2311:
1284:
215:
2296:
592:
1577:
735:, respectively, by metathesis of the corresponding organosodium reagent with tetramethylammonium chloride. Since tetramethylammonium cations cannot form a chemical bond to the carbanionic center, these species are believed to contain free carbanions. While the structure of the former was verified by X-ray crystallography almost a century later, the instability of the latter has so far precluded structural verification. The reaction of the putative "
1199:
2257:
223:
1806:
1938:
2219:
1049:
1547:
1779:
1433:
1166:
1107:
1024:
243:
effective charge delocalization. As a consequence, alkyl carbanions with neighboring conjugating groups (e.g., allylic anions, enolates, nitronates, etc.) are generally planar rather than pyramidized. Likewise, delocalized alkenyl carbanions sometimes favor a linear instead of bent geometry. More often, a bent geometry is still preferred for substituted alkenyl anions, though the linear geometry is only
1229:
1462:
1726:
1347:
1905:
1258:
1664:
1988:
1693:
1839:
1759:
1492:
1372:
1402:
1318:
1872:
1606:
1522:
1140:
1078:
1635:
897:(DMSO), which has a broader useful range (~0 to ~35) than values determined in water (~0 to ~14) and better reflect the basicity of the carbanions in typical organic solvents. Values below less than 0 or greater than 35 are indirectly estimated; hence, the numerical accuracy of these values is limited. Aqueous p
2070:
decreases) when the negative charge is delocalized. This effect occurs when the substituents on the carbanion are unsaturated and/or electronegative. Although carbon acids are generally thought of as acids that are much weaker than "classical" Brønsted acids like acetic acid or phenol, the cumulative
904:
values are also commonly encountered in the literature, particularly in the context of biochemistry and enzymology. Moreover, aqueous values are often given in introductory organic chemistry textbooks for pedagogical reasons, although the issue of solvent dependence is often glossed over. In general,
325:
Carbanions, especially ones derived from weak carbon acids that do not benefit sufficiently from the two stabilizing factors listed above, are generally oxygen- and water-sensitive to varying degrees. While some merely degrade and decompose over several weeks or months upon exposure to air, others
371:
In fact, true carbanions (i.e., a species not attached to a stabilizing covalently bound metal) without electron-withdrawing and/or conjugating substituents are not available in the condensed phase, and these species must be studied in the gas phase. For some time, it was not known whether simple
242:
carbanions may deviate from these geometries. Instead of residing in a hybrid orbital, the carbanionic lone pair may instead occupy a p orbital (or an orbital of high p character). A p orbital has a more suitable shape and orientation to overlap with the neighboring π system, resulting in more
367:
sense. However, they are really clusters or complexes containing a polar covalent bond, though with electron density heavily polarized toward the carbon atom. The more electropositive the attached metal atom, the closer the behavior of the reagent is to that of a true carbanion.
399:
was predicted to be negative). Such a species would decompose immediately by spontaneous ejection of an electron and would therefore be too fleeting to observe directly by mass spectrometry. However, in 1978, the methanide anion was unambiguously synthesized by subjecting
3205:
Kütt, Agnes; Rodima, Toomas; Saame, Jaan; Raamat, Elin; Mäemets, Vahur; Kaljurand, Ivari; Koppel, Ilmar A.; Garlyauskayte, Romute Yu.; Yagupolskii, Yurii L.; Yagupolskii, Lev M.; Bernhardt, Eduard; Willner, Helge; Leito, Ivo (2011). "Equilibrium
Acidities of Superacids".
177:
are commonly treated and referred to as "carbanions." This is a convenient approximation, although these species are generally clusters or complexes containing highly polar, but still covalent bonds metal–carbon bonds (M–C) rather than true carbanions.
210:
makes similar predictions. This contrasts with carbocations, which have a preference for unoccupied nonbonding orbitals of pure atomic p character, leading to planar and linear geometries, respectively, for alkyl and alkenyl
646:
are 145 pm with the phenyl ring propellered at an average angle of 31.2°. This propeller shape is less pronounced with a tetramethylammonium counterion. A crystal structure for the analogous diphenylmethanide anion
2419:) and in 1914 he demonstrated how triarylmethyl radicals could be reduced to carbanions by alkali metals The phrase carbanion was introduced by Wallis and Adams in 1933 as the negatively charged counterpart of the
279:), whose negative charge is stabilized by delocalization, has an inversion barrier of only 4 kcal/mol (17 kJ/mol), reflecting stabilization of the linear transition state by better π delocalization.
206:, placement of the carbanionic lone pair electrons in an orbital with significant s character is favorable, accounting for the pyramidalized and bent geometries of alkyl and alkenyl carbanions, respectively.
2310:
525:
are −6, −7.4, −3.6 kcal/mol, respectively) indicating that α substitution is destabilizing. However, relatively modest stabilizing effects can render them bound. For example,
912:
values in water and organic solvent diverge significantly when the anion is capable of hydrogen bonding. For instance, in the case of water, the values differ dramatically: the p
2460:
861:
values allow the prediction of whether a proton transfer process will be thermodynamically favorable: In order for the deprotonation of an acidic species HA with base
557:
stabilization. Gas-phase carbanions that are sp and sp hybridized are much more strongly stabilized and are often prepared directly by gas-phase deprotonation.
2647:
Ellison, G. Barney; Engelking, P. C.; Lineberger, W. C. (April 1978). "An experimental determination of the geometry and electron affinity of methyl radical".
2213:
2-methyloctanoic acid, which could only have formed from likewise optically active 2-methylheptyllithium with the carbon atom linked to lithium the carbanion:
700:≈ 43) was unsuccessful, due to rapid reaction of the formed anion with the THF solvent. The free benzyl anion has also been generated in the solution phase by
3154:
Trummal, Aleksander; Lipping, Lauri; Kaljurand, Ivari; Koppel, Ilmar A.; Leito, Ivo (2016-05-06). "Acidity of Strong Acids in Water and
Dimethyl Sulfoxide".
2071:(additive) effect of several electron accepting substituents can lead to acids that are as strong or stronger than the inorganic mineral acids. For example,
815:
560:
In the condensed phase only carbanions that are sufficiently stabilized by delocalization have been isolated as truly ionic species. In 1984, Olmstead and
158:
2295:
130:
Carbanions have a concentration of electron density at the negatively charged carbon, which, in most cases, reacts efficiently with a variety of
2548:
747:" with water was reported to liberate toluene and tetramethylammonium hydroxide and provides indirect evidence for the claimed formulation.
2005:
Note that acetic acid, ammonia, aniline, ethanol, and hydrogen chloride are not carbon acids, but are common acids shown for comparison.
2190:
The first ever evidence for the existence of chiral organolithium compounds was obtained in 1950. Reaction of chiral 2-iodooctane with
411:
was determined by photoelectron spectroscopy to be +1.8 kcal/mol, making it a bound species, but just barely so. The structure of
3372:
Kapeller, Dagmar (2007). "Preparation of Chiral α-Oxy-methyllithiums of 99% ee and
Determination of Their Configurational Stability".
3089:
Bordwell, G. F.; Matthews, Walter S. (2002-05-01). "Equilibrium acidities of carbon acids. III. Carbon acids in the membrane series".
