289:
to the seven carbons, and "-ane", indicating single bonding between carbons. Next, the numerical prefix is added in front of the base name, representing the number of carbons in each ring (excluding the shared carbons) and the number of carbons present in the bridge between the rings. In this example, there are two rings with two carbons each and a single bridge with one carbon, excluding the carbons shared by both the rings. The prefix consists of three numbers that are arranged in descending order, separated by dots: . Before the numerical prefix is another prefix indicating the number of rings (e.g., "bicyclo+"). Thus, the name is bicycloheptane.
828:
265:-"), and a numeric prefix before that indicating the number of carbons in each part of each ring, exclusive of junctions. For instance, a bicyclooctane that consists of a six-membered ring and a four-membered ring, which share two adjacent carbon atoms that form a shared edge, is -bicyclooctane. That part of the six-membered ring, exclusive of the shared edge has 4 carbons. That part of the four-membered ring, exclusive of the shared edge, has 2 carbons. The edge itself, exclusive of the two vertices that define it, has 0 carbons.
812:
637:. At these ring sizes, one or more of these sources of strain must be present, resulting in an increase in strain energy, which peaks at 9 carbons (around 50 kJ mol). After that, strain energy slowly decreases until 12 carbon atoms, where it drops significantly; at 14, another significant drop occurs and the strain is on a level comparable with 10 kJ mol. At larger ring sizes there is little or no strain since there are many accessible conformations corresponding to a diamond lattice.
20:
786:
192:
672:
273:, because this system is constantly being revised. In the above example -bicyclooctane would be written bicyclooctane to fit the conventions for IUPAC naming. It then has room for an additional numerical prefix if there is the need to include details of other attachments to the molecule such as chlorine or a methyl group. Another convention for the naming of compounds is the
586:
of 109° 28′ whenever possible. Owing to evident geometrical reasons, rings with 3, 4, and (to a small extent) also 5 atoms can only afford narrower angles; the consequent deviation from the ideal tetrahedral bond angles causes an increase in potential energy and an overall destabilizing effect.
288:
The IUPAC naming system for organic compounds can be demonstrated using the example provided in the adjacent image. The base name of the compound, indicating the total number of carbons in both rings (including the shared edge), is listed first. For instance, "heptane" denotes "hepta-", which refers
616:
the C–C–C bond angles would be 108°, very close to the measure of the tetrahedral angle. Actual cyclopentane molecules are puckered, but this changes only the bond angles slightly so that angle strain is relatively small. The eclipsing interactions are also reduced, leaving a ring strain of about
268:
There is more than one convention (method or nomenclature) for the naming of compounds, which can be confusing for those who are just learning, and inconvenient for those who are well-rehearsed in the older ways. For beginners, it is best to learn IUPAC nomenclature from
628:
of cyclohexane, axial hydrogens on adjacent carbon atoms are pointed in opposite directions, virtually eliminating eclipsing strain. In medium-sized rings (7 to 13 carbon atoms) conformations in which the angle strain is minimised create
608:
has the carbon atoms in a puckered square with approximately 90° bond angles; "puckering" reduces the eclipsing interactions between hydrogen atoms. Its ring strain is therefore slightly less, at around 110 kJ mol.
602:, in which the carbon atoms form a triangle and therefore have 60 °C–C–C bond angles. There are also three pairs of eclipsed hydrogens. The ring strain is calculated to be around 120 kJ mol.
664:
Cycloalkanes, referred to as naphthenes, are a major substrate for the catalytic reforming process. In the presence of a catalyst and at temperatures of about 495 to 525 °C, naphthenes undergo
595:
of the cycloalkane with the value calculated using average bond energies. Molecular mechanics calculations are well suited to identify the many conformations occurring particularly in medium rings.
206:
Unsubstituted cycloalkanes that contain a single ring in their molecular structure are typically named by adding the prefix "cyclo" to the name of the corresponding linear
624:
the ring strain and eclipsing interactions are negligible because the puckering of the ring allows ideal tetrahedral bond angles to be achieved. In the most stable
1993:
1575:
1514:
1983:
1978:
1499:
1965:
1486:
1557:
1175:
873:
656:, is noted for being one of the most strained compounds that is isolatable on a large scale; its strain energy is estimated at 267 kJ mol.
