.12.945
1320:Centers for Disease Control
665:Alkyl chlorides react with
590:Heating alkyl halides with
234:Friedel-Crafts halogenation
200:The natural organochloride
2397:
854:
612:Williamson ether synthesis
484:for classifying alcohols.
2243:
2162:
1714:
1710:
1700:
976:Polychlorinated biphenyls
879:peripheral nervous system
488:Other chlorinating agents
137:as chlorine can act as a
1514:10.1002/14356007.a14_263
1417:The sources of invention
1183:Chemical Society Reviews
502:phosphorus pentachloride
98:Organochlorides such as
74:containing at least one
64:organochlorine compounds
60:Organochlorine chemistry
18:Chlorinated hydrocarbons
1456:J R Coats (July 1990).
1099:. Weinheim: Wiley-VCH.
1026:due to their toxicity.
950:. These can be either
934:Other examples include
929:gamma-aminobutyric acid
700:, it is reacted with a
236:, using chlorine and a
49:Two representations of
2349:Many uses in chemistry
2344:Core organic chemistry
1332:Schwarcz, Joe (2012).
967:
918:central nervous system
638:. Reaction with other
518:phosphorus trichloride
467:
413:
965:
837:chlorodifluoromethane
468:
387:
247:, using chlorine and
1042:, the antihistamine
636:Finkelstein reaction
626:to give substituted
363:
191:carbon tetrachloride
1568:10.1104/pp.74.2.320
1474:10.1289/ehp.9087255
1334:The Right Chemistry
1295:10.1021/np50088a001
1260:10.1021/es00056a712
1252:1994EnST...28..310G
1022:, are even used as
781:tetrachloroethylene
458:
412:
410:
395:
262:Alkenes react with
104:tetrachloroethylene
968:
673:, transforming an
463:
446:
398:
145:Natural occurrence
2368:
2367:
2324:
2323:
1536:978-0-632-03852-7
1432:978-0-393-00502-8
1400:10.1021/om030621b
1394:(25): 5154–5178.
1145:10.1021/np800651m
1016:nitrogen mustards
948:pentachlorophenol
881:. At the axon's
845:tetrafluoroethene
777:trichloroethylene
753:polyvinylchloride
671:Grignard reagents
461:
449:
441:
439:
436:
433:
428:
420:
401:
385:
378:
370:
354:hydrochloric acid
264:hydrogen chloride
245:haloform reaction
210:therapeutic index
135:alkylating agents
100:trichloroethylene
76:covalently bonded
72:organic compounds
57:
56:
16:(Redirected from
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1556:Plant Physiology
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1336:. Random House.
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1196:10.1039/a900201d
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1119:
1118:
1089:
1024:chemical weapons
773:dichloroethylene
677:compound into a
614:; reaction with
592:sodium hydroxide
577:
494:thionyl chloride
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151:natural products
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1387:Organometallics
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984:bioaccumulation
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765:dichloromethane
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734:+ 4 NaCl + 3 Pb
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68:organochlorides
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1645:External links
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1617:(4): 675–681.
1610:Phytochemistry
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1212:Phytochemistry
1201:
1190:(5): 335–346.
1172:
1139:(3): 540–553.