591:
3031:
847:). As conjugate acid–base pairs, the factors that determine the relative stability of carbanions also determine the ordering of the p
2715:
Olmstead, Marilyn M. (1985). "The isolation and X-ray structures of lithium crown ether salts of the free phenyl carbanions and ".
2691:
2140:
values in the range of 55 to 65. The range of acid dissociation constants for carbon acids thus spans over 70 orders of magnitude.
2890:
2755:
3581:
3561:
2175:, because if the activation barrier for inversion of this geometry is too low any attempt at introducing chirality will end in
790:
if deprotonation results in loss of a proton from a carbon atom. Compared to compounds typically considered to be acids (e.g.,
3318:-2-Methylcyclopropyllithium and Some Observations on the Stereochemistry of their Reactions with Bromine and Carbon Dioxide".
3119:
Russell, Jamie; Roques, Nicolas (1998-11-05). "Effective nucleophilic trifluoromethylation with fluoroform and common base".
3548:
2256:
2228:
On heating the reaction to 0 °C the optical activity is lost. More evidence followed in the 1960s. A reaction of the
2344:
2912:
Kasmai, Hamid S. (June 1999). "A Simple and
Convenient Method for Generation and NMR Observation of Stable Carbanions".
2406:
2168:
2218:
2183:. However, solid evidence exists that carbanions can indeed be chiral for example in research carried out with certain
334:) are unusual in being indefinitely stable under dry air and hydrolyzing only very slowly in the presence of moisture.
786:
Any compound containing hydrogen can, in principle, undergo deprotonation to form its conjugate base. A compound is a
291:
and basic. The basicity and nucleophilicity of carbanions are determined by the substituents on carbon. These include
2777:
Bockrath, Bradley; Dorfman, Leon M. (2002-05-01). "Submicrosecond formation and observation of reactive carbanions".
2147:
compounds enables these compounds to participate in synthetically important C–C bond-forming reactions including the
202:
alkyl, alkenyl/aryl, and alkynyl carbanions assume trigonal pyramidal, bent, and linear geometries, respectively. By
322:
of the charge-bearing carbanion. The greater the s-character of the charge-bearing atom, the more stable the anion.
2941:"pKa values in the undergraduate curriculum: introducing pKa values measured in DMSO to illustrate solvent effects"
2325:
2287:
819:
806:), carbon acids are typically many orders of magnitude weaker, although exceptions exist (see below). For example,
3469:
Wallis, E. S.; Adams, F. H. (1933). "The
Spatial Configuration of the Valences in Tricovalent Carbon Compounds1".
3345:
Walborsky, H. M. (1964). "Cyclopropanes. XV. The
Optical Stability of 1-Methyl-2,2-diphenylcyclopropyllithium".
2492:"The influence of electron-withdrawing substituents on the geometries and barriers to inversion of vinyl anions"
2229:
2361:. Once again in the range of −78 °C to 0 °C the chirality is preserved in this reaction sequence. (
1915:
364:
349:
2133:
well below −10. On the other end of the scale, hydrocarbons bearing only alkyl groups are thought to have p
2410:
541:
anions are also bound, as a result of negative hyperconjugation of the lone pair with the β-substituent (n
2172:
319:
307:
191:
170:
162:
108:
96:
88:
1283:
330:). Among commonly encountered carbanionic reagents in the laboratory, ionic salts of hydrogen cyanide (
214:
3163:
3001:
2593:
2382:
840:
2355:
829:
428:
267:, has an inversion barrier of 27 kcal/mol (110 kJ/mol), while allenyl anion or allenide,
3519:
3187:
2611:
2362:
2180:
2164:
1209:
965:
147:
538:
3389:
3265:
3223:
3179:
3136:
2960:
2894:
2859:
2759:
2697:
2687:
2682:
Blanksby, S. J.; Bowie, J. H. (2005). "Carbanions: formation, structure and thermochemistry".
2664:
2629:
2544:
2511:
1948:
1882:
926:
in DMSO of water is 31.4, reflecting the differing ability of water and DMSO to stabilize the
894:
673:= 32.3), was also obtained. However, the attempted isolation of a complex of the benzyl anion
389:
303:
187:
174:
166:
31:
326:
may react vigorously and exothermically with air almost immediately to spontaneously ignite (
310:
can stabilize the anion. This is especially true when the anion is stabilized as a result of
3509:
3478:
3451:
3420:
3381:
3354:
3327:
3292:
3257:
3215:
3171:
3128:
3098:
3071:
3009:
2952:
2921:
2886:
2851:
2820:
2786:
2751:
2724:
2656:
2619:
2601:
2536:
2503:
2474:
2370:
2366:
2210:
2152:
1769:
1703:
1328:
763:
759:
609:
572:
568:
296:
256:
76:
1576:
372:
alkyl anions could exist as free species; many theoretical studies predicted that even the
222:
3576:
3045:
2390:
2386:
2198:
2086:
2072:
1645:
1443:
1239:
931:
799:
755:
708:
3167:
3005:
2597:
1805:
3241:
Ding, Feizhi; Smith, Jeremy M.; Wang, Haobin (2009). "First-Principles
Calculation of p
3062:
Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution".
2148:
2119:
1965:
1937:
1198:
833:
811:
602:
576:
203:
135:
50:
3132:
2811:[On triphenylmethyl and analogues of triphenylmethyl in the biphenyl series].
2624:
2565:
2491:
1048:
3570:
2507:
2441:
2420:
2240:
2184:
2108:
1816:
1736:
775:
327:
80:
3523:
3283:
Letsinger, Robert L. (1950). "Formation of
Optically Active 1-Methylheptyllithium".
3191:
2470:
1546:
2381:
A carbanionic structure first made an appearance in the reaction mechanism for the
2206:
2191:
2176:
2028:
1778:
1674:
1472:
1432:
1268:
791:
561:
338:
288:
207:
131:
1228:
1165:
1106:
1023:
259:. For instance, calculations indicate that the parent vinyl anion or ethylenide,
3013:
2465:
2431:
2348:
1789:
1557:
1005:
803:
795:
643:
631:
583:
565:
526:
311:
116:
2956:
2586:
Proceedings of the
National Academy of Sciences of the United States of America
1904:
1725:
1346:
3440:"Über Metalladditionen an freie organische Radikale. XII. Über Triarylmethyle"
1663:
1532:
1461:
1357:
1257:
828:
of 49 which may undergo deprotonation in the presence of a superbase like the
814:
sense, since its aqueous solutions are neutral. Nevertheless, it is very weak
751:
701:
533:
anions are bound due to increased s character of the lone pair orbital, while
3455:
3175:
3140:
2964:
2940:
2863:
2855:
2824:
2809:"Ueber Triphenylmethyl und Analoga des Triphenylmethyls in der Biphenylreihe"
2668:
2530:
2515:
2469:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
3514:
3497:
2701:
2478:
2332:
1987:
927:
534:
373:
195:
124:
3442:[On metal addition to free organic radicals. XII. Tryarylmethyls].
3393:
3269:
3227:
3183:
2898:
2763:
2633:
2118:
values that indicate complete or nearly complete proton transfer to water.
