2517:
38:
3746:
2499:
3710:
2508:
3734:
3722:
1264:
J. Dumas and E. Péligot (1835) "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent" (Memoir on spirit of wood and on the various ethereal compounds that derive therefrom),
538:, the source of natural gas, arises via a demethylation reaction. Together with ubiquitin and phosphorylation, methylation is a major biochemical process for modifying protein function. The field of
2281:
945:
Poad, Berwyck L. J.; Reed, Nicholas D.; Hansen, Christopher S.; Trevitt, Adam J.; Blanksby, Stephen J.; Mackay, Emily G.; Sherburn, Michael S.; Chan, Bun; Radom, Leo (2016).
1035:
Demarteau, Jérémy; Debuigne, Antoine; Detrembleur, Christophe (2019). "Organocobalt
Complexes as Sources of Carbon-Centered Radicals for Organic and Polymer Chemistries".
3530:
3450:
3266:
3201:
3141:
3069:
2975:
2869:
2739:
2290:
2274:
770:) "wood, patch of trees" with the intention of highlighting its origins, "alcohol made from wood (substance)". The term "methyl" was derived in about 1840 by
1322:
2267:
1226:
1195:
924:
G. Barney
Ellison , P. C. Engelking , W. C. Lineberger (1978), "An experimental determination of the geometry and electron affinity of methyl radical CH
2241:
853:"Webb telescope just found something unprecedented in the Orion Nebula - Astronomers are excited about the detection of a special molecule in space"
2246:
785:
355:; and though the model may be useful for description and analysis, it is only a useful fiction. Such reagents are generally prepared from the
862:
723:. In condensed phases, neighbour molecules also contribute to the potential. Methyl group rotation can be experimentally studied using
3653:
3553:
835:
1279:
Nous donnerons le nom de mĂ©thylĂšne (1) Ă un radical ⊠(1) ΌΔΞÏ
, vin, et Ï
λη, bois; c'est-à -dire vin ou liqueur spiritueuse du bois.
1077:
Thauer, R. K., "Biochemistry of
Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, volume 144, pages 2377â2406.
439:. Methyl groups can be quite unreactive. For example, in organic compounds, the methyl group resists attack by even the strongest
3678:
1315:
724:
3603:
2145:
1178:
M. Rossberg et al. âChlorinated
Hydrocarbonsâ in Ullmannâs Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.
602:
bond is decreased, and the reactivity of the methyl group increases. One manifestation of this enhanced reactivity is the
3638:
1281:(We will give the name "methylene" (1) to a radical ⊠(1) methy, wine, and hulÄ, wood; that is, wine or spirit of wood.)
1255:
Press,W: Single-particle rotation in molecular crystals (Springer tracts in modern physics 92), Springer: Berlin (1981).
2834:
1239:
Heinz G. Floss, Sungsook Lee "Chiral methyl groups: small is beautiful" Acc. Chem. Res., 1993, volume 26, pp 116â122.
3776:
1718:
1308:
744:
3593:
3588:
3401:
2769:
903:
3633:
3059:
2829:
2789:
1755:
329:
1202:
296:) exists only in rarefied gas phase or under exotic conditions. It can be produced by electrical discharge in
2990:
2965:
2955:
3713:
2228:
3568:
3361:
2689:
2630:
2538:
2533:
2443:
2320:
2315:
2128:
321:
2694:
2365:
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3623:
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3236:
2995:
2854:
2839:
2809:
2401:
2235:
2123:
2925:
2905:
2578:
852:
455:
of a methyl group occurs widely in nature and industry. The oxidation products derived from methyl are
2950:
752:
37:
3684:
3668:
3293:
2664:
2635:
2516:
2340:
2204:
1649:
305:
2588:
3628:
3608:
3421:
3111:
2945:
2599:
2463:
2438:
2406:
2325:
1510:
947:"Preparation of an ion with the highest calculated proton affinity: ortho-diethynylbenzene dianion"
736:
456:
396:
157:
2615:
762:
113:. It is a very stable group in most molecules. While the methyl group is usually part of a larger
3726:
3648:
3618:
3563:
3440:
3416:
3161:
2915:
2849:
2714:
2674:
2558:
2525:
2488:
2448:
2427:
2370:
2345:
1060:
774:
from "methylene", and was then applied to describe "methyl alcohol" (which since 1892 is called "
273:
176:, the radical seven and the cation six. All three forms are highly reactive and rarely observed.
2709:
2620:
3673:
3256:
3156:
3126:
3044:
2784:
2669:
2625:
2573:
2380:
2375:
2307:
2194:
2164:
1922:
1544:
1220:
1161:
1120:
1052:
1017:
978:
831:
571:
518:
Demethylation (the transfer of the methyl group to another compound) is a common process, and
412:
340:
110:
52:
2804:
3750:
3738:
3658:
3558:
3488:
3463:
3411:
2844:
2719:
2684:
2605:
2593:
2553:
2458:
2391:
1899:
1393:
1331:
1274:
1240:
1179:
1151:
1110:
1100:
1089:"The ribosome: A hot spot for the identification of new types of protein methyltransferases"
1044:
1009:
968:
958:
929:
895:
890:
550:
Certain methyl groups can be deprotonated. For example, the acidity of the methyl groups in
523:
173:
98:
94:
792:(or alkyl) molecule, using the prefix "meth-" to indicate the presence of a single carbon.