776:
Numerous methods exist for preparing cycloalkanes by ring-closing reactions of difunctional precursors. For example, diesters are cyclized in the
2005:
1526:
2051:
557:
because the ring shape allows for a larger area of contact. Containing only C–C and C–H bonds, unreactivity of cycloalkanes with little or no
2066:
2061:
2046:
1631:
257:
alkanes is more complex, with the base name indicating the number of carbons in the ring system, a prefix indicating the number of rings ( "
2135:
2104:
1883:
1873:
1758:
2140:
2119:
2114:
1898:
1893:
1888:
1878:
1773:
1768:
1763:
1753:
1419:
583:
1167:
Michael Tuttle Musser "Cyclohexanol and
Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
2727:
1260:
592:
281:, the name of which can tell us only that it is an alcohol (because the suffix "-ol" is in the name) and it should then have a
591:
of a cycloalkane is the increase in energy caused by the compound's geometry, and is calculated by comparing the experimental
973:
827:
754:
50:
1152:
1087:
835:
The corresponding cycloaddition reactions, which usually require photochemical activation, result in cyclobutanes.
2185:
806:) more elaborate methods are required since intramolecular ring closure competes with intermolecular reactions.
1043:
1229:
1198:
Organic
Chemistry IUPAC Nomenclature. Rule A-23. Hydrogenated Compounds from Fused Polycyclic Hydrocarbons
785:
277:, which is a shorter name and it gives less information about the compound. An example of a common name is
2720:
1253:
1233:
993:
906:
588:
128:
includes also those saturated hydrocarbons that are polycyclic. In any case, the general form of the
1106:; Lampman, G. M.; Ciula, R. P.; Connor, D. S.; Schertler, P.; Lavanish, J. (1965). "Bicyclobutane".
849:
955:
1645:
726:, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of
2595:
1409:
777:
750:
541:
Cycloalkanes are similar to alkanes in their general physical properties, but they have higher
1216:
Organic
Chemistry IUPAC Nomenclature.Rules A-51, A-52, A-53, A-54:Hydrocarbon Ring Assemblies
1063:
2823:
2713:
2656:
2590:
1246:
1108:
579:
2174:
1973:
1217:
1211:
1205:
821:
796:
738:
1199:
8:
2502:
630:
1204:
Organic
Chemistry IUPAC Nomenclature.Rule A-31. Bridged Hydrocarbons: Bicyclic Systems.
2689:
2646:
1504:
1494:
1016:
570:
180:
1121:
2580:
2552:
2395:
2155:
2150:
1988:
1509:
1148:
1103:
1083:
1059:
1039:
969:
758:
737:
The small cycloalkanes – in particular, cyclopropane – have a lower stability due to
641:
250:
31:
1185:
1020:
883:
2802:
2544:
1189:
1180:
1140:
1117:
1008:
961:
887:
878:
803:
129:
47:
2694:
2651:
2560:
2434:
1399:
1389:
665:
270:
158:
is the number of rings. The simpler form for cycloalkanes with only one ring is C
72:. The larger cycloalkanes, with more than 20 carbon atoms are typically called
214:
atoms in its chain as the cycloalkane has in its ring. For example, the name of
2797:
2625:
2620:
2585:
2536:
2442:
1414:
1404:
1079:
769:
Many simple cycloalkanes are obtained from petroleum. They can be produced by
587:
Eclipsing of hydrogen atoms is an important destabilizing effect, as well. The
282:
254:
114:
19:
1012:
671:
2817:
2792:
2787:
2302:
2109:
2099:
1595:
1144:
844:
770:
723:
645:
634:
554:
546:
542:
1193:
965:
891:
2767:
2757:
2747:
2408:
2372:
2268:
2041:
2031:
1940:
1930:
1920:
1461:
1451:
1441:
757:. These reactions are ring-opening reactions or ring-cleavage reactions of
613:
599:
436:
384:
333:
215:
106:
98:
90:
53:
1210:
Organic
Chemistry IUPAC Nomenclature.Rules A-41, A-42: Spiro Hydrocarbons
811:
2782:
2777:
2772:
2762:
2752:
2456:
2413:
2386:
2320:
2283:
2202:
2056:
2036:
2023:
1955:
1950:
1945:
1935:
1925:
1912:
1743:
1476:
1471:
1466:
1456:
1446:
1269:
930:
854:
742:
727:
687:
621:
605:
558:
514:
488:
462:
410:
358:
191:
110:
102:
94:
69:
65:
43:
24:
2515:
2403:
2207:
2094:
2084:
2013:
1748:
1570:
1565:
1540:
1394:
1384:
195:
1184:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (1995) "
882:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2014) "
64:
atoms arranged in a structure containing a single ring (possibly with
2520:
2258:
2227:
2217:
2212:
2089:
1817:
1605:
1600:
1379:
683:
682:
In another major industrial process, cyclohexanol is produced by the
297:
278:
2684:
2679:
2489:
2481:
2473:
2353:
2345:
2337:
2288:
2273:
2263:
2253:
2248:
2222:
2145:
1857:
1837:
1687:
1615:
1610:
1590:
691:
57:
2641:
2615:
2465:
2310:
2243:
1842:
1832:
1822:
1712:
1702:
1692:
1580:
1546:
1534:
1348:
1338:
1328:
1318:
746:
550:
227:
186:
79:
2705:
2510:
2429:
2329:
2278:
1852:
1847:
1827:
1787:
1727:
1722:
1717:
1707:
1697:
1658:
1585:
1363:
1358:
1353:
1343:
1333:
1323:
1288:
1238:
243:
239:
211:
207:
61:
2194:
2160:
2076:
1135:
Irion, Walther W.; Neuwirth, Otto S. (2000). "Oil
Refining".
1038:(5th ed.). Pacific Grove, CA: Brooks/Cole. p. 126.
731:
121:
679:
The process provides a way to produce high octane gasoline.
1218:
http://www.acdlabs.com/iupac/nomenclature/79/r79_158.htm
1212:
http://www.acdlabs.com/iupac/nomenclature/79/r79_196.htm
1206:
http://www.acdlabs.com/iupac/nomenclature/79/r79_163.htm
1102:
1200:
http://www.acdlabs.com/iupac/nomenclature/79/r79_73.htm
824:, a cycloaddition, provides a route to cyclohexenes:
122:
85:
The cycloalkanes without side chains (also known as
226:) containing a three-membered ring is derived from
561:(see below) are comparable to non-cyclic alkanes.
56:. In other words, a cycloalkane consists only of
2815:
564:
1287:
1137:Ullmann's Encyclopedia of Industrial Chemistry
2721:
1254:
1134:
987:
985:
773:of unsaturated, even aromatic precursors.
991:
2728:
2714:
1261:
1247:
982:
640:Ring strain can be considerably higher in
292:Cycloalkanes as a group are also known as
68:), and all of the carbon-carbon bonds are
1074:. In Hart, H.; Karabatsos, G. J. (eds.).
994:"Conformational analysis of cycloalkanes"
249:The naming of polycyclic alkanes such as
124:(IUPAC), in some authors' usage the term
308:
190:
18:
1033:
953:
2816:
1128:
1058:
593:standard enthalpy change of combustion
575:In cycloalkanes, the carbon atoms are
553:than alkanes. This is due to stronger
2709:
1242:
901:
899:
120:Besides this standard definition by
755:nucleophilic aliphatic substitution
13:
1181:Compendium of Chemical Terminology
957:Fundamentals of Petroleum Refining
896:
879:Compendium of Chemical Terminology
826:
810:
784:
670:
154:is the number of carbon atoms and
78:. All cycloalkanes are isomers of
14:
2835:
1223:
2735:
1268:
328:Liquid density (at 20 °C)
1161:
1076:Advances in Alicyclic Chemistry
954:Fahim, MA, et al. (2010).
690:in air, typically using cobalt
174:
16:Saturated alicyclic hydrocarbon
1096:
1052:
1027:
947:
923:
867:
764:
749:, though they do not react in
668:to give aromatic derivatives:
117:), and large (all the rest).
1:
1122:10.1016/S0040-4020(01)98361-9
860:
582:, which would imply an ideal
565:Conformations and ring strain
303:
992:Dragojlovic, Veljko (2015).
907:"Alkanes & Cycloalkanes"
799:can be deployed similarly.
659:
296:, a term mainly used in the
7:
838:
598:Ring strain is highest for
271:a source that is up to date
89:) are classified as small (
10:
2840:
831:The Dieckmann condensation
789:The Dieckmann condensation
745:. They react similarly to
568:
246:atoms in the main chain.
