Electrophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(thq)2CH+		E Param.: -8.22	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
(tol)2CH+		E Param.: 3.63	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
1,1,3-triphenylallylium ion		E Param.: 0.98, Deviation: ±0.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,1,3-triphenylpropyn-1-ylium-Cr(CO)3		E Param.: -0.25, Deviation: ±0.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,1,3-tris(4-(dimethylamino)phenyl)allylium ion		E Param.: -9.84, Deviation: ±0.21	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,1-bis(4-dimethylaminophenyl)-3-phenylallylium ion		E Param.: -8.97, Deviation: ±0.32	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,1-dianisyl-3-phenylallylium ion		E Param.: -2.67, Deviation: ±0.30	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,2-diaza-1,3-diene 1a	DMSO	E Param.: -13.28	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1b	DMSO	E Param.: -13.90	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1c	DMSO	E Param.: -14.91	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1d	DMSO	E Param.: -15.38	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1e	MeOH	E Param.: -14.90	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,2-diaza-1,3-diene 1f	MeOH	E Param.: -15.30	Chem. Eur. J. 2010, 16, 12008-12016 10.1002/chem.201000828
1,3,5-trinitrobenzene		E Param.: -13.19, Deviation: ±0.45	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
1,3-bis(2,4,6-trimethylphenyl)but-1-ylium ion		E Param.: 6.16	Macromolecules 2005, 38, 33-40 10.1021/ma048389o
1,3-diphenylpropyn-1-ylium-Cr(CO)3		E Param.: 1.07, Deviation: ±0.30	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,3-dithianylium ion		E Param.: -2.14, Deviation: ±0.07	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1,4-dioxaspiro[4.5]decan-8-one (in DMSO)	DMSO	E Param.: -18.20	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
1-(4-chlorophenyl)cyclopent-2-enylium ion		E Param.: 3.20, Deviation: ±0.37	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-(tert-butyl)-2-cinnamoyl-3-methyl-1H-imidazol-3-ium	DMSO	E Param.: -11.80	Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...]
1-methyl-3-((julolidin-9-yl)methylene)-3H-indol-1-ium ion		E Param.: -7.79	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
1-methyl-3-(4-methylbenzylidene)-3H-indol-1-ium ion		E Param.: -2.19	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
1-methylpiperidin-4-one (in DMSO)	DMSO	E Param.: -18.40	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
1-methylsulfanylpropan-2-one (in DMSO)	DMSO	E Param.: -15.60	J. Am. Chem. Soc. 2018, 140, 5500-5515 10.1021/jacs.8b01657
1-phenyl-propyn-1-ylium-Co2(CO)5(PPh3)		E Param.: -6.19, Deviation: ±0.44	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-phenyl-proyn-ylium-Co2(CO)6		E Param.: -0.97, Deviation: ±0.08	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-phenylcyclopent-2-enylium ion		E Param.: 2.89, Deviation: ±0.25	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-phenylprop-2-en-1-one (in DMSO)	DMSO	E Param.: -15.25	J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106
2,2,4-trichloro-1(2H)-naphthalenone	MeCN	E Param.: -11.24	Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j
2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one	MeCN	E Param.: -6.75	Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j