1120:
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1068:Organic halide
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887:depolarization
883:sodium channel
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799:Chloromethanes
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749:vinyl chloride
744:
743:Vinyl chloride
741:
739:
736:
731:
727:
723:
719:
715:
713:
698:tetraethyllead
694:ethyl chloride
683:Wurtz reaction
681:compound. The
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567:Appel reaction
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291:
287:
283:
279:
259:
256:
222:
219:
217:
214:
146:
143:
119:
116:
55:
54:
46:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2393:
2382:
2379:
2378:
2376:
2357:
2352:
2347:
2342:
2339:
2336:
2335:
2332:
2328:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2277:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2257:
2255:
2252:
2245:
2242:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2164:
2161:
2157:
2156:
2152:
2149:
2146:
2143:
2140:
2137:
2134:
2131:
2128:
2125:
2122:
2119:
2117:
2114:
2111:
2108:
2106:
2103:
2096:
2094:
2091:
2088:
2087:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2008:
2001:
1999:
1996:
1994:
1991:
1990:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1905:
1902:
1900:
1897:
1896:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1811:
1808:
1806:
1803:
1802:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1760:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1720:
1716:
1708:
1705:
1704:
1699:
1694:
1691:Compounds of
1686:
1681:
1679:
1674:
1672:
1667:
1666:
1663:
1657:
1654:
1652:
1649:
1648:
1644:
1634:
1631:
1625:
1620:
1616:
1612:
1611:
1606:
1604:
1603:Pisum sativum
1595:
1592:
1587:
1583:
1578:
1573:
1569:
1565:
1561:
1557:
1553:
1546:
1543:
1538:
1532:
1528:
1521:
1518:
1515:
1511:
1507:
1501:
1498:
1493:
1489:
1484:
1479:
1475:
1471:
1467:
1463:
1459:
1452:
1450:
1446:
1434:
1428:
1424:
1419:
1418:
1409:
1406:
1401:
1397:
1393:
1389:
1388:
1380:
1377:
1372:
1368:
1364:
1360:
1353:
1350:
1345:
1343:9780385671606
1339:
1335:
1328:
1325:
1321:
1317:
1312:
1309:
1304:
1300:
1296:
1292:
1289:(10): 1–423.
1288:
1284:
1277:
1274:
1269:
1265:
1261:
1257:
1253:
1249:
1245:
1241:
1234:
1231:
1226:
1222:
1218:
1214:
1213:
1205:
1202:
1197:
1193:
1189:
1185:
1184:
1176:
1173:
1168:
1162:
1154:
1150:
1146:
1142:
1138:
1134:
1127:
1125:
1121:
1116:
1110:
1106:
1102:
1098:
1097:
1088:
1086:
1084:
1080:
1073:
1069:
1066:
1065:
1061:
1059:
1057:
1053:
1049:
1045:
1041:
1037:
1033:
1027:
1025:
1021:
1017:
1013:
1009:
1005:
1001:
997:
989:
987:
985:
981:
977:
970:
964:
957:
953:
949:
945:
941:
937:
933:
930:
926:
919:
915:
911:
907:
903:
899:
895:
891:
888:
884:
880:
876:
875:
874:
872:
868:
864:
858:
850:
848:
846:
838:
834:
830:
829:chlorosilanes
806:
805:
804:
798:
796:
794:
790:
786:
782:
778:
774:
770:
766:
758:
756:
754:
750:
742:
737:
714:4 NaPb + 4 CH
712:
710:
707:
703:
699:
695:
690:
688:
684:
680:
676:
675:electrophilic
672:
668:
663:
661:
657:
653:
649:
645:
641:
640:pseudohalides
637:
633:
629:
625:
621:
617:
613:
609:
605:
601:
597:
593:
588:
581:
576:
572:
571:
570:
569:can be used:
568:
552:
538:
527:
526:
525:
519:
503:
495:
487:
485:
483:
479:
478:Lucas reagent
451:
443:
422:
403:
388:
380:
372:
359:
358:
357:
355:
351:
350:zinc chloride
343:
305:
304:
303:
301:
277:
276:
275:
273:
269:
265:
257:
255:
252:
250:
246:
241:
239:
235:
231:
227:
221:From chlorine
220:
215:
213:
211:
207:
203:
198:
196:
195:chloromethane
192:
188:
184:
180:
176:
172:
168:
164:
160:
156:
152:
144:
142:
140:
139:leaving group
136:
131:
128:
124:
117:
115:
113:
109:
105:
101:
96:
94:
89:
85:
81:
77:
73:
69:
65:
61:
52:
48:
47:
43:
36:
31:
19:
2359:Bond unknown
1792:
1633:
1614:
1608:
1602:
1594:
1562:(2): 320–3.