3346:
3321:
3020:
2859:
2799:
2779:
2699:
2583:
2483:
2468:
2453:
2360:
2350:
2118:
1877:
1872:
1855:
1838:
1639:
1388:
1139:
676:
650:
614:
531:
424:
522:
that undergo this reaction are called methylating agents. Common methylating agents are
3583:
3548:
3331:
3221:
3186:
3171:
3106:
3101:
3000:
2900:
2819:
2794:
2759:
2704:
2679:
2548:
2396:
2189:
2184:
2060:
2055:
2050:
1843:
1810:
1594:
1576:
1566:
1115:
1088:
973:
946:
771:
740:
720:
603:
535:
501:
474:
390:
336:
223:
cation, and this simplification is used pervasively in organic chemistry. For example,
211:, but is otherwise not encountered. Some compounds are considered to be sources of the
3765:
3613:
3468:
3351:
3326:
3307:
3251:
3131:
3089:
3084:
2824:
2814:
2774:
2649:
2543:
2498:
2473:
2355:
2335:
2209:
2157:
2088:
1974:
1964:
1959:
1949:
1944:
1894:
1889:
1805:
1800:
1790:
1644:
1599:
1561:
1549:
1520:
1398:
1064:
885:
748:
527:
356:
254:
72:
2259:
3689:
3543:
3396:
3336:
3316:
3288:
3216:
3096:
3079:
3034:
2985:
2890:
2610:
2563:
2411:
2140:
2027:
2022:
1999:
1750:
1589:
1515:
1452:
1447:
1425:
1381:
1366:
654:
606:
575:
493:
481:
467:
378:
1183:
928:" Journal of the American Chemical Society, volume 100, issue 8, pages 2556â2558.
3663:
3573:
3538:
3505:
3431:
3406:
3246:
3151:
3121:
3005:
2920:
2910:
2640:
2568:
2199:
2152:
2113:
1994:
1882:
1867:
1862:
1850:
1415:
1410:
1376:
1371:
1361:
1339:
1048:
806:
638:
513:
436:
420:
266:
261:
are viewed as the equivalent of the methyl cation because they readily undergo S
224:
106:
28:
3578:
3520:
3483:
3458:
3356:
3166:
3029:
2108:
2099:
1979:
1934:
1830:
1795:
1785:
1725:
1661:
1584:
1532:
579:
539:
313:
1165:
1105:
899:
705:) that restricts the free motion of the three protons. For the model case of
17:
3510:
3375:
3211:
3015:
2895:
2749:
2724:
2075:
1989:
1954:
1939:
1927:
1770:
1745:
1554:
626:
567:
452:
317:
309:
208:
190:
1124:
1056:
1021:
982:
886:"Formation of the Methyl Cation by Photochemistry in a Protoplanetary Disk"
227:
of methanol gives an electrophilic methylating reagent that reacts by the S
3478:
3390:
3191:
3054:
3039:
3010:
2879:
2654:
2478:
2422:
2416:
2385:
2330:
2298:
2083:
2037:
2004:
1700:
1606:
1480:
1435:
1420:
857:
775:
637:. Methods exist to produce optically pure methyl compounds, e.g., chiral
591:
258:
114:
76:
1244:
933:
3643:
3473:
3426:
3385:
3341:
3283:
3278:
3241:
3231:
3226:
3181:
3176:
3116:
3049:
2940:
2935:
2885:
2764:
2754:
2507:
2045:
1969:
1820:
1815:
1780:
1765:
1760:
1730:
1713:
1537:
1464:
1430:
1156:
963:
666:
630:
610:
595:
551:
519:
489:
64:
1013:
675:
axis. This is a free rotation only in the simplest cases like gaseous
411:. It exists in dilute gases, but in more concentrated form it readily
3694:
3515:
3497:
2960:
2930:
2432:
2133:
2065:
1909:
1618:
1611:
1505:
1486:
1475:
1459:
1405:
801:
789:
706:
634:
497:
416:
297:
141:
68:
1300:
2729:
2659:
2014:
1984:
1917:
1775:
1740:
1735:
1708:
1656:
1623:
1527:
1351:
125:
60:
36:
1442:
828:
Advanced organic chemistry: reactions, mechanisms, and structure
440:
301:
117:, bonded to the rest of the molecule by a single covalent bond (
2263:
1304:
743:, after determining methanol's chemical structure, introduced "
124:), it can be found on its own in any of three forms: methanide
41:
Different ways of representing a methyl group (highlighted in
1290:
Note that the correct Greek word for the substance "wood" is
566:) is about 10 times more acidic than methane. The resulting
542:
focuses on the influence of methylation on gene expression.
435:
The reactivity of a methyl group depends on the adjacent
996:
Toraya, Tetsuo (2003). "Radical
Catalysis in Coenzyme B
625:
In the special case where one hydrogen is replaced by
419:. It is routinely produced by various enzymes of the
3529:
3449:
3374:
3265:
3200:
3140:
3068:
2974:
2868:
2738:
2524:
2306:
2297:
2177:
2097:
2074:
2036:
2013:
1908:
1829:
1699:
1676:
1632:
1575:
1498:
1473:
1338:
1000:-Dependent Isomerization (Eliminating) Reactions".
1140:"DNA methylation patterns and epigenetic memory"
686:. In most molecules, the remainder R breaks the
649:). Through the use of chiral methyl groups, the
335:In discussing mechanisms of organic reactions,
496:. Ultimately oxidation of methyl groups gives
2275:
1316:
484:often converts a methyl group to a carboxyl (
8:
884:Berne, Olivier; et al. (26 June 2023).