2,4-dinitrothiophene		E Param.: -12.33, Deviation: ±0.11	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
2,5-dichloroquinone (C-Cl)		E Param.: -16.11	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
2,5-dichloroquinone (C-H)		E Param.: -12.28	J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b
2,6-di-tert-butyl-4-(2,2,2-trifluoroethylidene)cyclohexa-2,5-dien-1-one	DMSO	E Param.: -11.68	Eur. J. Org. Chem. 2020, , 3812-3817 10.1002/ejoc.202000295
2,6-di-tert-butyl-4-(methoxymethylene)cyclohexa-2,5-dien-1-one		E Param.: -15.10	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-dien-1-one		E Param.: -13.68	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dien-1-one		E Param.: -11.17	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
2,6-di-tert.butyl-4-(3,5-difluorobenzylidene)cyclohexa-2,5-dienone		E Param.: -14.50	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(3-fluorobenzylidene)cyclohexa-2,5-dienone		E Param.: -15.03	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-di-tert.butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-dienone		E Param.: -14.36	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-dimethoxy-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone		E Param.: -17.18	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-dimethoxy-4-(4-methoxybenzylidene)cyclohexa-2,5-dienone		E Param.: -16.38	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-dimethyl-4-(4-(dimethylamino)benzylidene)cyclohexa-2,5-dienone		E Param.: -16.36	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2,6-diphenyl-4-benzylidenecyclohexa-2,5-dienone		E Param.: -11.87	Eur. J. Org. Chem. 2009, , 3203-3211 10.1002/ejoc.200900299
2-(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)acetonitrile		E Param.: -11.88	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
2-(4-methoxybenzylidene)-1,3-dithiane 1,1,3,3-tetraoxide	DMSO	E Param.: -14.55	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
2-(4-methoxybenzylidene)benzo[d][1,3]dithiole 1,1,3,3-tetraoxide	DMSO	E Param.: -13.02	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
2-(4-methoxyphenyl)chromenylium ion		E Param.: -4.95, Deviation: ±0.06	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(p-(dimethylamino)benzylidene)-indan-1,3-dione		E Param.: -13.56	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
2-(p-methoxybenzylidene)-indan-1,3-dione		E Param.: -11.32	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
2-benzylidene-indan-1,3-dione		E Param.: -10.11	Org. Biomol. Chem. 2007, 5, 3020-3026 10.1039/b708025e
2-benzylidenebenzo[d][1,3]dithiole 1,1,3,3-tetraoxide	DMSO	E Param.: -11.78	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
2-cinnamoyl-1,3-dimethyl-1H-imidazol-3-ium	DMSO	E Param.: -11.52	Angew. Chem. Int. Ed. 2012, 51, 5234-5238 10.1002/anie.201109042
2-cinnamoyl-1-(2,6-dimethoxyphenyl)-3-methyl-1H-imidazol-3-ium	DMSO	E Param.: -12.02	Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...]
2-cinnamoyl-1-(4-methoxyphenyl)-3-methyl-1H-imidazol-3-ium	DMSO	E Param.: -11.79	Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...]
2-cinnamoyl-1-mesityl-3-methyl-1H-imidazol-3-ium	DMSO	E Param.: -11.48	Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...]
2-cinnamoyl-3-methyl-1-(perfluorophenyl)-1H-imidazol-3-ium	DMSO	E Param.: -10.09	Top. Catal. 2018, 61, 585-590 10.1007/s11244-018-0[...]