1559:
1555:
1545:
1526:
1520:
1505:
1500:
1465:
1461:
1436:. Retrieved
1416:
1408:
1391:
1385:
1379:
1362:
1358:
1352:
1333:
1327:
1311:
1286:
1282:
1276:
1243:
1239:
1233:
1216:
1210:
1204:
1187:
1181:
1175:
1161:cite journal
1136:
1133:J. Nat. Prod
1132:
1094:
1028:
993:
974:
927:site in the
863:insecticides
860:
826:
802:
793:dry cleaning
762:
746:
738:Applications
691:
679:nucleophilic
664:
589:
585:
564:
557:→ RCl + POCl
491:
475:
347:
297:
268:chloroethane
261:
253:
242:
224:
199:
148:
132:
123:Chlorination
121:
97:
84:chloroalkane
83:
67:
63:
59:
58:
1468:: 255–262.
1052:lamotrigine
986:concerns.
956:hydrophobic
952:hydrophilic
652:thiocyanate
543:→ 3 RCl + H
539:3 ROH + PCl
476:Called the
216:Preparation
202:epibatidine
175:fatty acids
163:amino acids
1359:BioScience
1114:3527306730
1074:References
1056:isoflurane
1048:sertraline
1044:loratadine
1040:vancomycin
971:Insulators
914:endosulfan
906:heptachlor
871:alicyclics
855:See also:
851:Pesticides
789:degreasing
769:chloroform
722:Cl → Pb(CH
620:thioethers
604:aryloxides
532:→ RCl + SO
528:ROH + SOCl
314:+ 2 HCl +
286:+ HCl → CH
274:with HCl:
240:catalyst.
238:Lewis acid
187:chloroform
167:flavonoids
153:including
112:chloroform
51:chloroform
2340:to carbon
1036:sucralose
910:chlordane
833:silicones
785:non-polar
667:magnesium
600:alkoxides
582:Reactions
553:ROH + PCl
423:−
393:Δ
373:−
206:analgesic
155:alkaloids
2375:Category
1586:16663416
1268:22662801
1153:19245259
1062:See also
1020:Lewisite
990:Toxicity
898:dieldrin
865:are the
759:Solvents
669:to give
642:such as
389:→
272:ethylene
171:steroids
159:terpenes
80:chlorine
78:atom of
2158:
1577:1066676
1492:2176589
1483:1567810
1438:11 July
1303:8795309
1248:Bibcode
936:dicofol
823:+ x HCl
755:(PVC).
660:alkynes
656:alkenes
648:cyanide
634:in the
610:in the
319:⁄
226:Alkanes
179:Dioxins
88:alkanes
86:class (
2330:Legend
1693:carbon
1584:
1574:
1533:
1490:
1480:
1429:
1425:–237.
1340:
1301:
1266:
1151:
1111:
1018:, and
946:, and
944:kepone
902:endrin
894:aldrin
843:) and
839:(CHClF
811:+ x Cl
702:sodium
687:sodium
650:, and
632:iodide
628:amines
624:amines
616:thiols
608:ethers
516:) and
438:halide
435:
328:→ ClCH
189:, and
173:, and
82:. The
940:mirex
709:alloy
644:azide
618:give
606:give
596:water
561:+ HCl
536:+ HCl
500:) or
496:(SOCl
432:alkyl
336:Cl +
127:water
66:, or
1582:PMID
1531:ISBN
1488:PMID
1440:2018
1427:ISBN
1338:ISBN
1299:PMID
1264:PMID
1167:link
1149:PMID
1109:ISBN
1006:and
922:GABA
912:and
831:and
