807:
substituents. The total number of organic substituents in organic chemistry is estimated at 3.1 million, creating a total of 6.7×10 molecules. An infinite number of substituents can be obtained simply by increasing carbon chain length. For instance, the substituents methyl
786:
in a set of 3,043,941 molecules. Fifty substituents can be considered common as they are found in more than 1% of this set, and 438 are found in more than 0.1%. 64% of the substituents are found in only one molecule. The top 5 most common are the
475:
According to the above rules, a carbon atom in a molecule, considered as a substituent, has the following names depending on the number of hydrogens bound to it, and the type of bonds formed with the remainder of the molecule:
133:, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between
1178:
Ertl, P. (2003). "Cheminformatics
Analysis of Organic Substituents: Identification of the Most Common Substituents, Calculation of Substituent Properties, and Automatic Identification of Drug-like Bioisosteric Groups".
180:
is used as a reference of comparison. Using methane as a reference, for each hydrogen atom that is replaced or "substituted" by something else, the molecule can be said to be more highly substituted. For example:
1067:
En désignant, par conséquent, les éléments combustibles par R, sans tenir comptes des proportions atomiques de carbone et d'hydrogène, on peut exprimer d'une manière générale: Par R. — Les hydrogènes carbonés.
654:
640:
408:) and adding the appropriate suffix. This is "recommended only for saturated acyclic and monocyclic hydrocarbon substituent groups and for the mononuclear parent
626:
668:
584:
612:
1165:
X indica tutto ciò che vi è nella molecola, oltre l'idrogeno metallico … " ( … X stands for all that is in the molecule, apart from metallic hydrogen … ).
388:
For many common compounds the substituent is linked at one end (the 1 position) and historically not numbered in the name. The IUPAC 2013 Rules however
1012:. Favre, Henri A.,, Powell, Warren H., 1934–, International Union of Pure and Applied Chemistry. Cambridge, UK: Royal Society of Chemistry. 2013.
1232:
276:
was extracted. Several reforms of chemical nomenclature eventually generalized the use of the suffix to other organic substituents.
1241:
78:, are used almost interchangeably to describe those branches from the parent structure, though certain distinctions are made in
328:
is encountered sporadically, and appears to be a variant spelling of "-ylidene"; it is not mentioned in the IUPAC guidelines.
886:
440:-yl" typically denotes the same carbon chain lacking these groups but modified by attachment to some other parent molecule.
1017:
443:
The more general method omits only the terminal "e" of the substituent name, but requires explicit numbering of each
1092:
202:
predicts that the major reaction product is the alkene with the more highly substituted (more stable) double bond.
727:, which may replace any portion of the formula as the author finds convenient. The first to use this symbol was
1562:
728:
1225:
20:
1073:, without considering the atomic proportions of carbon and hydrogen, one can express in a general way: By
1557:
1041:
279:
The use of the suffix is determined by the number of hydrogen atoms that the substituent replaces on a
1218:
754:
study identified 849,574 unique substituents up to 12 non-hydrogen atoms large and containing only
331:
For multiple bonds of the same type, which link the substituent to the parent group, the infixes
1061:(Summary of organic chemistry), vol. 1 (Paris, France: Fortin et Masson, 1844), page 29. From
241:
1160:
1148:
904:"PAC, 1996, 68, 2287. Glossary of basic terms in polymer science (IUPAC Recommendations 1996)"
1567:
1062:
876:
185:
1504:
1115:
962:
686:
397:
150:
8:
1535:
1376:
850:
717:
421:
223:
169:
1119:
1322:
1151:(Sketch of a course of chemical philosophy, offered at the Royal University of Genoa),
1035:
692:
232:
41:
467:" (when used to mean "polyvinyl") represent only a portion of the full chemical name.
1196:
1080:
1023:
1013:
882:
219:
199:
173:
49:
29:
1188:
1123:
915:
903:
829:
570:
142:
138:
110:
62:
1366:
1010:
Nomenclature of
Organic Chemistry. IUPAC Recommendations and Preferred Names 2013
751:
544:
413:
280:
1106:
Jensen, W. B. (2010). "Why Is "R" Used To
Symbolize Hydrocarbon Substituents?".