2-methylcyclohexenone	DMSO	E Param.: -27.50	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
2-methylcyclopentenone	DMSO	E Param.: -22.10	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
2-phenyl-1,3-dithianylium ion		E Param.: -6.43, Deviation: ±0.04	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-phenyl-1,3-dithiolan-2-ylium ion		E Param.: -5.91, Deviation: ±0.33	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-phenylethene-1-sulfonyl fluoride	DMSO	E Param.: -16.63	Angew. Chem. Int. Ed. 2016, 55, 12664-12667 10.1002/anie.201601875
3,6-dinitro-1-tosyl-1H-indole		E Param.: -12.90	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
3-(4-(dimethylamino)benzylidene)-1-methyl-3H-indol-1-ium ion		E Param.: -6.26	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
3-(4-methoxybenzylidene)-1-methyl-3H-indol-1-ium iom		E Param.: -3.02	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
3-(trimethylsilyl)propyn-1-ylium-Co2(CO)6		E Param.: -1.60, Deviation: ±0.34	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
3-benzylidene-1-methyl-3H-indol-1-ium ion		E Param.: -1.80	J. Org. Chem. 2015, 80, 8643-8656 10.1021/acs.joc.5b01298
3-chloro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-fluoro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-methoxy-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
3-methylcyclohexenone	DMSO	E Param.: -29.60	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-methylcyclopentenone	DMSO	E Param.: -28.90	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-methylenedihydrofuranone	DMSO	E Param.: -19.40	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-methylenetetrahydropyran-2-one	DMSO	E Param.: -19.50	Chem. Sci. 2021, 12, 4850-4865 10.1039/D0SC06628A
3-nitro-1-tosyl-1H-indole		E Param.: -14.87	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
3-phenylpropyn-1-ylium-Co2(CO)6		E Param.: -1.58, Deviation: ±0.58	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4,6-dinitrobenzofurazan		E Param.: -5.46, Deviation: ±0.36	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4,6-dinitrobenzofuroxan		E Param.: -5.06	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
4,6-dinitrotetrazolopyridine		E Param.: -4.67, Deviation: ±0.30	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4-(2,2-bis(phenylsulfonyl)vinyl)-N,N-dimethylaniline	DMSO	E Param.: -16.53	Chem. Asian J. 2012, 7, 1401-1407 10.1002/asia.201101046
4-aza-6-nitrobenzofuroxan		E Param.: -5.86, Deviation: ±0.36	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4-benzylidene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one		E Param.: -15.58	Chem. Eur. J. 2025, 31, e202501224 10.1002/chem.202501224
4-bromo-3-nitro-1-tosyl-1H-indole		E Param.: -14.60	Chem. Commun. 2021, 57, 10071-10074 10.1039/d1cc04074j
4-bromo-<i>trans-beta</i>-nitrostyrene		E Param.: -13.37	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-chlorobenzaldehyde-boron trichloride complex		E Param.: 1.44, Deviation: ±0.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
4-cyano-6-nitro-benzofuroxane		E Param.: -6.41, Deviation: ±0.38	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4-cyano-<i>trans-beta</i>-nitrostyrene		E Param.: -12.61	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-fluoro-benzaldehyde (in DMSO)	DMSO		J. Am. Chem. Soc. 2011, 133, 8240-8251 10.1021/ja200820m
4-methoxy-<i>trans-beta</i>-nitrostyrene		E Param.: -14.70	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-methyl-<i>trans-beta</i>-nitrostyrene		E Param.: -14.23	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-nitro-6-(trifluoromethylsulfonyl)benzofuroxan		E Param.: -4.91, Deviation: ±0.31	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
4-nitro-<i>trans-beta</i>-nitrostyrene		E Param.: -12.37	J. Org. Chem. 2011, 76, 9370-9378 10.1021/jo201678u
4-nitrobenzodifuroxan (NBDF)		E Param.: -6.15	Chem. Eur. J. 2007, 13, 8317-8324 10.1002/chem.200700676
4-phenylbut-3-yn-2-one		E Param.: -16.90	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
5,7,7-trichloro-8(7H)-quinolinone	MeCN	E Param.: -10.48	Org. Lett. 2010, 12, 2238-2241 10.1021/ol100592j
5-methoxyfuroxano[3,4-d]pyrimidine		E Param.: -8.37	J. Phys. Org. Chem. 2003, 16, 431-437 10.1002/poc.606
6-cyano-4-nitrobenzofuroxan		E Param.: -7.01, Deviation: ±0.16	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
6-nitro-tetrazolo[1,5a]pyridine		E Param.: -9.05, Deviation: ±0.12	J. Org. Chem. 2005, 70, 6242-6253 10.1021/jo0505526
9-(4-(dimethylamino)phenyl)-9H-fluoren-9-ylium	dichloromethane	E Param.: -4.51	Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963
9-(4-methoxyphenyl)-9H-fluoren-9-ylium	dichloromethane	E Param.: 0.85	Chem. Eur. J. 2017, 23, 623-630 10.1002/chem.201603963