570:are key intermediates in many reactions in
2303:
2282:
2268:
2260:
1696:
1495:
1323:
1309:
1301:
34:Chemical group (âCHâ) derived from methane
1155:
1114:
1104:
972:
962:
715:
711:
681:
644:
561:
557:
461:
369:
365:
245:
241:
237:
120:
89:
86:(whereas normal methane has the formula
82:
818:
786:IUPAC nomenclature of organic chemistry
272:The methyl cation has been detected in
1225:: CS1 maint: archived copy as title (
1218:
308:is determined to be about 252.2 ± 3.3
671:A methyl group may rotate around the
7:
657:transformations have been analyzed.
633:(T), the methyl substituent becomes
343:are often considered to be salts of
719:, this is discussed under the name
3654:Nexus for Exoplanet System Science
25:
3554:Atomic and molecular astrophysics
2291:Molecules detected in outer space
906:from the original on 27 June 2023
865:from the original on 27 June 2023
180:Methyl cation, anion, and radical
3744:
3732:
3720:
3709:
3708:
2515:
2506:
2497:
1267:Annales de chimie et de physique
488:) group, e.g. the conversion of
3679:Polycyclic aromatic hydrocarbon
1093:Journal of Biological Chemistry
851:Sauers, Elisha (27 June 2023).
725:quasielastic neutron scattering
598:positions, the strength of the
300:at low pressure (less than one
79:atoms, having chemical formula
1:
3604:Extraterrestrial liquid water
1184:10.1002/14356007.a06_233.pub2
697:axis and creates a potential
629:(D) and another hydrogen by
2835:Protonated hydrogen cyanide
1138:Bird, Adrian (2002-01-01).
1049:10.1021/acs.chemrev.8b00715
3793:
1087:Clarke, Steven G. (2018).
761:
751:
664:
582:are produced in this way.
511:
388:
332:are known to be stronger.
188:
26:
3703:
3594:Earliest known life forms
3589:Diffuse interstellar band
3060:Protonated cyanoacetylene
2830:Protonated carbon dioxide
2790:Hydromagnesium isocyanide
2495:
2218:
830:. John Wiley & Sons.
641:(deuterotritoacetic acid
504:, as seen in combustion.
330:diethynylbenzene dianions
3639:Ironâsulfur world theory
3634:Photodissociation region
3337:Methyl-cyano-diacetylene
1106:10.1074/jbc.AW118.003235
900:10.1038/s41586-023-06307
27:Not to be confused with
3714:Category:Astrochemistry
3304:, fullerene, buckyball)
2991:Cyanobutadiynyl radical
2966:Silicon-carbide cluster
2956:Protonated formaldehyde
2229:chemical classification
1144:Genes & Development
609:of the methyl group in
172:). The anion has eight
3727:Outer space portal
3569:Circumstellar envelope
2534:Aluminium(I) hydroxide
2444:Phosphorus mononitride
2321:Aluminium monofluoride
2316:Aluminium monochloride
586:Free radical reactions
322:lithium monoxide anion
195:The methylium cation (
48:
3624:Interplanetary medium
3599:Extraterrestrial life
3237:Octatetraynyl radical
2855:Tricarbon monosulfide
2402:Magnesium monohydride
2236:chemical nomenclature
826:March, Jerry (1992).
284:The methanide anion (
109:group occurs in many
97:, the group is often
40:
3751:Chemistry portal
3739:Astronomy portal
3685:RNA world hypothesis
3669:PAH world hypothesis
3362:Heptatrienyl radical
3294:Buckminsterfullerene
3182:Methylcyanoacetylene
2690:Silicon carbonitride
2665:Methylidynephosphane
2631:Magnesium isocyanide
2539:Aluminium isocyanide
2341:Carbon monophosphide
306:enthalpy of reaction
265:2 reactions by weak
3629:Interstellar medium
3609:Forbidden mechanism
3422:Hydrogen isocyanide
3112:Hexatriynyl radical
2695:c-Silicon dicarbide
2600:Hydrogen isocyanide
2464:Silicon monosulfide
2439:Phosphorus monoxide
2407:Methylidyne radical
2366:Fluoromethylidynium
2326:Aluminium(II) oxide
1692:not C, H or O)
1273: : 5-74; from
1245:10.1021/ar00027a007
1099:(27): 10438â10446.
934:10.1021/ja00476a054
737:Jean-Baptiste Dumas
457:hydroxymethyl group
316:. It is a powerful
3649:Molecules in stars
3619:Intergalactic dust
3564:Circumstellar dust
3506:Naphthalene cation
3441:Trihydrogen cation
3417:Hydrogen deuteride
3342:Methyltriacetylene
3177:Hexapentaenylidene
2996:E-Cyanomethanimine
2916:Cyclopropenylidene
2850:Tricarbon monoxide
2840:Silicon tricarbide
2810:Methylene amidogen
2800:Isothiocyanic acid
2715:Thioxoethenylidene
2675:Trihydrogen cation
2489:Titanium(II) oxide
2449:Potassium chloride
2428:Sulfur mononitride
2371:Helium hydride ion
2346:Carbon monosulfide
2134:Hypervalent iodine
1157:10.1101/gad.947102
964:10.1039/C6SC01726F
653:course of several
274:interstellar space
49:
3777:Functional groups
3759:
3758:
3674:Pseudo-panspermia
3370:
3369:
3317:Cyanodecapentayne
3257:N-Methylformamide
3232:Methyldiacetylene
3157:Aminoacetonitrile
3127:Methyl isocyanate
3045:Methyl isocyanide
2926:Isocyanoacetylene
2906:Cyanoformaldehyde
2785:Hydrogen peroxide
2670:Potassium cyanide
2626:Magnesium cyanide
2579:Disilicon carbide
2574:Dicarbon monoxide
2381:Hydrogen fluoride
2376:Hydrogen chloride
2257:
2256:
2195:Sulfenyl chloride
2173:
2172:
1672:
1671:
1491:(only C, H and O)
1332:Functional groups
1043:(12): 6906â6955.