723:
154:
87:
1551:
1149:"Sunto di un corso di filosofia chimica, fatto nella R. Universita di Genova"
1027:
598:
363:
146:
74:
1210:
920:
1200:
788:
519:
269:
237:
95:
53:
1083:(2010) "Ask the Historian: Why is R Used for Hydrocarbon Substituents?,"
16:
Atom set which has replaced hydrogen atoms on a hydrocarbon's parent chain
1302:
1282:
969:. Blackwell Scientific Publications; Advanced Chemistry Development, Inc.
967:
A Guide to IUPAC Nomenclature of
Organic Compounds (Recommendations 1993)
700:
448:
314:
301:
130:
126:
114:
1308:
902:
Jenkins, A. D.; Kratochvíl, P.; Stepto, R. F. T.; Suter, U. W. (1996).
775:
192:
functional group which has the greater number of hydrogen atoms (fewer
99:
68:
1192:
1127:
1362:
464:
262:
249:
19:
This article is about the term in chemistry. For other meanings, see
1430:
1420:
1407:
1346:
1312:
804:
796:
779:
763:
759:
83:
45:
412:
of silicon, germanium, tin, lead, and boron". Thus, if there is a
980:
800:
783:
739:
738:
is often used to denote electronegative substituents such as the
495:
409:
177:
91:
79:
1525:
1462:
1458:
1445:
1434:
1386:
1333:
1318:
1292:
1272:
1262:
1249:
792:
771:
767:
755:
696:
455:
is an example of a name by this method, and is synonymous with
405:
393:
283:(and also, usually, on the substituent). According to the 1993
189:
134:
188:
predicts that the hydrogen atom is added to the carbon of the
168:
are frequently used to describe or compare molecules that are
1491:
1479:
1454:
1396:
1356:
1352:
963:"R-2.5 Substituent Prefix Names Derived from Parent Hydrides"
362:
For multiple bonds of different types, multiple suffixes are
284:
256:
212:
193:
987:, of which 14 have synonyms where the suffix is replaced by
901:
447:
prefix, even at position 1 (except for -ylidyne, which as a
1521:
1497:
1485:
1426:
1416:
1392:
1382:
1298:
1288:
1278:
1268:
1258:
1069:" (Consequently, by designating combustible components by
704:
37:
1372:
1342:
1144:
to denote univalent electronegative groups appeared in:
40:
that replaces (one or more) atoms, thereby becoming a
384:
The parent compound name can be altered in two ways:
943:
This name came through a Greek language error: ὕλη (
230:) or chemically bonded parts of molecules (called
157:result from the volume occupied by a substituent.
711:(or R, R, etc.) It is a generic placeholder, the
1549:
400:. The substituent name is modified by stripping
268:, 'wood', 'forest'), which became shortened to "
930:as neither oligomeric nor polymeric, whereas a
451:must terminate the substituent carbon chain).
1240:
1226:
313:means that three hydrogens are replaced by a
1181:Journal of Chemical Information and Modeling
236:). It can be traced back to the old name of
745:
300:means that two hydrogens are replaced by a
137:. Substituents can be a combination of the
1233:
1219:
874:
919:
525:one single bond to a non-hydrogen atom
470:
1550:
1105:
463:Note that some popular terms such as "
145:. Such effects are also described as
1214:
960:
660:two single bonds and one double bond
1177:
632:one triple bond and one single bond
604:one single bond and one double bond
432:-yl alcohol"), or an alkane called "
294:means that one hydrogen is replaced.
983:database lists 740,110 results for
601:or methanylylidene or methylylidene
13:
947:) means "wood" ("forest"), ξυλο- (
226:, either separate species (called
94:, side chains are attached to the
14:
1579:
1531:
695:, an organic substituent such as
934:must be oligomeric or polymeric.
