C-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 8.12 s_N Param.: 0.88	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-13-(ethylthio)-6-styryl-6,12-diazadispiro[4.1.47.25]tridec-12-ene (in MeCN)	MeCN	N Param.: 7.79 s_N Param.: 0.87	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 9.64 s_N Param.: 0.70	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 7.92 s_N Param.: 0.73	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)	MeCN	N Param.: 8.30 s_N Param.: 0.84	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidin-4-one (in MeCN)	MeCN	N Param.: 7.10 s_N Param.: 0.82	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
(E)-2,2,3,5,5-pentamethyl-1-styrylimidazolidine-4-thione (in MeCN)	MeCN	N Param.: 6.49 s_N Param.: 0.83	Chem. Eur. J. 2024, 30, e202302764 10.1002/chem.202302764
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN)	MeCN	N Param.: 19.69 s_N Param.: 0.61	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
anion of nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.02 s_N Param.: 0.61	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of nitroethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of 2-nitropropane (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.20 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of phenylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.51 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of p-tolylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.58 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of (4-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.05 s_N Param.: 0.72	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of (3-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.75 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of (4-cyanophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.92 s_N Param.: 0.74	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of ethyl cyanoacetate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.59 s_N Param.: 0.65	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of malononitrile (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of dimethyl malonate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.66	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of 4-cyanobenzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N Param.: 19.49 s_N Param.: 0.63	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N Param.: 20.72 s_N Param.: 0.58	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.72 s_N Param.: 0.45	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.35 s_N Param.: 0.40	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)	THF	N Param.: 14.07 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1c	THF	N Param.: 16.61 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1e	THF	N Param.: 15.65 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)	THF	N Param.: 15.33 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF)	THF	N Param.: 15.92 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)	THF	N Param.: 14.40 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 21.50 s_N Param.: 0.45	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 16.54 s_N Param.: 0.47	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 20.41 s_N Param.: 0.46	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF)	THF	N Param.: 23.00 s_N Param.: 0.46	Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...]
1,3-dimethyl-2-methyleneimidazolidine (in THF)	THF	N Param.: 18.11 s_N Param.: 0.68	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)	THF	N Param.: 18.68 s_N Param.: 0.63	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF)	THF	N Param.: 17.80 s_N Param.: 0.79	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole	THF	N Param.: 19.84 s_N Param.: 0.58	J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)	THF	N Param.: 21.36 s_N Param.: 0.42	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-Bis(2,6-diisopropylphenyl)-4-methylene-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 22.30 s_N Param.: 0.49	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-Bis(2,6-diisopropylphenyl)-5-(4-methoxyphenyl)-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 23.55 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-Bis(2,6-diisopropylphenyl)-5-methylene-4-(2,4,6-triisopropylphenyl)-4,5-dihydro-1H-1,2,3-triazol-3-ium-4-ide (in THF)	THF	N Param.: 20.78 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-Diisopropyl-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 30.25 s_N Param.: 0.54	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
5-(tert-Butyl)-1,3-diisopropyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 31.92 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-bis(2,6-diisopropylphenyl)-4-methylene-5-phenyl-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 22.80 s_N Param.: 0.60	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1,3-bis(2,6-diisopropylphenyl)-5-methyl-4-methylene-4,5-dihydro-1H-1,2,3-triazol-3-ium-5-ide (in THF)	THF	N Param.: 24.86 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2023, 62, e202309790 10.1002/anie.202309790
1-mesityl-3-methyl-5-methylene-2,4,6-triphenyl-2,5-dihydropyridin-1-ium-2-ide (in THF)	THF	N Param.: 26.16 s_N Param.: 0.52	Angew. Chem. Int. Ed. 2024, , e202318283 10.1002/anie.202318283
anion of Meldrum's acid (in water)	water	N Param.: 12.06 s_N Param.: 0.66	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of dimedone (in water)	water	N Param.: 11.77 s_N Param.: 0.63	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of acetylacetone (in water)	water	N Param.: 13.73 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of ethyl acetylacetate (in water)	water	N Param.: 15.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of malononitrile (in water)	water	N Param.: 19.50 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of ethyl cyanoacetate (in water)	water	N Param.: 15.57 s_N Param.: 0.58	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of diethyl malonate (in water)	water	N Param.: 16.15 s_N Param.: 0.66	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of diethyl methylmalonate (in water)	water	N Param.: 17.68 s_N Param.: 0.50	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of 3-methyl acetylacetone (in water)	water	N Param.: 14.33 s_N Param.: 0.69	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of nitroethane (in water)	water	N Param.: 11.25 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of nitromethane (in water)	water	N Param.: 12.06 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of 2-nitropropane (in water)	water	N Param.: 10.69 s_N Param.: 0.56	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of phenylnitromethane (in H2O)	water	N Param.: 12.05 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in water)	water	N Param.: 13.09 s_N Param.: 0.50	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in water)	water	N Param.: 13.58 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in water)	water	N Param.: 14.25 s_N Param.: 0.46	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in water)	water	N Param.: 13.23 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j