1014:10.1021/cr020428b
572:organic synthesis
341:Grignard reagents
174:valence electrons
111:organic compounds
67:, containing one
53:organic chemistry
16:(Redirected from
3784:
3749:
3748:
3747:
3737:
3736:
3735:
3725:
3724:
3723:
3712:
3711:
3659:Organic compound
3559:Chemical formula
3464:Dihydroxyacetone
3412:Hydrogen cyanide
3097:Cyanodiacetylene
2951:Propadienylidene
2845:Thioformaldehyde
2720:Titanium dioxide
2685:Sodium hydroxide
2606:Hydrogen sulfide
2594:Hydrogen cyanide
2554:Carbonyl sulfide
2519:
2510:
2501:
2459:Silicon monoxide
2392:Hydroxyl radical
2304:
2284:
2277:
2270:
2261:
2224:
2129:Trifluoromethoxy
1697:
1693:
1496:
1492:
1345:
1325:
1318:
1311:
1302:
1295:
1288:
1282:
1262:
1256:
1253:
1247:
1237:
1231:
1230:
1224:
1216:
1214:
1213:
1207:
1201:. Archived from
1200:
1192:
1186:
1176:
1170:
1169:
1159:
1135:
1129:
1128:
1118:
1108:
1084:
1078:
1075:
1069:
1068:
1037:Chemical Reviews
1032:
1026:
1025:
1008:(6): 2095â2128.
1002:Chemical Reviews
993:
987:
986:
976:
966:
957:(9): 6245â6250.
951:Chemical Science
942:
936:
922:
916:
915:
913:
911:
881:
875:
874:
872:
870:
848:
842:
841:
823:
765:
755:
735:French chemists
718:
696:
693:symmetry of the
685:
674:
648:
601:
565:
524:dimethyl sulfate
487:
479:
472:
465:
410:
409:
408:
399:has the formula
373:
354:
353:
352:
349:
327:
295:
294:
293:
290:
249:
240:OH + H â [CH
222:
221:
220:
217:
207:) exists in the
206:
205:
204:
201:
171:
170:
169:
155:
154:
153:
150:
139:
138:
137:
134:
123:
92:
85:
46:
21:
3792:
3791:
3787:
3786:
3785:
3783:
3782:
3781:
3762:
3761:
3760:
3755:
3745:
3743:
3733:
3731:
3721:
3719:
3699:
3525:
3501:
3492:
3445:
3435:
3378:
3366:
3347:Propionaldehyde
3322:Ethylene glycol
3311:
3303:
3299:
3270:
3268:
3261:
3217:Cyanohexatriyne
3203:
3196:
3143:
3136:
3071:
3064:
3024:
2977:
2970:
2941:Methoxy radical
2871:
2864:
2860:Thiocyanic acid
2741:
2734:
2644:
2584:Ethynyl radical
2520:
2514:
2513:
2512:
2511:
2505:
2504:
2503:
2502:
2493:
2484:Sulfur monoxide
2469:Sodium chloride
2454:Silicon carbide
2361:Diatomic carbon
2351:Carbon monoxide
2293:
2288:
2258:
2253:
2222:
2214:
2169:
2124:Trichloromethyl
2119:Trifluoromethyl
2093:
2070:
2032:
2009:
1904:
1873:Phosphine oxide
1825:
1691:
1689:
1688:
1686:
1684:
1682:
1680:
1678:
1668:
1628:
1571:
1490:
1489:
1484:
1479:
1469:
1343:
1342:
1334:
1329:
1299:
1298:
1289:
1285:
1263:
1259:
1254:
1250:
1238:
1234:
1217:
1211:
1209:
1205:
1198:
1196:"Archived copy"
1194:
1193:
1189:
1177:
1173:
1137:
1136:
1132:
1086:
1085:
1081:
1076:
1072:
1034:
1033:
1029:
999:
995:
994:
990:
944:
943:
939:
927:
923:
919:
909:
907:
883:
882:
878:
868:
866:
850:
849:
845:
838:
825:
824:
820:
815:
798:
733:
717:
713:
709:
694:
692:
683:
679:
677:methyl chloride
672:
669:
663:
646:
642:
623:
615:benzyl chloride
599:
590:When placed in
588:
563:
559:
555:
548:
532:methyl triflate
516:
510:
485:
480:. For example,
477:
470:
463:
459:
449:
433:
425:methylcobalamin
407:
404:
403:
402:
400:
393:
387:
371:
367:
363:
350:
347:
346:
344:
325:
291:
288:
287:
285:
282:
264:
247:
243:
239:
235:
230:
218:
215:
214:
212:
202:
199:
198:
196:
193:
187:
182:
168:
165:
164:
163:
161:
151:
148:
147:
145:
135:
132:
131:
129:
122:
118:
91:
87:
84:
80:
42:
35:
32:
23:
22:
15:
12:
11:
5:
3790:
3788:
3780:
3779:
3774:
3764:
3763:
3757:
3756:
3754:
3753:
3741:
3729:
3717:
3704:
3701:
3700:
3698:
3697:
3692:
3687:
3682:
3676:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3584:Cosmochemistry
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3549:Astrochemistry
3546:
3541:
3535:
3533:
3527:
3526:
3524:
3523:
3518:
3513:
3508:
3503:
3499:
3495:
3490:
3486:
3481:
3476:
3471:
3466:
3461:
3455:
3453:
3447:
3446:
3444:
3443:
3438:
3433:
3429:
3424:
3419:
3414:
3409:
3404:
3402:Formyl radical
3399:
3394:
3388:
3382:
3380:
3372:
3371:
3368:
3367:
3365:
3364:
3359:
3354:
3349:
3344:
3339:
3334:
3332:Methyl acetate
3329:
3324:
3319:
3314:
3309:
3305:
3301:
3297:
3291:
3286:
3281:
3275:
3273:
3263:
3262:
3260:
3259:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3222:Dimethyl ether
3219:
3214:
3208:
3206:
3198:
3197:
3195:
3194:
3189:
3187:Methyl formate
3184:
3179:
3174:
3172:Glycolaldehyde
3169:
3164:
3159:
3154:
3148:
3146:
3138:
3137:
3135:
3134:
3129:
3124:
3119:
3114:
3109:
3107:Glycolonitrile
3104:
3102:Ethylene oxide
3099:
3094:
3093:
3092:
3082:
3076:
3074:
3066:
3065:
3063:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3022:
3018:
3013:
3008:
3003:
3001:Cyclopropenone
2998:
2993:
2988:
2982:
2980:
2972:
2971:
2969:
2968:
2963:
2958:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2918:
2913:
2908:
2903:
2901:Cyanoacetylene
2898:
2893:
2888:
2883:
2876:
2874:
2866:
2865:
2863:
2862:
2857:
2852:
2847:
2842:
2837:
2832:
2827:
2822:
2820:Methyl radical
2817:
2812:
2807:
2802:
2797:
2795:Isocyanic acid
2792:
2787:
2782:
2777:
2772:
2767:
2762:
2760:Isocyanic acid
2757:
2752:
2746:
2744:
2736:
2735:
2733:
2732:
2727:
2722:
2717:
2712:
2707:
2705:Sulfur dioxide
2702:
2697:
2692:
2687:
2682:
2680:Sodium cyanide
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2638:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2597:
2591:
2589:Formyl radical
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2549:Carbon dioxide
2546:
2541:
2536:
2530:
2528:
2522:
2521:
2496:
2494:
2492:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2430:
2425:
2420:
2414:
2409:
2404:
2399:
2397:Iron(II) oxide
2394:
2389:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2328:
2323:
2318:
2312:
2310:
2301:
2295:
2294:
2289:
2287:
2286:
2279:
2272:
2264:
2255:
2254:
2252:
2251:
2250:
2249:
2244:
2232:
2225:
2219:
2216:
2215:
2213:
2212:
2210:Sulfinylamines
2207:
2202:
2197:
2192:
2190:Phosphoramides
2187:
2185:Isothiocyanate
2181:
2179:
2175:
2174:
2171:
2170:
2168:
2167:
2162:
2161:
2160:
2150:
2149:
2148:
2138:
2137:
2136:
2131:
2126:
2121:
2116:
2105:
2103:
2095:
2094:
2092:
2091:
2086:
2080:
2078:
2072:
2071:
2069:
2068:
2063:
2061:Selenenic acid
2058:
2056:Seleninic acid
2053:
2051:Selenonic acid
2048:
2042:
2040:
2034:
2033:
2031:
2030:
2025:
2019:
2017:
2011:
2010:
2008:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1962:
1957:
1952:
1947:
1942:
1937:
1932:
1931:
1930:
1920:
1914:
1912:
1906:
1905:
1903:
1902:
1897:
1892:
1887:
1886:
1885:
1875:
1870:
1865:
1860:
1859:
1858:
1848:
1847:
1846:
1844:Phosphodiester
1835:
1833:
1827:
1826:
1824:
1823:
1818:
1813:
1808:
1803:
1798:
1793:
1788:
1783:
1778:
1773:
1768:
1763:
1758:
1753:
1748:
1743:
1738:
1733:
1728:
1723:
1722:
1721:
1716:
1705:
1703:
1694:
1690:(one element,
1674:
1673:
1670:
1669:
1667:
1666:
1665:
1664:
1654:
1653:
1652:
1647:
1636:
1634:
1630:
1629:
1627:
1626:
1621:
1616:
1615:
1614:
1604:
1603:
1602:
1597:
1592:
1581:
1579:
1573:
1572:
1570:
1569:
1567:Methylenedioxy
1564:
1559:
1558:
1557:
1552:
1542:
1541:
1540:
1535:
1525:
1524:
1523:
1513:
1508:
1502:
1500:
1493:
1471:
1470:
1468:
1467:
1462:
1457:
1456:
1455:
1450:
1440:
1439:
1438:
1433:
1428:
1423:
1418:
1413:
1403:
1402:
1401:
1396:
1386:
1385:
1384:
1379:
1374:
1369:
1364:
1359:
1348:
1346:
1344:(only C and H)
1336:
1335:
1330:
1328:
1327:
1320:
1313:
1305:
1297:
1296:
1283:
1257:
1248:
1232:
1187:
1171:
1130:
1079:
1070:
1027:
997:
988:
937:
925:
917:
876:
843:
836:
817:
816:
814:
811:
810:
809:
804:
797:
794:
772:back-formation
741:Eugene Peligot
732:
729:
721:ethane barrier
690:
662:
659:
651:stereochemical
622:
619:
587:
584:
547:
544:
536:Methanogenesis
512:Main article:
509:
506:
502:carbon dioxide
475:carboxyl group
448:
445:
432:
429:
405:
391:Methyl radical
389:Main article:
386:
385:Methyl radical
383:
377:where M is an
375:
374:
357:methyl halides
337:methyl lithium
281:
278:
262:
251:
250:
228:
189:Main article:
186:
183:
181:
178:
166:
33:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3789:
3778:
3775:
3773:
3770:
3769:
3767:
3752:
3742:
3740:
3730:
3728:
3718:
3716:
3715:
3706:
3705:
3702:
3696:
3693:
3691:
3688:
3686:
3683:
3680:
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3614:Homochirality
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3536:
3534:
3532:
3528:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3496:
3494:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3469:Methoxyethane
3467:
3465:
3462:
3460:
3457:
3456:
3454:
3452:
3448:
3442:
3439:
3437:
3430:
3428:
3425:
3423:
3420:
3418:
3415:
3413:
3410:
3408:
3405:
3403:
3400:
3398:
3395:
3392:
3389:
3387:
3384:
3383:
3381:
3377:
3373:
3363:
3360:
3358:
3355:
3353:
3352:Butyronitrile
3350:
3348:
3345:
3343:
3340:
3338:
3335:
3333:
3330:
3328:
3327:Ethyl formate
3325:
3323:
3320:
3318:
3315:
3313:
3306:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3276:
3274:
3272:
3264:
3258:
3255:
3253:
3252:Propionitrile
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3209:
3207:
3205:
3199:
3193:
3190:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3149:
3147:
3145:
3139:
3133:
3132:Vinyl alcohol
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3091:
3090:Vinyl cyanide
3088:
3087:
3086:
3085:Acrylonitrile
3083:
3081:
3078:
3077:
3075:
3073:
3067:
3061:
3058:
3056:
3053:
3051:
3050:Pentynylidyne
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3019:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2987:
2984:
2983:
2981:
2979:
2973:
2967:
2964:
2962:
2959:
2957:
2954:
2952:
2949:
2947:
2946:Methylenimine
2944:
2942:
2939:
2937:
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2881:
2878:
2877:
2875:
2873:
2867:
2861:
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2825:Propynylidyne
2823:
2821:
2818:
2816:
2815:Methyl cation
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2775:Fulminic acid
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2748:
2747:
2745:
2743:
2737:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2650:Nitrous oxide
2648:
2646:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2601:
2598:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2544:Amino radical
2542:
2540:
2537:
2535:
2532:
2531:
2529:
2527:
2523:
2518:
2509:
2500:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2474:Sodium iodide
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2434:
2431:
2429:
2426:
2424:
2421:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2387:
2384:
2382:
2379:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2356:Cyano radical
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2336:Carbon cation
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2313:
2311:
2309:
2305:
2302:
2300:
2296:
2292:
2285:
2280:
2278:
2273:
2271:
2266:
2265:
2262:
2248:
2245:
2243:
2240:
2239:
2238:
2237:
2233:
2231:
2230:
2226:
2221:
2220:
2217:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2182:
2180:
2176:
2166:
2163:
2159:
2156:
2155:
2154:
2151:
2147:
2144:
2143:
2142:
2139:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2111:
2110:
2107:
2106:
2104:
2102:
2101:
2096:
2090:
2089:Telluroketone
2087:
2085:
2082:
2081:
2079:
2077:
2073:
2067:
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2043:
2041:
2039:
2035:
2029:
2026:
2024:
2021:
2020:
2018:
2016:
2012:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1975:Sulfonic acid
1973:
1971:
1968:
1966:
1965:Sulfinic acid
1963:
1961:
1960:Thiosulfonate
1958:
1956:
1953:
1951:
1950:Thiosulfinate
1948:
1946:
1945:Sulfenic acid
1943:
1941:
1938:
1936:
1933:
1929:
1926:
1925:
1924:
1921:
1919:
1916:
1915:
1913:
1911:
1907:
1901:
1900:Phosphaallene
1898:
1896:
1895:Phosphaalkyne
1893:
1891:
1890:Phosphaalkene
1888:
1884:
1881:
1880:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1857:
1854:
1853:
1852:
1849:
1845:
1842:
1841:
1840:
1837:
1836:
1834:
1832:
1828:
1822:
1819:
1817:
1814:
1812:
1809:
1807:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1784:
1782:
1779:
1777:
1774:
1772:
1769:
1767:
1764:
1762:
1759:
1757:
1754:
1752:
1749:
1747:
1744:
1742:
1739:
1737:
1734:
1732:
1729:
1727:
1724:
1720:
1717:
1715:
1712:
1711:
1710:
1707:
1706:
1704:
1702:
1698:
1695:
1675:
1663:
1660:
1659:
1658:
1655:
1651:
1648:
1646:
1643:
1642:
1641:
1638:
1637:
1635:
1631:
1625:
1622:
1620:
1617:
1613:
1610:
1609:
1608:
1605:
1601:
1598:
1596:
1593:
1591:
1588:
1587:
1586:
1583:
1582:
1580:
1578:
1574:
1568:
1565:
1563:
1562:Ethylenedioxy
1560:
1556:
1553:
1551:
1548:
1547:
1546:
1543:
1539:
1536:
1534:
1531:
1530:
1529:
1526:
1522:
1519:
1518:
1517:
1514:
1512:
1509:
1507:
1504:
1503:
1501:
1497:
1494:
1488:
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1208:on 2010-07-14
1204:
1197:
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1107:
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1090:
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1038:
1031:
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1011:
1007:
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892:
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837:0-471-60180-2
833:
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805:
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800:
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791:
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783:
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777:
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769:
764:
760:) "wine" and
759:
754:
750:
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738:
730:
728:
726:
722:
708:
704:
700:
689:
678:
668:
660:
658:
656:
652:
640:
636:
632:
628:
621:Chiral methyl
620:
618:
616:
612:
608:
605:
604:photochemical
597:
593:
585:
583:
581:
577:
573:
569:
553:
546:Deprotonation
545:
543:
541:
537:
533:
529:
528:methyl iodide
525:
521:
515:
507:
505:
503:
499:
495:
491:
483:
476:
469:
458:
454:
446:
444:
442:
438:
430:
428:
426:
422:
418:
414:
398:
392:
384:
382:
380:
362:
361:
360:
358:
342:
338:
333:
331:
323:
319:
315:
311:
307:
303:
299:
279:
277:
275:
270:
268:
260:
256:
255:methyl iodide
234:
233:
232:
226:
210:
192:
185:Methyl cation
184:
179:
177:
175:
159:
143:
140:), methylium
127:
116:
112:
108:
104:
100:
96:
78:
74:
70:
66:
63:derived from
62:
58:
54:
45:
39:
30:
19:
18:Carbon cation
3772:Alkyl groups
3707:
3690:Spectroscopy
3544:Astrobiology
3397:Formaldehyde
3289:Benzonitrile
3080:Acetaldehyde
3035:Methanethiol
2986:Acetonitrile
2891:Carbodiimide
2770:Formaldehyde
2765:Cyanoethynyl
2616:Iron cyanide
2611:Hydroperoxyl
2412:Nitric oxide
2234:
2227:
2141:Vinyl halide
2098:
2028:Borinic acid
2023:Boronic acid
2000:Thioxanthate
1356:
1340:Hydrocarbons
1291:
1286:
1278:
1270:
1266:
1260:
1251:
1235:
1210:. Retrieved
1203:the original
1190:
1174:
1147:
1143:
1133:
1096:
1092:
1082:
1073:
1040:
1036:
1030:
1005:
1001:
991:
954:
950:
940:
920:
908:. Retrieved
889:
879:
867:. Retrieved
856:
846:
827:
821:
788:term for an
781:
780:
767:
757:
734:
702:
698:
687:
670:
624:
607:chlorination
589:
576:biosynthesis
549:
517:
494:benzoic acid
482:permanganate
468:formyl group
450:
437:substituents
434:
394:
379:alkali metal
376:
339:and related
334:
283:
280:Methyl anion
271:
267:nucleophiles
252:
194:
156:) or methyl
102:
57:methyl group
56:
50:
43:
3664:Outer space
3574:Cosmic dust
3539:Abiogenesis
3451:Unconfirmed
3407:Heavy water
3247:Ethanethiol
3162:Cyanoallene
3152:Acetic acid
3122:Methylamine
3006:Diacetylene
2921:Formic acid
2911:Cyanomethyl
2569:Diazenylium
2559:CCP radical
2435:(molecular)
2419:(molecular)
2388:(molecular)
2205:Thiocyanate
2200:Sulfonamide
2165:Perchlorate
2153:Acyl halide
2114:Fluoroethyl
1995:Thionoester
1883:Phosphonium
1868:Phosphinate
1863:Phosphonous
1851:Phosphonate
1550:Hydroperoxy
1372:Cyclopropyl
1150:(1): 6â21.
807:Methylation
747:" from the
655:biochemical
639:acetic acid
580:Fatty acids
540:epigenetics
514:Methylation
508:Methylation
427:varieties.