272:" in compound names, from which
1171:
1134:
951:-) means "wood" (the substance)
547:or methanylidene or methylidene
317:between parent and substituent.
304:between parent and substituent.
206:
1099:
1048:
1002:
973:
954:
937:
895:
868:
843:
86:, side chains extend from the
1:
1505:ordinary Greek/Latin prefixes
1108:Journal of Chemical Education
1085:Journal of Chemical Education
878:Organic Chemistry Demystified
836:
381:(two single and one double).
377:(one single and one triple),
373:(one single and one double),
21:Substitution (disambiguation)
1147:Stanislao Cannizzaro (1858)
1140:The first use of the letter
1091:: 360–361. Available at:
991:. Another 4 results contain
832:are a subset of substituents
459:from the previous guideline.
263:
250:
7:
851:"Definition of SUBSTITUENT"
823:
680:
396:for most substituents in a
10:
1584:
1059:Précis de chimie organique
908:Pure and Applied Chemistry
684:
573:or methanediyl or methdiyl
257:
245:
18:
1514:
1472:
1444:
1406:
1332:
1248:
1242:Organic chemistry affixes
1093:University of Cincinnati.
729:Charles Frédéric Gerhardt
746:Statistical distribution
655:methanediylylidene group
117:replacing one hydrogen;
921:10.1351/pac199668122287
855:www.merriam-webster.com
176:. In this terminology,
44:in the resultant (new)
1155:(The New Experiment),
1040:: CS1 maint: others (
641:methanediylidene group
351:(three single bonds),
1563:Chemical nomenclature
926:This distinguishes a
685:Further information:
627:methanylylidyne group
355:(four single bonds),
36:is one or a group of
1473:Counting axial atoms
687:Pseudoelement symbol
669:methanetetrayl group
471:Methane substituents
398:preferred IUPAC name
392:require an explicit
359:(two double bonds).
347:(two single bonds),
240:, "methylene" (from
151:electron withdrawing
109:is used when naming
1159: : 321–366.
1120:2010JChEd..87..360J
875:D.R. Bloch (2006).
618:three single bonds
585:methanylidyne group
1503:(and the rest are
1057:Charles Gerhardt,
707:can be written as
693:structural formula
674:four single bonds
657:or methdiylylidene
613:methanetriyl group
343:, etc., are used:
186:Markovnikov's rule
1558:Organic chemistry
1545:
1544:
1193:10.1021/ci0255782
1128:10.1021/ed800139p
1081:William B. Jensen
914:(12): 2287–2311.
888:978-0-07-145920-4
830:Functional groups
678:
677:
646:two double bonds
576:two single bonds
287:recommendations:
222:to form names of
220:organic chemistry
174:chemical reaction
166:least-substituted
111:organic compounds
50:organic chemistry
30:organic chemistry
1575:
1235:
1228:
1221:
1212:
1211:
1205:
1204:
1175:
1169:
1153:Il Nouvo Cimento
1138:
1132:
1131:
1103:
1097:
1077:— hydrocarbons.)
1052:
1046:
1045:
1039:
1031:
1006:
1000:
995:without listing
977:
971:
970:
958:
952:
941:
935:
925:
923:
899:
893:
892:
872:
866:
865:
863:
861:
847:
812:) and pentyl (-C
643:or methdiylidene
629:or methylylidyne
590:one triple bond
571:methylene bridge
566:
565:
564:
550:one double bond
541:
540:
539:
516:
515:
514:
492:
491:
490:
479:
478:
266:
260:
259:
253:
247:
162:most-substituted
143:mesomeric effect
139:inductive effect
63:functional group
1583:
1582:
1578:
1577:
1576:
1574:
1573:
1572:
1548:
1547:
1546:
1541:
1510:
1468:
1440:
1402:
1367:carboxylic acid
1328:
1244:
1239:
1209:
1208:
1176:
1172:
1139:
1135:
1104:
1100:
1053:
1049:
1033:
1032:
1020:
1008:
1007:
1003:
978:
974:
961:IUPAC (1997) .