184:
178:
2743:
2672:
2634:
2608:
2573:
2529:
2501:
2464:
2455:
2422:
2394:
2385:
2365:
2328:
2319:
2301:
2236:
2193:
2184:
2173:
2128:
2075:
2022:
2004:
1964:
1911:
1866:
1810:
1786:
1736:
1680:
1657:
1644:
1624:
1556:
1525:
1485:
1432:
1372:
1311:
1276:
1013:10.1007/s40828-015-0014-0
612:For a theoretical planar
1145:10.1002/14356007.a18_051
1064:"Small Ring Bicyclo[
850:Conformational isomerism
210:with the same number of
23:Ball-and-stick model of
1234:Encyclopædia Britannica
1194:10.1351/goldbook.C01497
966:10.1016/C2009-0-16348-1
892:10.1351/goldbook.C01497
2596:1,3,5-Triheptylbenzene
1034:McMurry, John (2000).
911:www2.chemistry.msu.edu
832:
815:
790:
778:Dieckmann condensation
751:electrophilic addition
676:
584:tetrahedral bond angle
285:(–OH) attached to it.
203:
27:
2591:1,3,5-Triethylbenzene
830:
814:
788:
722:This process coforms
674:
617:25 kJ mol.
309:Table of cycloalkanes
194:
132:for cycloalkanes is C
22:
1994:Isopropylcyclohexene
1576:Perhydrophenanthrene
1515:Isopropylcyclohexane
1082:. pp. 185–254.
822:Diels-Alder reaction
797:acyloin condensation
42:, but distinct from
2690:Alicyclic compounds
2503:Tetramethylbenzenes
631:transannular strain
2647:Cyclopropenylidene
1984:Methylcyclopentene
1974:Methylcyclopropene
1505:Methylcyclopentane
1495:Methylcyclopropane
833:
816:
802:For larger rings (
791:
759:alkyl cycloalkanes
677:
571:Strain (chemistry)
204:
181:IUPAC nomenclature
28:
2811:
2810:
2703:
2702:
2668:
2667:
2604:
2603:
2581:Hexamethylbenzene
2569:
2568:
2451:
2450:
2396:Trimethylbenzenes
2381:
2380:
2297:
2296:
2169:
2168:
2156:Cyclododecatriene
2151:Cyclooctatetraene
1989:Methylcyclohexene
1979:Methylcyclobutene
1966:Alkylcycloalkenes
1907:
1906:
1782:
1781:
1640:
1639:
1510:Methylcyclohexane
1500:Methylcyclobutane
1487:Alkylcycloalkanes
1428:
1427:
1116:(10): 2749–2769.
1036:Organic chemistry
975:978-0-444-52785-1
804:macrocyclizations
539:
538:
32:organic chemistry
2831:
2803:Cyclotetradecane
2730:
2723:
2716:
2707:
2706:
2660:-Propenylbenzene
2462:
2461:
2392:
2391:
2326:
2325:
2317:
2316:
2191:
2190:
2182:
2181:
1867:Branched alkynes
1808:
1807:
1737:Branched alkenes
1678:
1677:
1655:
1654:
1558:Polycycloalkanes
1543:(bicycloheptane)
1537:(bicyclopentane)
1373:Branched alkanes
1309:
1308:
1285:
1284:
1263:
1256:
1249:
1240:
1239:
1168:
1165:
1159:
1158:
1132:
1126:
1125:
1100:
1094:
1093:
1056:
1050:
1049:
1031:
1025:
1024:
998:
989:
980:
979:
951:
945:
944:
942:
941:
935:iupac.qmul.ac.uk
927:
921:
920:
918:
917:
903:
894:
871:
644:. For example,
642:bicyclic systems
313:
312:
130:chemical formula
87:monocycloalkanes
2839:
2838:
2834:
2833:
2832:
2830:
2829:
2828:
2814:
2813:
2812:
2807:
2739:
2734:
2704:
2699:
2695:Petroleum jelly
2664:
2652:Phenylacetylene
2630:
2600:
2565:
2561:Isobutylbenzene
2525:
2497:
2447:
2418:
2377:
2361:
2315:
2293:
2232:
2176:
2165:
2124:
2071:
2018:
2000:
1960:
1903:
1862:
1804:
1796:
1790:
1778:
1732:
1674:
1667:
1661:
1650:
1648:
1636:
1620:
1552:
1549:(bicyclodecane)
1521:
1481:
1424:
1390:3-Methylpentane
1368:
1305:
1297:
1291:
1280:
1278:
1272:
1267:
1226:
1172:
1171:
1166:
1162:
1155:
1133:
1129:
1101:
1097:
1090:
1078:. Vol. 2.