1838:
1758:
2686:. Gross, Michael L., Caprioli, R. M. (1st ed.). Amsterdam: Elsevier.
2606:
2540:
2251:
isomer would have indicated that the intermediate carbanion was unstable.
1692:
1491:
17:
3424:
2891:
10.1002/1521-3765(20020715)8:14<3229::AID-CHEM3229>3.0.CO;2-3
2756:
10.1002/1521-3765(20020715)8:14<3229::AID-CHEM3229>3.0.CO;2-3
2283:
2144:
1849:
1587:
1382:
1176:
586:(which forms a stable complex with lithium cations) at low temperatures:
299:. Electronegative atoms adjacent to the charge will stabilize the charge;
3482:
3358:
3331:
3296:
3102:
3075:
2790:
2728:
2660:
2336:
2202:
2123:
1502:
1412:
1371:
1294:
1150:
1117:
1088:
1059:
1034:
807:
331:
143:
104:
92:
84:
3385:
3261:
3219:
2925:
2615:
1616:
550:
530:
445:
Simple primary, secondary and tertiary sp carbanions (e.g., ethanide
401:
154:
100:
43:
3439:
3408:
2839:
2808:
1871:
1605:
2532:
Stereoelectronic
Effects: A Bridge Between Structure and Reactivity
1401:
1317:
2877:
Harder, Sjoerd (2002-07-15). "Schlenk's Early "Free" Carbanions".
1634:
1521:
1139:
1077:
554:
139:
112:
39:
3310:
Applequist, Douglas E. (1961). "The Configurational Stability of
774:
NMR has provided structural and reactivity data for a variety of
234:
isomers that undergo inversion through a linear transition state.
2436:
120:
489:
were subsequently determined to be unbound species (the EAs of
955:
627:
3498:"The first century of physical organic chemistry: A prologue"
2309:
2299:
Optical stability of 1-methyl-2,2-diphenylcyclopropyllithium
2294:
2255:
2217:
590:
404:
to an electric discharge, and the electron affinity (EA) of
247:
less stable, resulting in facile equilibration between the (
758:
in DMSO shows four vinylic protons at 6.5 ppm and two
226:
Vinyl anions are bent. 1,2-Disubstituted vinyl anions have
2985:
Values in the Undergraduate Curriculum: What is the Real p
2566:"Electron Affinity of the Methyl Radical: Structures of CH
2247:-2-methylcyclopropylcarboxylic acid. The formation of the
766:
anion has a single resonance at 5.50 ppm. The use of
2978:
Silverstein, Todd P.; Heller, Stephen T. (2017-04-17). "p
952:
2742:
Harder, S. (2002). "Schlenk's Early "Free" Carbanions".
2063:
As indicated by the examples above, acidity increases (p
854:
values of the corresponding carbon acids. Furthermore, p
750:
One tool for the detection of carbanions in solution is
190:, the negative charge of a carbanion is localized in an
2939:
Heller, Stephen T.; Silverstein, Todd P. (2020-04-23).
363:) are often referred to as "carbanions," at least in a
2171:
the question is whether or not carbanions can display
971:
These values may differ significantly from aqueous p
208:
Valence shell electron pair repulsion (VSEPR) theory
2305:Of recent date are chiral methyllithium compounds:
3248:Values for Organic Acids in Nonaqueous Solution".
2807:Schlenk, W.; Weickel, T.; Herzenstein, A. (1910).
2490:Caramella, Pierluigi; Houk, K. N. (1981-01-01).
2314:Chiral oxymethyllithiums. Bu stands for butyl,
634:results in a red solution and the salt complex
255:) isomers of the (bent) anion through a linear
3444:Berichte der Deutschen Chemischen Gesellschaft
2844:Berichte der Deutschen Chemischen Gesellschaft
2535:. Chichester, UK: John Wiley & Sons, Ltd.
2331:contains a chiral group with a hydrogen and a
711:prepared two red-colored salts, formulated as
3413:Journal of the Chemical Society, Transactions
2564:Marynick, Dennis S.; Dixon, David A. (1977).
2339:group is replaced by lithium to intermediate
642:precipitates at −20 °C. The central C–C
8:
3409:"LXV. An extension of the benzoin synthesis"
934:, the numerical values are comparable: the p
2122:, with three strongly electron-withdrawing
2842:[On benzyl tetramethyl ammonium].
1986:
1936:
1757:
1724:
1691:
1545:
1370:
1282:
1197:
1164:
1022:
3513:
2623:
2605:
2405:in a quest for tetramethylammonium (from
2354:which on reaction with acetic acid gives
2282:-butyllithium followed by quenching with
2201:at −70 °C followed by reaction with
2111:HCNO, are all strong acids with aqueous p
2038:in DMSO was estimated by the correlation
571:of the triphenylmethanide carbanion from
218:An alkyl carbanion is trigonal pyramidal.
27:Ion with a negatively charged carbon atom
3471:Journal of the American Chemical Society
3374:Journal of the American Chemical Society
3347:Journal of the American Chemical Society
3320:Journal of the American Chemical Society
3285:Journal of the American Chemical Society
3091:Journal of the American Chemical Society
2779:Journal of the American Chemical Society
2717:Journal of the American Chemical Society
2649:Journal of the American Chemical Society
2413:
2400:
2396:
2266:In the same manner the reaction of (+)-(
2102:
2098:
2091:
2081:
2077:
1980:
1976:
1972:
1930:
1926:
1922:
1897:
1893:
1889:
1864:
1860:
1856:
1831:
1827:
1823:
1797:
1751:
1747:
1743:
1718:
1714:
1710:
1685:
1681:
1656:
1652:
1627:
1623:
1598:
1594:
1568:
1564:
1539:
1513:
1509:
1483:
1479:
1454:
1450:
1424:
1420:
1393:
1389:
1364:
1339:
1335:
1310:
1306:
1302:
1275:
1250:
1246:
1220:
1216:
1191:
1187:
1183:
1158:
1132:
1128:
1124:
1099:
1095:
1070:
1066:
1041:
1016:
1012:
742:
738:
730:
726:
718:
714:
695:
669:
665:
650:
637:
622:
520:
516:
508:
504:
496:
492:
484:
480:
468:
464:
448:
434:
407:
395:
388:should be an unbound species (i.e., the
359:
355:
344:
274:
270:
262:
221:
213:
67:
63:
3407:Clarke, R. W. L.; Lapworth, A. (1907).
2453:
2013:
595:Formation of the triphenylmethane anion
549:). The same holds true for anions with
2278:-methyl-2,2-diphenylcyclopropane with
919:in water of water is 14.0, while the p
3114:
3112:
3025:
3023:
2802:
2800:
2684:The encyclopedia of mass spectrometry
7:
2838:Schlenk, W.; Holtz, Johanna (1917).
2385:as correctly proposed by Clarke and
2235:of 2-methylcyclopropyl bromide with
431:barrier of 1.3 kcal/mol, while
3156:The Journal of Physical Chemistry A
3030:Evans, D. A.; Ripin, D. H. (2005).