421:radical SAM
395:The methyl
320:; only the
257:and methyl
253:Similarly,
231:2 pathway:
225:protonation
107:hydrocarbon
99:abbreviated
29:Ethyl group
3766:Categories
3579:Cosmic ray
3521:Silylidyne
3484:Hemolithin
3459:Anthracene
3376:Deuterated
3357:Pyrimidine
3167:Ethanimine
3030:Ketenimine
2886:Butadiynyl
2710:Thioformyl
2564:Chloronium
2109:Haloalkane
1980:Thioketone
1935:Persulfide
1831:Phosphorus
1796:Isocyanate
1786:Isonitrile
1687:or oxygen
1685:hydrogen,
1681:not being
1662:Orthoester
1555:Dioxiranes
1533:Enol ether
1421:1-Propenyl
1212:2013-11-26
813:References
665:See also:
568:carbanions
431:Reactivity
328:) and the
304:) and its
3511:Phosphine
3379:molecules
3312:fullerene
3212:Acetamide
3016:Formamide
2896:Cyanamide
2750:Acetylene
2725:Tricarbon
2636:Methylene
2621:Isoformyl
2526:Triatomic
2299:Molecules
2242:inorganic
2076:Tellurium
1990:Thioester
1955:Sulfoxide
1940:Disulfide
1928:Sulfonium
1878:Phosphine
1856:Phosphite
1839:Phosphate
1771:Carbamate
1746:Hydrazone
1679:element,
1677:Only one
1650:Anhydride
1389:Methylene
1166:0890-9369
1065:106409337
745:methylene
731:Etymology
627:deuterium
453:oxidation
447:Oxidation
413:dimerizes
318:superbase
209:gas phase
191:Methenium
75:to three
3498:Linear C
3479:Graphene
3391:Ammonium
3192:Acrolein
3055:Propynal
3040:Methanol
3011:Ethylene
2880:Ammonium
2655:Nitroxyl
2479:Sulfanyl
2423:Imidogen
2417:Nitrogen
2386:Hydrogen
2331:Argonium
2308:Diatomic
2223:See also
2158:Chloride
2084:Tellurol
2038:Selenium
2005:Xanthate
1719:Ammonium
1701:Nitrogen
1683:carbon,
1640:Carboxyl
1607:Aldehyde
1595:Acryloyl
1577:carbonyl
1481:hydrogen
1436:Cumulene
1221:cite web
1125:29743234
1057:30964644
1022:12797825
983:30034765
904:Archived
863:Archived
858:Mashable
796:See also
776:methanol
661:Rotation
613:to give
592:benzylic
520:reagents
364:2 M + CH
259:triflate
115:molecule
95:formulas
77:hydrogen
3644:Kerogen
3531:Related
3474:Glycine
3427:Propyne
3386:Ammonia
3284:Benzene
3279:Acetone
3271:or more
3242:Propene
3227:Ethanol
3117:Propyne
2936:Methane
2805:Ketenyl
2755:Ammonia
2247:organic
2046:Selenol
1970:Sulfone
1923:Sulfide
1821:NONOate
1816:Nitroso
1806:Nitrite
1801:Nitrate
1791:Cyanate
1781:Nitrile
1766:Amidine
1761:Imidate
1731:Nitrene
1726:Hydrazo
1714:Enamine
1645:Acetoxy
1633:carboxy
1600:Benzoyl
1538:Epoxide
1521:Methoxy
1511:Alcohol
1465:Carbene
1399:Methine
1116:6036201
974:6024202
910:27 June
869:27 June
784:is the
667:Rotamer
631:tritium
611:toluene
596:allylic
552:acetone
498:protons
490:toluene
397:radical
368:X â MCH
158:radical
105:. This
65:methane
3695:Tholin
3516:Pyrene
2961:Silane
2931:Ketene
2433:Oxygen
2146:Iodide
2066:Selone
1910:Sulfur
1619:Ketone
1612:Ketene
1590:Acetyl
1545:Peroxy
1516:Alkoxy
1506:Acetal
1487:oxygen
1476:carbon
1460:Alkyne
1453:Benzyl
1448:Phenyl
1431:Allene
1426:Crotyl
1406:Alkene
1394:Bridge
1382:Pentyl
1367:Propyl
1357:Methyl
1275:page 9
1164:
1123:
1113:
1063:
1055:
1020:
981:
971:
891:Nature
834:
802:AdoMet
790:alkane
782:Methyl
707:ethane
643:CHDTCO
635:chiral
530:, and
473:, and
417:ethane
298:ketene
142:cation
93:). In
73:bonded
69:carbon
59:is an
3681:(PAH)
3269:atoms
3204:atoms
3144:atoms
3142:Eight
3072:atoms
3070:Seven
2978:atoms
2872:atoms
2742:atoms
2730:Water
2660:Ozone
2602:(HNC)
2596:(HCN)
2178:Other
2015:Boron
1985:Thial
1918:Thiol
1811:Nitro
1776:Imide
1756:Amide
1741:Oxime
1736:Imine
1709:Amine
1657:Ester
1624:Ynone
1528:Ether
1499:R-O-R
1474:Only
1416:Allyl
1411:Vinyl
1377:Butyl
1362:Ethyl
1352:Alkyl
1292:xylo-
1206:(PDF)
1199:(PDF)
1061:S2CID
758:methy
749:Greek
486:âCOOH
478:âCOOH
441:acids
126:anion
71:atom
61:alkyl
3202:Nine
2870:Five
2780:HCCN
2740:Four
2700:SiNC
2100:Halo
1585:Acyl
1485:and
1443:Aryl
1227:link
1162:ISSN
1121:PMID
1053:PMID
1018:PMID
979:PMID
912:2023
871:2023
832:ISBN
778:").
768:hÈłlÄ
753:ÎŒÎΞÏ
739:and
574:and
500:and
471:âCHO
451:The
423:and
372:+ MX
302:torr
55:, a
44:blue
3493:NCO
3393:ion
3300:, C
3267:Ten
2976:Six
2882:ion
1751:Azo
1241:doi
1180:doi
1152:doi
1111:PMC
1101:doi
1097:293
1045:doi
1041:119
1010:doi
1006:103
969:PMC
959:doi
930:doi
896:doi
763:áœÎ»Î·
695:RâC
673:RâC
600:CâH
594:or
556:(CH
492:to
460:âCH
415:to
326:LiO
314:mol
119:âCH
101:as
51:In
3768::
3310:70
3302:60
3298:60
3296:(C
3021:HC
1483:,
1478:,
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902:.
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861:.
855:.
727:.
714:CH
710:CH
684:Cl
680:CH
617:.
578:.
564:CO
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526:,
466:,
464:OH
443:.
401:CH
381:.
359::
345:CH
310:kJ
286:CH
276:.
269:.
244:OH
236:CH
213:CH
197:CH
162:CH
146:CH
130:CH
103:Me
88:CH
81:CH
3500:5
3491:2
3489:H
3436:D
3434:2
3432:N
3308:C
3025:N
3023:4
2645:H
2643:2
2641:N
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2269:v
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