959:
955:
942:
938:
900:
896:
889:
873:
869:
859:
857:
849:
848:
844:
839:
826:
819:
815:
811:
752:cheminformatics
748:
689:
683:
563:
560:
559:
558:
556:
545:methylene group
538:
535:
534:
533:
531:
513:
510:
509:
508:
506:
489:
486:
485:
484:
482:
473:
414:carboxylic acid
281:parent compound
209:
113:that contain a
24:
17:
12:
11:
5:
1581:
1571:
1570:
1565:
1560:
1543:
1542:
1540:
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1469:
1467:
1466:
1451:
1449:
1442:
1441:
1439:
1438:
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1413:
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1404:
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1401:
1400:
1390:
1380:
1370:
1360:
1350:
1339:
1337:
1330:
1329:
1327:
1326:
1316:
1306:
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1286:
1276:
1266:
1255:
1253:
1246:
1245:
1238:
1237:
1230:
1223:
1215:
1207:
1206:
1187:(2): 374–380.
1170:
1168:
1167:
1161:From page 355:
1133:
1114:(4): 360–361.
1098:
1096:
1095:
1078:
1047:
1018:
1001:
972:
953:
936:
894:
887:
867:
841:
840:
838:
835:
834:
833:
825:
822:
817:
813:
809:
747:
744:
691:In a chemical
682:
679:
676:
675:
672:
671:or methtetrayl
666:
662:
661:
658:
652:
648:
647:
644:
638:
634:
633:
630:
624:
620:
619:
616:
610:
606:
605:
602:
596:
592:
591:
588:
587:or methylidyne
582:
578:
577:
574:
568:
561:
552:
551:
548:
542:
536:
527:
526:
523:
517:
511:
502:
501:
498:
493:
487:
472:
469:
461:
460:
441:
420:-ic acid", an
319:
318:
305:
295:
208:
205:
204:
203:
200:Zaitsev's rule
197:
196:substituents).
155:steric effects
125:are used with
90:structure. In
82:chemistry. In
15:
9:
6:
4:
3:
2:
1580:
1569:
1566:
1564:
1561:
1559:
1556:
1555:
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1527:
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1478:
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1471:
1464:
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1443:
1436:
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1428:
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1422:
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1415:
1414:
1412:
1409:
1405:
1398:
1394:
1391:
1388:
1384:
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1378:
1374:
1371:
1368:
1364:
1361:
1358:
1354:
1351:
1348:
1344:
1341:
1340:
1338:
1335:
1331:
1324:
1320:
1317:
1314:
1310:
1307:
1304:
1301:(nonaromatic
1300:
1297:
1294:
1290:
1287:
1284:
1281:(unsaturated
1280:
1277:
1274:
1270:
1267:
1264:
1260:
1257:
1256:
1254:
1251:
1247:
1243:
1236:
1231:
1229:
1224:
1222:
1217:
1216:
1213:
1202:
1198:
1194:
1190:
1186:
1182:
1174:
1166:
1162:
1158:
1154:
1150:
1146:
1145:
1143:
1137:
1129:
1125:
1121:
1117:
1113:
1109:
1102:
1094:
1090:
1086:
1082:
1079:
1076:
1072:
1068:
1064:
1060:
1056:
1055:
1051:
1043:
1037:
1029:
1025:
1021:
1019:9781849733069
1015:
1011:
1005:
999:as a synonym.