2345:phosphate–phosphorane rearrangement
865:to be thermodynamically favorable (
655:), prepared form diphenylmethane (p
2840:"Über Benzyl-tetramethyl-ammonium"
2813:Justus Liebig's Annalen der Chemie
2466:Compendium of Chemical Terminology
427:) with an H−C−H angle of 108° and
194:hybridized orbital on carbon as a
25:
2260:Stereochemistry of organolithiums
2143:The acidity of the α-hydrogen in
3438:Schlenk, W.; Marcus, E. (1914).
3250:The Journal of Organic Chemistry
3208:The Journal of Organic Chemistry
2529:Alabugin, Igor V. (2016-09-19).
2239:-butyllithium again followed by
1903:
1870:
1837:
1804:
1777:
1662:
1633:
1604:
1575:
1520:
1490:
1460:
1431:
1400:
1345:
1316:
1256:
1227:
1138:
1105:
1076:
1047:
810:is not an acid in the classical
630:at low temperatures followed by
161:. A carbanion is one of several
134:of varying strengths, including
2167:for a carbanion described as a
146:, halogenating reagents (e.g.,
2879:Chemistry – A European Journal
2222:Optically active organolithium
930:anion. On the other hand, for
438:was determined to be planar (D
1:
3560:values at daecr1.harvard.edu
3133:10.1016/S0040-4020(98)00846-1
3064:Accounts of Chemical Research
2994:Journal of Chemical Education
2914:Journal of Chemical Education
2744:Chemistry: A European Journal
762:protons at 3 ppm whereas the
337:Organometallic reagents like
79:. The carbanions formed from
49:Formally, a carbanion is the
3553:Large database of Bordwell p
3547:values at www.chem.wisc.edu
3540:Large database of Bordwell p
2508:10.1016/0040-4039(81)80005-6
2407:tetramethylammonium chloride
2095:, pentacyanocyclopentadiene
423:was found to be pyramidal (C
3014:10.1021/acs.jchemed.6b00623
941:in water is 15, while the p
869:> 1), the relationship p
3598:
3502:Pure and Applied Chemistry
2957:10.1007/s40828-020-00112-z
2369:after derivatization with
2288:retention of configuration
2126:groups, has an estimated p
318:Geometry also affects the
2318:-Pr stands for isopropyl.
2286:resulted in product with
954:Carbon acid acidities by
287:Carbanions are typically
3456:10.1002/cber.19140470256
3176:10.1021/acs.jpca.6b02253
2856:10.1002/cber.19170500143
2825:10.1002/jlac.19103720102
886:These values below are p
707:Early in 1904 and 1917,
169:. In organic synthesis,
127:) anions, respectively.
3515:10.1351/pac199769020211
3496:Tidwell, T. T. (1997).
2479:10.1351/goldbook.C00804
2205:yielded mostly racemic
1916:Hexafluoroacetylacetone
830:Lochmann–Schlosser base
350:methylmagnesium bromide
103:(at an sp carbon), and
75:where B stands for the
46:is negatively charged.
3582:Reactive intermediates
2319:
2300:
2261:
2223:
2209:but also an amount of
596:
564:presented the lithium
235:
219:
171:organolithium reagents
163:reactive intermediates
2607:10.1073/pnas.74.2.410
2541:10.1002/9781118906378
2313:
2298:
2259:
2243:with dry ice yielded
2221:
2031:(MeCN) is −3.7. The p
893:values determined in
594:
320:orbital hybridization
283:Trends and occurrence
225:
217:
111:carbon) are known as
3425:10.1039/CT9079100694
2383:benzoin condensation
2207:2-methylbutyric acid
704:of dibenzylmercury.
341:(hexameric cluster,
198:. As a consequence,
3483:10.1021/ja01336a068
3359:10.1021/ja01070a017
3332:10.1021/ja01465a030
3297:10.1021/ja01166a538
3168:2016JPCA..120.3663T
3127:(45): 13771–13782.
3103:10.1021/ja00811a041
3076:10.1021/ar00156a004
3006:2017JChEd..94..690S
2791:10.1021/ja00825a005
2729:10.1021/ja00293a059
2661:10.1021/ja00476a054
2598:1977PNAS...74..410M
2496:Tetrahedron Letters
990:Structural formula
980:
2365:was determined by
2363:Enantioselectivity
2343:which undergoes a
2320:
2301:
2262:
2224:
2181:nitrogen inversion
2165:molecular geometry
1210:Dimethyl sulfoxide
953:
818:with an estimated
597:
236:
220:
3386:10.1021/ja066183s
3353:(16): 3283–3288.
3262:10.1021/jo802641r
3220:10.1021/jo101409p
3162:(20): 3663–3669.
2926:10.1021/ed076p830
2885:(14): 3229–3232.
2785:(18): 5708–5715.
2750:(14): 3229–3232.
2550:978-1-118-90637-8
2389:in 1907. In 1904
2335:substituent. The
2179:, similar to the
2159:Chiral carbanions
2006:
1997:
1996:
1949:Hydrogen chloride
979:
895:dimethylsulfoxide
390:electron affinity
308:Resonance effects
175:Grignard reagents
167:organic chemistry
151:-bromosuccinimide
32:organic chemistry
16:(Redirected from
3589:
3528:
3527:
3517:
3493:
3487:
3486:
3466:
3460:
3459:
3435:
3429:
3428:
3404:
3398:
3397:
3369:
3363:
3362:
3342:
3336:
3335:
3307:
3301:
3300:
3280:
3274:
3273:
3256:(7): 2679–2691.
3238:
3232:
3231:
3202:
3196:
3195:
3151:
3145:
3144:
3116:
3107:
3106:
3097:(4): 1216–1217.
3086:
3080:
3079:
3059:
3053:
3052:
3050:
3044:. Archived from
3043:
3027:
3018:
3017:
2975:
2969:
2968:
2936:
2930:
2929:
2909:
2903:
2902:
2874:
2868:
2867:
2835:
2829:
2828:
2804:
2795:
2794:
2774:
2768:
2767:
2739:
2733:
2732:
2723:(7): 2174–2175.
2712:
2706:
2705:
2679:
2673:
2672:
2655:(8): 2556–2558.
2644:
2638:
2637:
2627:
2609:
2581:
2580:
2579:
2561:
2555:
2554:
2526:
2520:
2519:
2487:
2481:
2458:
2417:
2404:
2367:NMR spectroscopy
2211:optically active
2169:trigonal pyramid
2153:Michael addition
2106:
2094:
2084:
2057:
2055:
2018:
2004:
1990:
1983:
1940:
1933:
1907:
1900:
1874:
1867:
1841:
1834:
1808:
1801:
1781:
1770:Hydrogen cyanide
1761:
1754:
1728:
1721:
1704:Diethyl malonate
1695:
1688:
1666:
1659:
1637:
1630:
1608:
1601:
1579:
1572:
1549:
1542:
1524:
1517:
1494:
1487:
1464:
1457:
1435:
1428:
1404:
1397:
1374:
1367:
1349:
1342:
1329:Triphenylmethane
1320:
1313:
1286:
1279:
1260:
1253:
1231:
1224:
1201:
1194:
1168:
1161:
1142:
1135:
1109:
1102:
1080:
1073:
1051:
1044:
1026:
1019:
981:
970:
883:(AH) must hold.