1072:.0]alkanes"
1057:
1053:
1046:
1032:
1028:
996:
990:
983:
976:
952:
948:
939:
937:
929:
928:
924:
915:
913:
905:
904:
897:
872:
868:
863:
841:
767:
730:, used to make
717:
713:
709:
705:
701:
666:dehydrogenation
662:
655:
651:
573:
567:
526:
522:
500:
496:
474:
470:
448:
444:
422:
418:
396:
392:
370:
366:
345:
341:
325:Melting point
322:Boiling point
311:
306:
237:
233:
225:
221:
189:
183:
177:
170:
163:
149:
137:
17:
12:
11:
5:
2837:
2827:
2826:
2809:
2808:
2806:
2805:
2800:
2798:Cyclotridecane
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2744:
2741:
2740:
2733:
2732:
2725:
2718:
2710:
2701:
2700:
2698:
2697:
2692:
2687:
2682:
2676:
2674:
2670:
2669:
2666:
2665:
2663:
2662:
2654:
2649:
2644:
2638:
2636:
2632:
2631:
2629:
2628:
2626:4-Vinyltoluene
2623:
2621:Divinylbenzene
2618:
2612:
2610:
2606:
2605:
2602:
2601:
2599:
2598:
2593:
2588:
2586:2-Phenylhexane
2583:
2577:
2575:
2571:
2570:
2567:
2566:
2564:
2563:
2558:
2550:
2542:
2533:
2531:
2527:
2526:
2524:
2523:
2518:
2513:
2507:
2505:
2499:
2498:
2496:
2495:
2487:
2479:
2470:
2468:
2459:
2453:
2452:
2449:
2448:
2446:
2445:
2443:4-Ethyltoluene
2440:
2438:-Propylbenzene
2432:
2426:
2424:
2420:
2419:
2417:
2416:
2411:
2406:
2400:
2398:
2389:
2383:
2382:
2379:
2378:
2376:
2375:
2369:
2367:
2363:
2362:
2360:
2359:
2351:
2343:
2334:
2332:
2323:
2314:
2313:
2307:
2305:
2299:
2298:
2295:
2294:
2292:
2291:
2286:
2281:
2276:
2271:
2266:
2261:
2256:
2251:
2246:
2240:
2238:
2234:
2233:
2231:
2230:
2225:
2220:
2215:
2210:
2205:
2199:
2197:
2188:
2179:
2171:
2170:
2167:
2166:
2164:
2163:
2158:
2153:
2148:
2143:
2138:
2132:
2130:
2126:
2125:
2123:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2081:
2079:
2073:
2072:
2070:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2028:
2026:
2020:
2019:
2017:
2016:
2010:
2008:
2006:Bicycloalkenes
2002:
2001:
1999:
1998:
1996:
1991:
1986:
1981:
1976:
1970:
1968:
1962:
1961:
1959:
1958:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1917:
1915:
1909:
1908:
1905:
1904:
1902:
1901:
1896:
1891:
1886:
1881:
1876:
1870:
1868:
1864:
1863:
1861:
1860:
1855:
1850:
1845:
1840:
1835:
1830:
1825:
1820:
1814:
1812:
1811:Linear alkynes
1805:
1798:
1792:
1784:
1783:
1780:
1779:
1777:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1740:
1738:
1734:
1733:
1731:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1684:
1682:
1681:Linear alkenes
1675:
1669:
1663:
1652:
1642:
1641:
1638:
1637:
1635:
1634:
1628:
1626:
1622:
1621:
1619:
1618:
1613:
1608:
1603:
1598:
1593:
1588:
1583:
1578:
1573:
1568:
1562:
1560:
1554:
1553:
1551:
1550:
1544:
1538:
1531:
1529:
1527:Bicycloalkanes
1523:
1522:
1520:
1519:
1517:
1512:
1507:
1502:
1497:
1491:
1489:
1483:
1482:
1480:
1479:
1474:
1469:
1464:
1459:
1454:
1449:
1444:
1438:
1436:
1430:
1429:
1426:
1425:
1423:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1387:
1382:
1376:
1374:
1370:
1369:
1367:
1366:
1361:
1356:
1351:
1346:
1341:
1336:
1331:
1326:
1321:
1315:
1313:
1312:Linear alkanes
1306:
1299:
1293:
1282:
1274:
1273:
1266:
1265:
1258:
1251:
1243:
1237:
1236:
1232:at the online
1230:"Cycloalkanes"
1225:
1224:External links
1222:
1221:
1220:
1214:
1208:
1202:
1196:
1170:
1169:
1160:
1153:
1127:
1095:
1088:
1080:Academic Press
1051:
1044:
1026:
981:
974:
960:. p. 14.