998:
994:
990:
986:
982:
976:
968:
964:
957:
950:
946:
940:
933:
932:pendant chain
929:
928:pendant group
922:
917:
913:
909:
905:
898:
890:
884:
880:
879:
871:
856:
852:
846:
842:
831:
828:
827:
821:
806:
802:
798:
794:
790:
785:
781:
777:
773:
769:
765:
761:
757:
753:
743:
741:
737:
732:
730:
726:
725:
720:
719:
715:derived from
714:
710:
706:
702:
698:
694:
688:
673:
670:
667:
664:
663:
659:
656:
653:
650:
649:
645:
642:
639:
636:
635:
631:
628:
625:
622:
621:
617:
614:
611:
608:
607:
603:
600:
599:methine group
597:
594:
593:
589:
586:
583:
580:
579:
575:
572:
569:
554:
553:
549:
546:
543:
529:
528:
524:
521:
518:
504:
503:
499:
497:
494:
481:
480:
477:
468:
466:
458:
454:
450:
446:
442:
439:
436:-ane", then "
435:
431:
427:
423:
419:
415:
411:
407:
403:
399:
395:
391:
387:
386:
385:
382:
380:
376:
372:
369:
365:
360:
358:
354:
350:
346:
342:
338:
334:
329:
327:
326:
316:
312:
309:
306:
303:
299:
296:
293:
290:
289:
288:
286:
282:
277:
275:
271:
267:
265:
255:, 'wine' and
254:
252:
243:
242:Ancient Greek
239:
235:
234:
229:
228:free radicals
225:
221:
217:
214:
201:
198:
195:
191:
187:
184:
183:
182:
179:
175:
171:
167:
163:
158:
156:
153:. Additional
152:
148:
147:electron-rich
144:
140:
136:
132:
128:
124:
120:
116:
112:
108:
103:
101:
98:atoms of the
97:
93:
89:
85:
81:
77:
76:
75:pendant group
71:
70:
66:, as well as
65:
64:
59:
55:
51:
47:
43:
39:
35:
31:
26:
22:
1568:Substituents
1184:
1180:
1173:
1164:
1156:
1152:
1141:
1136:
1111:
1107:
1101:
1088:
1084:
1074:
1070:
1066:
1058:
1050:
1009:
1004:
996:
992:
988:
984:
975:
966:
956:
948:
944:
939:
931:
927:
911:
907:
897:
877:
870:
858:. Retrieved
854:
845:
749:
735:
733:
722:
716:
712:
708:
690:
615:or methtriyl
520:methyl group
474:
462:
456:
452:
444:
437:
433:
429:
428:-anol" (or "
425:
417:
401:
389:
383:
379:-diylylidene
378:
374:
370:
367:
364:concatenated
361:
356:
352:
348:
344:
340:
336:
332:
330:
324:
322:
320:
310:
307:
297:
291:
278:
273:
261:
248:
231:
227:
215:
210:
207:Nomenclature
165:
161:
160:The phrases
159:
131:triple bonds
127:double bonds
122:
118:
106:
104:
96:alpha carbon
73:
67:
61:
57:
56:, the terms
54:biochemistry
33:
27:
25:
1303:hydrocarbon
1283:hydrocarbon
734:The symbol
522:or methanyl
453:Pentan-1-yl
449:triple bond
321:The suffix
315:triple bond
302:double bond
218:is used in
115:single bond
105:The suffix
102:backbone.)
58:substituent
34:substituent
1552:Categories
837:References
782:, and the
776:phosphorus
375:-ylylidyne
357:-diylidene
100:amino acid
69:side chain
1461:replaces
1433:replaces
1363:-oic acid
1036:cite book
1028:865143943
731:in 1844.
665:>C<
500:no bonds
371:ylylidene
1421:alkaloid
1408:Nitrogen
1347:aldehyde
1313:aromatic
1201:12653499
1063:page 29:
997:-ylidene
993:-ylidine
989:-ylidine
985:-ylidene
824:See also
805:hydroxyl
797:chlorine
784:halogens
780:selenium
764:nitrogen
760:hydrogen
681:Notation
424:ending "
416:called "
410:hydrides
353:-tetrayl
298:-ylidene
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1116:Bibcode
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1199:
1026:
1016:
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1197:PMID
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402:-ane
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1500:(4)
1494:(3)
1488:(2)
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637:=C=
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28:In
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1038:}}
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912:68
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1534:(
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1429:(
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864:.
816:H
814:5
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713:R
709:R
567:−
562:2
555:−
537:2
530:=
512:3
505:−
488:4
438:X
434:X
430:X
426:X
418:X
368:-
308:-
23:.
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