864:
800:carboxylic acids
773:
769:
764:cyclopentadienyl
760:methylene bridge
754:. A spectrum of
746:
734:
722:
702:pulse radiolysis
699:
684:
683:
682:
679:
672:
654:
641:
625:
610:triphenylmethane
573:triphenylmethane
524:
512:
500:
488:
472:
460:
459:
458:
455:
437:
422:
421:
420:
417:
410:
398:
387:
386:
385:
382:
362:
352:(ether complex,
347:
297:inductive effect
278:
266:
257:transition state
188:π delocalization
71:
21:
3597:
3596:
3592:
3591:
3590:
3588:
3587:
3586:
3567:
3566:
3559:
3546:
3537:
3532:
3531:
3495:
3494:
3490:
3468:
3467:
3463:
3437:
3436:
3432:
3406:
3405:
3401:
3371:
3370:
3366:
3344:
3343:
3339:
3309:
3308:
3304:
3282:
3281:
3277:
3247:
3240:
3239:
3235:
3204:
3203:
3199:
3153:
3152:
3148:
3118:
3117:
3110:
3088:
3087:
3083:
3070:(12): 456–463.
3061:
3060:
3056:
3048:
3041:
3038:
3029:
3028:
3021:
2991:
2984:
2977:
2976:
2972:
2938:
2937:
2933:
2911:
2910:
2906:
2876:
2875:
2871:
2837:
2836:
2832:
2806:
2805:
2798:
2776:
2775:
2771:
2741:
2740:
2736:
2714:
2713:
2709:
2694:
2681:
2680:
2676:
2646:
2645:
2641:
2578:
2575:
2574:
2573:
2571:
2569:
2563:
2562:
2558:
2551:
2528:
2527:
2523:
2489:
2488:
2484:
2459:
2455:
2450:
2428:
2415:
2411:
2402:
2398:
2394:
2391:Wilhelm Schlenk
2387:Arthur Lapworth
2379:
2199:petroleum ether
2161:
2139:
2132:
2117:
2104:
2100:
2096:
2093:
2089:
2087:tricyanomethane
2083:
2079:
2075:
2073:trinitromethane
2069:
2061:
2060:
2053:
2046:
2039:
2037:
2026:
2019:
2015:
1982:
1978:
1974:
1970:
1932:
1928:
1924:
1920:
1899:
1895:
1891:
1887:
1866:
1862:
1858:
1854:
1833:
1829:
1825:
1821:
1799:
1795:
1753:
1749:
1745:
1741:
1720:
1716:
1712:
1708:
1687:
1683:
1679:
1658:
1654:
1650:
1646:Cyclopentadiene
1629:
1625:
1621:
1600:
1596:
1592:
1570:
1566:
1562:
1541:
1537:
1515:
1511:
1507:
1485:
1481:
1477:
1456:
1452:
1448:
1444:Phenylacetylene
1426:
1422:
1418:
1395:
1391:
1387:
1366:
1362:
1341:
1337:
1333:
1312:
1308:
1304:
1300:
1277:
1273:
1252:
1248:
1244:
1240:Diphenylmethane
1222:
1218:
1214:
1193:
1189:
1185:
1181:
1160:
1156:
1134:
1130:
1126:
1122:
1101:
1097:
1093:
1072:
1068:
1064:
1043:
1039:
1018:
1014:
1010:
999:
977:
969:
962:
948:in DMSO is 18.
947:
940:
932:cyclopentadiene
925:
918:
911:
903:
892:
882:
875:
862:
860:
853:
826:
784:
771:
767:
756:cyclopentadiene
744:
740:
736:
732:
728:
724:
720:
716:
712:
697:
693:
691:
685:from toluene (p
680:
677:
676:
674:
671:
667:
663:
661:
652:
648:
639:
635:
624:
620:
618:
548:
544:
522:
518:
514:
510:
506:
502:
498:
494:
490:
486:
482:
478:
470:
466:
462:
461:, isopropanide
456:
453:
452:
450:
446:
441:
436:
432:
426:
418:
415:
414:
412:
409:
405:
397:
393:
383:
380:
379:
377:
361:
357:
353:
346:
342:
285:
276:
272:
268:
264:
260:
184:
136:carbonyl groups
123:, and alkynyl (
69:
65:
61:
28:
23:
22:
15:
12:
11:
5:
3595:
3593:
3585:
3584:
3579:
3569:
3568:
3565:
3564:
3557:
3551:
3544:
3536:
3535:External links
3533:
3530:
3529:
3508:(2): 211–214.
3488:
3461:
3430:
3399:
3380:(4): 914–923.
3364:
3337:
3326:(4): 862–865.
3302:
3275:
3245:
3233:
3214:(2): 391–395.
3197:
3146:
3108:
3081:
3054:
3051:on 2019-07-02.
3036:
3019:
3000:(6): 690–695.
2989:
2982:
2970:
2931:
2904:
2869:
2850:(1): 274–275.
2830:
2796:
2769:
2734:
2707:
2692:
2674:
2639:
2592:(2): 410–413.
2576:
2567:
2556:
2549:
2521:
2502:(9): 819–822.
2482:
2452:
2451:
2449:
2446:
2445:
2444:
2439:
2434:
2427:
2424:
2378:
2375:
2322:
2321:
2303:
2302:
2264:
2263:
2226:
2225:
2160:
2157:
2149:aldol reaction
2137:
2130:
2120:Triflidic acid
2115:
2067:
2059:
2058:
2051:
2044:
2035:
2024:
2020:The reported p
2012:
2011:
2010:
2009:
2008:
2007:
1999:
1998:
1995:
1994:
1991:
1984:
1968:
1966:Triflidic acid
1962:
1961:
1958:
1955:
1952:
1945:
1944:
1941:
1934:
1918:
1912:
1911:
1908:
1901:
1885:
1883:Meldrum's acid
1879:
1878:
1875:
1868:
1852:
1846:
1845:
1842:
1835:
1819:
1813:
1812:
1809:
1802:
1793:
1786:
1785:
1782:
1775:
1772:
1766:
1765:
1762:
1755:
1739:
1733:
1732:
1729:
1722:
1706:
1700:
1699:
1696:
1689:
1677:
1671:
1670:
1667:
1660:
1648:
1642:
1641:
1638:
1631:
1619:
1613:
1612:
1609:
1602:
1590:
1584:
1583:
1580:
1573:
1560:
1554:
1553:
1550:
1543:
1535:
1529:
1528:
1525:
1518:
1505:
1499:
1498:
1495:
1488:
1475:
1469:
1468:
1465:
1458:
1446:
1440:
1439:
1436:
1429:
1416:
1409:
1408:
1405:
1398:
1385:
1379:
1378:
1375:
1368:
1360:
1354:
1353:
1350:
1343:
1331:
1325:
1324:
1321:
1314:
1298:
1291:
1290:
1287:
1280:
1271:
1265:
1264:
1261:
1254:
1242:
1236:
1235:
1232:
1225:
1212:
1206:
1205:
1202:
1195:
1179:
1173:
1172:
1169:
1162:
1154:
1147:
1146:
1143:
1136:
1120:
1114:
1113:
1110:
1103:
1091:
1085:
1084:
1081:
1074:
1062:
1056:
1055:
1052:
1045:
1037:
1031:
1030:
1027:
1020:
1008:
1002:
1001:
997:
991:
988:
985:
975:
960:
945:
938:
923:
916:
909:
901:
890:
880:
873:
858:
851:
824:
783:
780:
689:
659:
616:
599:
598:
546:
542:
442:point group).