815:→ CH
791:and
779:and
706:lead
520:(PCl
504:(PCl
400:ZnCl
282:C=CH
243:The
230:aryl
228:and
110:and
93:TCDD
2304:CEs
2299:CCf
2294:CBk
2289:CCm
2284:CAm
2279:CPu
2274:CNp
2264:CPa
2259:CTh
2238:CYb
2233:CTm
2228:CEr
2223:CHo
2218:CDy
2213:CTb
2208:CGd
2203:CEu
2198:CSm
2193:CPm
2188:CNd
2183:CPr
2178:CCe
2173:CLa
2153:Og
2150:Ts
2147:Lv
2144:Mc
2141:Fl
2138:Nh
2135:Cn
2132:Rg
2129:Ds
2126:Mt
2123:Hs
2120:Bh
2116:CSg
2112:Db
2109:Rf
2093:CRa
2089:Fr
2084:Rn
2080:CAt
2075:CPo
2070:CBi
2065:CPb
2060:CTl
2055:CHg
2050:CAu
2045:CPt
2040:CIr
2035:COs
2030:CRe
2020:CTa
2015:CHf
2010:CLu
1998:CBa
1993:CCs
1986:CXe
1976:CTe
1971:CSb
1966:CSn
1961:CIn
1956:CCd
1951:CAg
1946:CPd
1941:CRh
1936:CRu
1931:CTc
1926:CMo
1921:CNb
1916:CZr
1904:CSr
1899:CRb
1892:CKr
1887:CBr
1882:CSe
1877:CAs
1872:CGe
1867:CGa
1862:CZn
1857:CCu
1852:CNi
1847:CCo
1842:CFe
1837:CMn
1832:CCr
1822:CTi
1817:CSc
1810:CCa
1798:CAr
1793:CCl
1778:CSi
1773:CAl
1768:CMg
1763:CNa
1757:Ne
1728:CBe
1723:CLi
1717:He
1619:doi
1572:PMC
1564:doi
1510:doi
1478:PMC
1470:doi
1423:235
1396:doi
1367:doi
1291:doi
1256:doi
1221:doi
1192:doi
1141:doi
1101:doi
1008:DDD
1004:DDE
1000:DDT
954:or
867:DDT
817:4−x
658:or
602:or
594:or
524:):
384:HCl
310:=CH
298:In
2377::
2319:No
2314:Md
2309:Fm
2269:CU
2254:Ac
2105:Lr
2025:CW
1981:CI
1911:CY
1827:CV
1805:CK
1788:CS
1783:CP
1753:CF
1748:CO
1743:CN
1738:CC
1733:CB
1707:CH
1615:46
1613:.
1607:.
1580:.
1570:.
1560:74
1558:.
1554:.
1486:.
1476:.
1466:87
1464:.
1460:.
1448:^
1392:22
1390:.
1363:45
1361:.
1318:,
1297:.
1287:68
1285:.
1262:.
1254:.
1244:28
1242:.
1217:25
1215:.
1188:28
1186:.
1163:}}
1159:{{
1147:.
1137:72
1135:.
1123:^
1107:.
1082:^
1058:.
1014:,
942:,
938:,
908:,
904:,
900:,
896:,
819:Cl
807:CH
775:,
771:,
767:,
726:CH
718:CH
711::
689:.
662:.
646:,
547:PO
512:Cl
427:Cl
377:OH
356::
332:CH
306:CH
294:Cl
290:CH
185:,
177:.
169:,
165:,
161:,
157:,
106:,
102:,
70:,
53:.
1684:e
1677:t
1670:v
1627:.
1621::
1605:"
1588:.
1566::
1539:.
1512::
1494:.
1472::
1442:.
1402:.
1398::
1373:.
1369::
1346:.
1305:.
1293::
1270:.
1258::
1250::
1227:.
1223::
1198:.
1194::
1169:)
1155:.
1143::
1117:.
1103::
924:A
841:2
821:x
813:2
809:4
732:4
730:)
728:2
724:3
720:2
716:3
704:–
559:3
555:5
549:3
545:3
541:3
534:2
530:2
522:3
514:2
510:2
506:5
498:2
460:O
452:2
448:H
444:+
419:R
404:2
381:+
369:R
344:.
342:O
340:2
338:H
334:2
330:2
326:2
324:O
321:2
317:1
312:2
308:2
292:2
288:3
284:2
280:2
278:H
20:)
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