946:
922:
895:
865:
864:
862:
859:
858:
857:
852:
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837:
818:
817:
793:
792:
766:
763:
720:
719:
715:
711:
707:
703:
699:
661:
658:
653:
649:
569:Main article:
566:
563:
547:melting points
543:boiling points
537:
536:
533:
530:
527:
524:
520:
517:
511:
510:
507:
504:
501:
498:
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491:
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349:
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329:
326:
323:
320:
317:
310:
307:
305:
302:
283:hydroxyl group
235:
231:
223:
219:
200:bicycloheptane
176:
173:
165:
159:
139:
133:
115:cyclotridecane
75:cycloparaffins
15:
9:
6:
4:
3:
2:
2836:
2825:
2822:
2821:
2819:
2804:
2801:
2799:
2796:
2794:
2793:Cyclododecane
2791:
2789:
2788:Cycloundecane
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
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2742:
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2731:
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2640:
2639:
2637:
2633:
2627:
2624:
2622:
2619:
2617:
2614:
2613:
2611:
2609:Vinylbenzenes
2607:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2578:
2576:
2572:
2562:
2559:
2557:
2556:-Butylbenzene
2555:
2551:
2549:
2548:-Butylbenzene
2547:
2543:
2541:
2540:-Butylbenzene
2539:
2535:
2534:
2532:
2528:
2522:
2519:
2517:
2514:
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2500:
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2331:
2327:
2324:
2322:
2318:
2312:
2309:
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2306:
2304:
2303:Alkylbenzenes
2300:
2290:
2287:
2285:
2282:
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2209:
2206:
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2201:
2200:
2198:
2196:
2192:
2189:
2187:
2183:
2180:
2178:
2172:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2137:
2134:
2133:
2131:
2127:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2083:
2082:
2080:
2078:
2074:
2068:
2065:
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2030:
2029:
2027:
2025:
2021:
2015:
2012:
2011:
2009:
2007:
2003:
1997:
1995:
1992:
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1987:
1985:
1982:
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1623:
1617:
1614:
1612:
1609:
1607:
1604:
1602:
1599:
1597:
1596:Dodecahedrane
1594:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
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1569:
1567:
1564:
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1484:
1478:
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1437:
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1421:
1418:
1416:
1413:
1411:
1408:
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1398:
1396:
1393:
1391:
1388:
1386:
1383:
1381:
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1350:
1347:
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1330:
1327:
1325:
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1320:
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1303:
1296:
1290:
1286:
1283:
1275:
1271:
1264:
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1241:
1235:
1231:
1228:
1227:
1219:
1215:
1213:
1209:
1207:
1203:
1201:
1197:
1195:
1191:
1187:
1183:
1182:
1177:
1174:
1173:
1164:
1156:
1154:3-527-30673-0
1150:
1146:
1142:
1138:
1131:
1123:
1119:
1115:
1111:
1110:
1105:
1104:Wiberg, K. B.
1099:
1091:
1089:9781483224213
1085:
1081:
1077:
1073:
1071:
1067:
1061:
1060:Wiberg, K. B.