439:
424:
365:retrosynthetic
316:
315:
306:of the anion.
302:the extent of
300:
284:
281:
183:
180:
73:
72:
51:conjugate base
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3594:
3583:
3580:
3578:
3575:
3574:
3572:
3563:
3556:
3552:
3550:
3543:
3539:
3538:
3534:
3525:
3521:
3516:
3511:
3507:
3503:
3499:
3492:
3489:
3484:
3480:
3476:
3472:
3465:
3462:
3457:
3453:
3449:
3445:
3441:
3434:
3431:
3426:
3422:
3418:
3414:
3410:
3403:
3400:
3395:
3391:
3387:
3383:
3379:
3375:
3368:
3365:
3360:
3356:
3352:
3348:
3341:
3338:
3333:
3329:
3325:
3321:
3317:
3313:
3306:
3303:
3298:
3294:
3290:
3286:
3279:
3276:
3271:
3267:
3263:
3259:
3255:
3251:
3244:
3237:
3234:
3229:
3225:
3221:
3217:
3213:
3209:
3201:
3198:
3193:
3189:
3185:
3181:
3177:
3173:
3169:
3165:
3161:
3157:
3150:
3147:
3142:
3138:
3134:
3130:
3126:
3122:
3115:
3113:
3109:
3104:
3100:
3096:
3092:
3085:
3082:
3077:
3073:
3069:
3065:
3058:
3055:
3047:
3040:
3035:
3026:
3024:
3020:
3015:
3011:
3007:
3003:
2999:
2995:
2988:
2981:
2974:
2971:
2966:
2962:
2958:
2954:
2950:
2946:
2942:
2935:
2932:
2927:
2923:
2919:
2915:
2908:
2905:
2900:
2896:
2892:
2888:
2884:
2880:
2873:
2870:
2865:
2861:
2857:
2853:
2849:
2845:
2841:
2834:
2831:
2826:
2822:
2818:
2814:
2810:
2803:
2801:
2797:
2792:
2788:
2784:
2780:
2773:
2770:
2765:
2761:
2757:
2753:
2749:
2745:
2738:
2735:
2730:
2726:
2722:
2718:
2711:
2708:
2703:
2699:
2695:
2693:9780080438504
2689:
2685:
2678:
2675:
2670:
2666:
2662:
2658:
2654:
2650:
2643:
2640:
2635:
2631:
2626:
2621:
2617:
2613:
2608:
2603:
2599:
2595:
2591:
2587:
2583:
2560:
2557:
2552:
2546:
2542:
2538:
2534:
2533:
2525:
2522:
2517:
2513:
2509:
2505:
2501:
2497:
2493:
2486:
2483:
2480:
2476:
2472:
2468:
2467:
2462:
2457:
2454:
2447:
2443:
2442:Nitrile anion
2440:
2438:
2435:
2433:
2430:
2429:
2425:
2423:
2422:
2421:carbonium ion
2418:
2408:
2392:
2388:
2384:
2376:
2374:
2372:
2371:Mosher's acid
2368:
2364:
2360:
2357:
2353:
2350:
2346:
2342:
2338:
2334:
2330:
2327:
2317:
2312:
2308:
2307:
2306:
2297:
2293:
2292:
2291:
2289:
2285:
2281:
2277:
2273:
2269:
2258:
2254:
2253:
2252:
2250:
2246:
2242:
2241:carboxylation
2238:
2234:
2232:
2220:
2216:
2215:
2214:
2212:
2208:
2204:
2200:
2196:
2195:-butyllithium
2194:
2188:
2186:
2185:organolithium
2182:
2178:
2174:
2170:
2166:
2158:
2156:
2154:
2150:
2146:
2141:
2136:
2129:
2125:
2121:
2114:
2110:
2109:fulminic acid
2088:
2074:
2066:
2050:
2043:
2034:
2030:
2023:
2017:
2014:
2003:
2002:
2001:
2000:
1992:
1989:
1985:
1969:
1967:
1964:
1963:
1959:
1956:
1953:
1950:
1947:
1946:
1942:
1939:
1935:
1919:
1917:
1914:
1913:
1909:
1906:
1902:
1886:
1884:
1881:
1880:
1876:
1873:
1869:
1853:
1851:
1848:
1847:
1843:
1840:
1836:
1820:
1818:
1817:Malononitrile
1815:
1814:
1810:
1807:
1803:
1794:
1791:
1788:
1787:
1783:
1780:
1776:
1773:
1771:
1768:
1767:
1763:
1760:
1756:
1740:
1738:
1737:Acetylacetone
1735:
1734:
1730:
1727:
1723:
1707:
1705:
1702:
1701:
1697:
1694:
1690:
1678:
1676:
1673:
1672:
1668:
1665:
1661:
1649:
1647:
1644:
1643:
1639:
1636:
1632:
1620:
1618:
1615:
1614:
1610:
1607:
1603:
1591:
1589:
1586:
1585:
1581:
1578:
1574:
1561:
1559:
1556:
1555:
1551:
1548:
1544:
1536:
1534:
1531:
1530:
1526:
1523:
1519:
1506:
1504:
1501:
1500:
1496:
1493:
1489:
1476:
1474:
1471:
1470:
1466:
1463:
1459:
1447:
1445:
1442:
1441:
1437:
1434:
1430:
1417:
1414:
1411:
1410:
1406:
1403:
1399:
1386:
1384:
1381:
1380:
1376:
1373:
1369:
1361:
1359:
1356:
1355:
1351:
1348:
1344:
1332:
1330:
1327:
1326:
1322:
1319:
1315:
1299:
1296:
1293:
1292:
1288:
1285:
1281:
1272:
1270:
1267:
1266:
1262:
1259:
1255:
1243:
1241:
1238:
1237:
1233:
1230:
1226:
1213:
1211:
1208:
1207:
1203:
1200:
1196:
1180:
1178:
1175:
1174:
1170:
1167:
1163:
1155:
1152:
1149:
1148:
1144:
1141:
1137:
1121:
1119:
1116:
1115:
1111:
1108:
1104:
1092:
1090:
1087:
1086:
1082:
1079:
1075:
1063:
1061:
1058:
1057:
1053:
1050:
1046:
1038:
1036:
1033:
1032:
1028:
1025:
1021:
1009:
1007:
1004:
1003:
996:
992:
989:
986:
983:
982:
974:
967:
963:
959:
951:
950:
949:
944:
937:
933:
929:
922:
915:
908:
900:
896:
889:
884:
879:
872:
868:
857:
850:
846:
844:
838:
837:-butyllithium
836:
831:
827:
823:
817:
816:Brønsted acid
813:
809:
805:
801:
797:
793:
792:mineral acids
789:
781:
779:
777:
776:organolithium
765:
761:
757:
753:
748:
710:
705:
703:
688:
658:
645:
633:
629:
615:
611:
607:
606:-butyllithium
605:
593:
589:
588:
587:
585:
581:
580:-butyllithium
579:
574:
570:
567:
563:
558:
556:
552:
540:
536:
532:
528:
476:
443:
430:
403:
391:
375:
369:
366:
351:
340:
335:
333:
329:
328:pyrophoricity
323:
321:
313:
309:
305:
301:
298:
294:
293:
292:
290:
282:
280:
258:
254:
250:
246:
241:
233:
229:
224:
216:
212:
211:carbocations.