1055:
1047:
1041:
1037:
1030:
1022:
1018:
1014:
1010:
1006:
1002:
995:
988:
986:
977:
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959:
958:
950:
936:
932:
926:
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908:
902:
900:
893:
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881:
880:
875:
870:
866:
856:
853:
851:
848:
846:
845:Prelog strain
843:
842:
836:
829:
825:
823:
813:
809:
808:
807:
805:
800:
798:
787:
783:
782:
781:
779:
774:
772:
771:hydrogenation
762:
760:
756:
752:
748:
744:
740:
739:Baeyer strain
735:
733:
729:
725:
724:cyclohexanone
697:
696:
695:
693:
689:
685:
680:
673:
669:
667:
657:
647:
646:bicyclobutane
643:
638:
636:
635:Pitzer strain
632:
627:
623:
618:
615:
610:
607:
603:
601:
596:
594:
590:
589:strain energy
585:
581:
578:
572:
562:
560:
556:
555:London forces
552:
548:
544:
534:
531:
528:
518:
516:
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512:
508:
505:
502:
492:
490:
487:
486:
482:
479:
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460:
456:
453:
450:
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438:
435:
434:
430:
427:
424:
414:
412:
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401:
398:
388:
386:
383:
382:
378:
375:
372:
362:
360:
357:
356:
353:
350:
347:
337:
335:
332:
331:
327:
324:
321:
318:
315:
314:
301:
299:
295:
290:
286:
284:
280:
276:
272:
266:
264:
260:
256:
252:
247:
245:
242:having three
241:
229:
217:
213:
209:
201:
198:(also called
197:
193:
188:
182:
172:
169:
162:
157:
153:
147:
143:
136:
131:
127:
123:
118:
116:
112:
108:
104:
100:
96:
92:
88:
83:
81:
77:
76:
71:
67:
63:
59:
55:
52:
49:
45:
41:
38:(also called
37:
33:
26:
21:
2824:Cycloalkanes
2768:Cycloheptane
2758:Cyclopentane
2748:Cyclopropane
2737:Cycloalkanes
2736:
2657:
2553:
2545:
2537:
2490:
2482:
2474:
2435:
2409:Pseudocumene
2373:Ethylbenzene
2354:
2346:
2338:
2269:Phenanthrene
2177:hydrocarbons
2052:Cycloheptyne
2042:Cyclopentyne
2032:Cyclopropyne
2024:Cycloalkynes
1941:Cycloheptene
1931:Cyclopentene
1921:Cyclopropene
1913:Cycloalkenes
1800:
1793:
1671:
1664:
1651:hydrocarbons
1632:Spiroalkanes
1462:Cycloheptane
1452:Cyclopentane
1442:Cyclopropane
1434:Cycloalkanes
1433:
1301:
1294:
1281:hydrocarbons
1270:Hydrocarbons
1186:Cycloalkanes
1179:
1163:
1136:
1130:
1113:
1107:
1098:
1075:
1069:
1065:
1054:
1035:
1029:
1004:
1000:
956:
949:
938:. Retrieved
934:
925:
914:. Retrieved
910:
877:
869:
834:
819:
801:
794:
775:
768:
736:
721:
681:
678:
663:
639:
625:
619:
614:cyclopentane
611:
604:
600:cyclopropane
597:
576:
574:
540:
437:Cycloheptane
385:Cyclopentane
334:Cyclopropane
293:
291:
287:
274:
267:
262:
258:
253:alkanes and
248:
216:cyclopropane
205:
199:
175:Nomenclature
167:
160:
155:
151:
145:
141:
134:
125:
119:
107:cycloheptane
99:cyclopentane
91:cyclopropane
86:
84:
74:
73:
54:hydrocarbons
39:
36:cycloalkanes
35:
29:
2783:Cyclodecane
2778:Cyclononane
2773:Cyclooctane
2763:Cyclohexane
2753:Cyclobutane
2457:C4-Benzenes
2414:Hemellitene
2387:C3-Benzenes
2321:C2-Benzenes
2284:Corannulene
2203:Naphthalene
2067:Cyclodecyne
2062:Cyclononyne
2057:Cyclooctyne
2047:Cyclohexyne
2037:Cyclobutyne
1956:Cyclodecene
1951:Cyclononene
1946:Cyclooctene
1936:Cyclohexene
1926:Cyclobutene
1646:Unsaturated
1477:Cyclodecane
1472:Cyclononane
1467:Cyclooctane
1457:Cyclohexane
1447:Cyclobutane
1109:Tetrahedron
931:"Blue Book"
884:Cycloalkane
855:Cycloalkene
765:Preparation
743:ring strain
728:adipic acid
688:cyclohexane
622:cyclohexane
606:Cyclobutane
559:ring strain
515:Cyclodecane
489:Cyclononane
463:Cyclooctane
411:Cyclohexane
359:Cyclobutane
275:common name
126:cycloalkane
111:cyclooctane
109:), medium (
103:cyclohexane
97:), common (
95:cyclobutane
66:side chains
44:naphthalene
25:cyclobutane
2516:Prehnitene
2404:Mesitylene
2259:Circulenes
2208:Anthracene
2136:Alkatriene
2105:Heptadiene
2095:Pentadiene
2085:Propadiene
2014:Norbornene
1884:Isoheptyne
1874:Isopentyne
1759:Isoheptene
1749:Isopentene
1571:Diamondoid
1566:Adamantane
1541:Norbornane
1405:Isoheptane
1395:Neopentane
1385:Isopentane
1045:0534373674
940:2023-04-01
916:2022-02-20
861:References
626:chair form
580:hybridized
304:Properties
300:industry.
294:naphthenes
196:Norbornane
185:See also:
179:See also:
48:monocyclic
46:) are the
40:naphthenes
2685:Annulynes
2680:Annulenes
2521:Isodurene
2254:Helicenes
2228:Heptacene
2218:Pentacene
2213:Tetracene
2141:Alkadiyne
2120:Decadiene
2115:Nonadiene
2110:Octadiene
2100:Hexadiene
2090:Butadiene
1899:Isodecyne
1894:Isononyne
1889:Isooctyne
1879:Isohexyne
1774:Isodecene
1769:Isononene
1764:Isooctene
1754:Isohexene
1744:Isobutene
1649:aliphatic
1606:Churchane
1601:Basketane
1420:Isodecane
1415:Isononane
1410:Isooctane
1400:Isohexane
1380:Isobutane
1279:aliphatic
1277:Saturated
1001:Chemtexts
753:, but in
692:catalysts
684:oxidation
660:Reactions
551:densities
298:petroleum
279:terpineol
51:saturated
2818:Category
2289:Kekulene
2274:Chrysene
2264:Butalene
2249:Fluorene
2223:Hexacene
2175:Aromatic
2146:Cumulene
1616:Twistane
1611:Pagodane
1591:Prismane
1062:(1968).
1021:94348487
839:See also
319:Formula
251:bicyclic
150:, where
113:through
58:hydrogen
2642:Benzene
2616:Styrene
2493:-Cymene
2485:-Cymene
2477:-Cymene
2466:Cymenes
2357:-Xylene
2349:-Xylene
2341:-Xylene
2330:Xylenes
2311:Toluene
2244:Azulene
1843:Heptyne
1833:Pentyne
1823:Propyne
1788:Alkynes
1713:Heptene
1703:Pentene
1693:Propene
1659:Alkenes
1581:Sterane
1547:Decalin
1535:Housane
1349:Heptane
1339:Pentane
1329:Propane
1319:Methane
1289:Alkanes
747:alkenes
509:0.8534
316:Alkane
261:-" or "
259:bicyclo
238:) - an
228:propane
187:Alkanes
80:alkenes
2511:Durene
2430:Cumene
2279:Pyrene
2195:Acenes
2077:Dienes
1858:Decyne
1853:Nonyne
1848:Octyne
1838:Hexyne
1828:Butyne
1818:Ethyne
1728:Decene
1723:Nonene
1718:Octene
1708:Hexene
1698:Butene
1688:Ethene
1586:Cubane
1364:Decane
1359:Nonane
1354:Octane
1344:Hexane
1334:Butane
1324:Ethane
1151:
1086:
1042:
1019:
972:
549:, and
535:0.871
506:10-11
483:0.834
457:0.811
451:118.4
431:0.778
405:0.751
402:−93.9
379:0.720
244:carbon
240:alkane
212:carbon
208:alkane
105:, and
70:single
62:carbon
34:, the
2673:Other
2658:trans
2635:Other
2574:Other
2530:Other
2423:Other
2366:Other
2237:Other
2161:Enyne
2129:Other
1625:Other
1176:IUPAC
1017:S2CID
1007:(3).
997:(PDF)
874:IUPAC
732:nylon
710:→ 2 C
675:noice
532:9-10
480:14.6
425:80.7
399:49.2
373:12.5
351:−128
263:spiro
255:spiro
2554:tert
2186:PAHs
1149:ISBN
1084:ISBN
1040:ISBN
970:ISBN
820:The
795:The
741:and
529:201
503:169
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