209:
205:
201:
197:
193:
189:
181:
179:
176:
172:
168:
164:
160:
159:proton donors
156:
152:
150:
145:
144:iminium salts
141:
137:
133:
132:electrophiles
128:
126:
122:
118:
114:
110:
106:
102:
98:
94:
90:
86:
82:
81:deprotonation
78:
60:
59:
58:
56:
52:
47:
45:
41:
37:
33:
19:
3554:
3541:
3505:
3501:
3491:
3474:
3470:
3464:
3447:
3443:
3433:
3416:
3412:
3402:
3377:
3373:
3367:
3350:
3346:
3340:
3323:
3319:
3315:
3311:
3305:
3291:(10): 4842.
3288:
3284:
3278:
3253:
3249:
3242:
3236:
3211:
3207:
3200:
3159:
3155:
3149:
3124:
3120:
3094:
3090:
3084:
3067:
3063:
3057:
3046:the original
3033:
2997:
2993:
2992:of Water?".
2986:
2979:
2973:
2948:
2944:
2934:
2917:
2913:
2907:
2882:
2878:
2872:
2847:
2843:
2833:
2816:
2812:
2782:
2778:
2772:
2747:
2743:
2737:
2720:
2716:
2710:
2683:
2677:
2652:
2648:
2642:
2589:
2585:
2559:
2531:
2524:
2499:
2495:
2485:
2464:
2456:
2380:
2358:
2351:
2340:
2328:
2323:
2315:
2304:
2279:
2275:
2271:
2267:
2265:
2248:
2244:
2236:
2230:
2227:
2192:
2189:
2177:racemization
2162:
2142:
2134:
2127:
2112:
2064:
2062:
2048:
2041:
2032:
2029:acetonitrile
2021:
2016:
1675:Nitromethane
1473:Thioxanthene
1269:Acetonitrile
994:
972:
957:
942:
935:
920:
913:
906:
898:
887:
885:
877:
870:
866:
855:
848:
842:
834:
821:
787:
785:
782:Carbon acids
749:
706:
686:
656:
644:bond lengths
613:
603:
600:
577:
559:
474:
444:
370:
354:MeMg(Br)(OEt
339:butyllithium
336:
324:
317:
289:nucleophilic
286:
252:
248:
244:
239:
237:
231:
227:
199:
185:
148:
129:
74:
54:
48:
35:
29:
3477:(9): 3838.
3450:(2): 1664.
3419:: 694–705.
3121:Tetrahedron
3032:"Chem 206 p
2432:Carbocation
2349:phosphorane
2187:compounds.
1790:Acetic acid
1558:Benzoxazole
1006:Cyclohexane
876:(BH) > p
804:acetic acid
796:nitric acid
788:carbon acid
692:in DMSO of
662:in DMSO of
626:= 30.6) in
619:in DMSO of
566:crown ether
527:cyclopropyl
312:aromaticity
304:conjugation
240:delocalized
204:Bent's rule
115:, alkenyl (
55:carbon acid
3571:Categories
2448:References
2399:C][NMe
2047:= 0.98 × p
1533:Chloroform
1358:Fluoroform
841:potassium
752:proton NMR
741:][PhCH
729:][PhCH
632:12-crown-4
584:12-crown-4
477:-butanide
343:[BuLi]
273:C=C=CH ↔ H
66:CH + B → R
18:Carbanions
3141:0040-4020
2965:2199-3793
2951:(2): 15.
2945:ChemTexts
2864:1099-0682
2669:0002-7863
2516:0040-4039
2471:carbanion
2393:prepared
2333:deuterium
2326:phosphate
2173:chirality
2163:With the
928:hydroxide
845:-butoxide
812:Arrhenius
778:species.
717:][CPh
649:[CHPh
539:phenethyl
535:neopentyl
429:inversion
374:methanide
238:However,
200:localized
196:lone pair
125:acetylide
99:carbon),
91:carbon),
42:in which
36:carbanion
3524:98171271
3394:17243828
3270:19275192
3228:21166439
3192:29697201
3184:27115918
2899:12203352
2819:: 1–20.
2764:12203352
2702:55939535
2634:16592384
2437:Enolates
2426:See also
2284:methanol
2145:carbonyl
1957:HCl (g)
1850:Dimedone
1588:Fluorene
1383:Xanthene
1177:Dithiane
1000:in DMSO
987:Formula
737:[NMe
725:[NMe
713:[NMe
636:[CPh
551:benzylic
332:cyanides
245:slightly
182:Geometry
155:diiodine
3164:Bibcode
3002:Bibcode
2594:Bibcode
2395:[Ph
2377:History
2356:alcohol
2337:stannyl
2274:-bromo-
2203:dry ice
2124:triflyl
1951:(Cl–H)
1503:Acetone
1413:Ethanol
1295:Aniline
1151:Ammonia
1118:Toluene
1089:Propene
1060:Benzene
1035:Methane
978:values.
808:benzene
709:Schlenk
601:Adding
555:allylic
251:) and (
186:Absent
157:), and
107:(at an
105:alkynes
95:(at an
93:alkenes
87:(at an
85:alkanes
3577:Anions
3522:
3392:
3314:- and
3268:
3226:
3190:
3182:
3139:
3039:Table"
2963:
2897:
2862:
2762:
2700:
2690:
2667:
2632:
2625:392297
2622:
2614:
2547:
2514:
2233:isomer
2107:, and
2090:HC(CN)
2054:+ 11.6
1993:~ −16
1792:(O–H)
1617:Indene
1415:(O–H)
1297:(N–H)
1153:(N–H)
473:, and
402:ketene
376:anion
277:C−C≡CH
140:imines
101:arenes
70:C + HB
44:carbon
38:is an
3520:S2CID
3316:trans
3188:S2CID
3049:(PDF)
3042:(PDF)
2920:(6).
2616:66197
2612:JSTOR
2461:IUPAC
2409:and
2249:trans
2076:HC(NO
1971:HC(SO
1960:−2.0
1877:10.3
1844:11.1
1811:12.6
1784:12.9
1764:13.3
1731:16.4
1698:17.2
1669:18.0
1640:20.1
1611:22.6
1582:24.4
1552:24.4
1527:26.5
1497:28.6
1467:28.8
1438:29.8
1407:30.0
1377:30.5
1352:30.6
1323:30.6
1289:31.3
1263:32.3
1234:35.1
984:Name
802:like
798:, or
794:like
562:Power
531:cubyl
348:) or
117:vinyl
113:alkyl
53:of a
40:anion
3562:Link
3549:Link
3390:PMID
3266:PMID
3224:PMID
3180:PMID
3137:ISSN
2961:ISSN
2895:PMID
2860:ISSN
2760:PMID
2698:OCLC
2688:ISBN
2665:ISSN
2630:PMID
2570:and
2545:ISBN
2512:ISSN
2324:The
2151:and
2101:(CN)
1954:HCl
1943:2.3
1925:CCO)
1910:7.3
1800:COOH
1774:HCN
1746:CCO)
1538:CHCl
1204:~39
1171:~41
1145:~43
1112:~44
1083:~49
1054:~56
1029:~60
966:DMSO
839:and
770:and
723:and
675:PhCH
621:CHPh
582:and
569:salt
553:and
545:→ σ*
537:and
529:and
295:the
265:C=CH
230:and
173:and
153:and
121:aryl
77:base
34:, a
3510:doi
3479:doi
3452:doi
3421:doi
3382:doi
3378:129
3355:doi
3328:doi
3312:cis
3293:doi
3258:doi
3216:doi
3172:doi
3160:120
3129:doi
3099:doi
3072:doi
3010:doi
2953:doi
2922:doi
2887:doi
2852:doi
2821:doi
2817:372
2787:doi
2752:doi
2725:doi
2721:107
2657:doi
2653:100
2620:PMC
2602:doi
2537:doi
2504:doi
2475:doi
2473:".
2416:CNa
2373:.)
2347:to
2245:cis
2231:cis
2197:in
2027:in
1363:CHF
1215:(CH
964:in
628:THF
608:to
547:C–C
515:(CH
511:CH•
503:(CH
479:(CH
463:(CH
433:•CH
406:•CH
394:•CH
392:of
165:in
119:),
83:of
30:In
3573::
3518:.
3506:69
3504:.
3500:.
3475:55
3473:.
3448:47
3446:.
3417:91
3415:.
3411:.
3388:.
3376:.
3351:86
3349:.
3324:83
3322:.
3289:72
3287:.
3264:.
3254:74
3252:.
3222:.
3212:76
3210:.
3186:.
3178:.
3170:.
3158:.
3135:.
3125:54
3123:.
3111:^
3095:96
3093:.
3068:21
3066:.
3022:^
3008:.
2998:94
2996:.
2959:.
2947:.
2943:.
2918:76
2916:.
2893:.
2881:.
2858:.
2848:50
2846:.
2815:.
2799:^
2783:96
2781:.
2758:.
2746:.
2719:.
2696:.
2663:.
2651:.
2628:.
2618:.
2610:.
2600:.
2590:74
2588:.
2584:.
2572:CH
2543:.
2510:.
2500:22
2498:.
2494:.
2463:,
2412:Ph
2290::
2270:)-
2155:.
2085:,
1975:CF
1929:CH
1921:(F
1861:12
1796:CH
1750:CH
1742:(H
1715:12
1684:NO
1680:CH
1599:10
1595:13
1571:NO
1484:10
1480:13
1427:OH
1394:10
1390:13
1340:16
1336:19
1309:NH
1278:CN
1274:CH
1251:12
1247:13
1223:SO
1157:NH
1131:CH
1040:CH
1017:12
772:Li
768:Li
698:Ph
694:CH
668:Ph
664:CH
612:(p
575:,
523:C•
513:,
501:,
495:CH
491:CH
471:CH
451:CH
447:CH
440:3h
425:3v
413:CH
378:CH
192:sp
138:,
109:sp
97:sp
89:sp
57::
3558:a
3555:K
3545:a
3542:K
3526:.
3512::
3485:.
3481::
3458:.
3454::
3427:.
3423::
3396:.
3384::
3361:.
3357::
3334:.
3330::
3299:.
3295::
3272:.
3260::
3246:a
3243:K
3230:.
3218::
3194:.
3174::
3166::
3143:.
3131::
3105:.
3101::
3078:.
3074::
3037:a
3034:K
3016:.
3012::
3004::
2990:a
2987:K
2983:a
2980:K
2967:.
2955::
2949:6
2928:.
2924::
2901:.
2889::
2883:8
2866:.
2854::
2827:.
2823::
2793:.
2789::
2766:.
2754::
2748:8
2731:.
2727::
2704:.
2671:.
2659::
2636:.
2604::
2596::
2582:"
2577:3
2568:3
2553:.
2539::
2518:.
2506::
2477::
2414:3
2403:]
2401:4
2397:3
2359:4
2352:3
2341:2
2329:1
2316:i
2280:n
2276:l
2272:l
2268:S
2237:s
2193:s
2138:a
2135:K
2131:a
2128:K
2116:a
2113:K
2105:H
2103:5
2099:5
2097:C
2092:3
2082:3
2080:)
2078:2
2068:a
2065:K
2056:.
2052:a
2049:K
2045:a
2042:K
2040:p
2036:a
2033:K
2025:a
2022:K
1981:3
1979:)
1977:3
1973:2
1931:2
1927:2
1923:3
1898:4
1896:O
1894:8
1892:H
1890:6
1888:C
1865:2
1863:O
1859:H
1857:8
1855:C
1832:2
1830:N
1828:2
1826:H
1824:3
1822:C
1798:3
1752:2
1748:2
1744:3
1719:4
1717:O
1713:H
1711:7
1709:C
1686:2
1682:3
1657:6
1655:H
1653:5
1651:C
1628:8
1626:H
1624:9
1622:C
1597:H
1593:C
1569:5
1567:H
1565:7
1563:C
1540:3
1516:O
1514:6
1512:H
1510:3
1508:C
1486:S
1482:H
1478:C
1455:6
1453:H
1451:8
1449:C
1425:5
1423:H
1421:2
1419:C
1396:O
1392:H
1388:C
1365:3
1338:H
1334:C
1311:2
1307:5
1305:H
1303:6
1301:C
1276:3
1249:H
1245:C
1221:2
1219:)
1217:3
1192:2
1190:S
1188:8
1186:H
1184:4
1182:C
1159:3
1133:3
1129:5
1127:H
1125:6
1123:C
1100:6
1098:H
1096:3
1094:C
1071:6
1069:H
1067:6
1065:C
1042:4
1015:H
1013:6
1011:C
998:a
995:K
993:p
976:a
973:K
968:.
961:a
958:K
956:p
946:a
943:K
939:a
936:K
924:a
921:K
917:a
914:K
910:a
907:K
905:p
902:a
899:K
891:a
888:K
881:a
878:K
874:a
871:K
867:K
863:B
859:a
856:K
852:a
849:K
843:t
835:n
832:(
825:a
822:K
820:p
745:]
743:2
739:4
733:]
731:2
727:4
721:]
719:3
715:4
696:3
690:a
687:K
681:2
678:−
670:2
666:2
660:a
657:K
653:]
651:2
647:(
640:]
638:3
623:3
617:a
614:K
604:n
578:n
543:C
521:3
519:)
517:3
509:2
507:)
505:3
499:•
497:2
493:3
487:C
485:3
483:)
481:3
475:t
469:2
467:)
465:3
457:2
454:−
449:3
435:3
419:3
416:−
408:3
396:3
384:3
381:−
360:2
358:)
356:2
345:6
314:.
275:2
271:2
269:H
263:2
261:H
253:Z
249:E
232:Z
228:E
149:N
142:/
68:3
64:3
62:R
20:)
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