Mayr's Database of Reactivity Parameters

C-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles
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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
anion of Meldrum's acid (in water)
C6H7O4-*
 water

N  Param.: 12.06

sN Param.: 0.66		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of dimedone (in water)
C8H11O2-*
 water

N  Param.: 11.77

sN Param.: 0.63		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of acetylacetone (in water)
C5H7O2-*
 water

N  Param.: 13.73

sN Param.: 0.64		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of ethyl acetylacetate (in water)
C6H9O3-*
 water

N  Param.: 15.99

sN Param.: 0.62		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of malononitrile (in water)
C3HN2-*
 water

N  Param.: 19.50

sN Param.: 0.55		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of ethyl cyanoacetate (in water)
C5H6NO2-*
 water

N  Param.: 15.57

sN Param.: 0.58		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of diethyl malonate (in water)
C7H11O4-*
 water

N  Param.: 16.15

sN Param.: 0.66		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of diethyl methylmalonate (in water)
C8H13O4-*
 water

N  Param.: 17.68

sN Param.: 0.50		*J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of 3-methyl acetylacetone (in water)
C6H9O2-*
 water

N  Param.: 14.33

sN Param.: 0.69		***J. Am. Chem. Soc. 2003, 125, 12980-12986
10.1021/ja036838e
anion of nitroethane (in water)
C2H4NO2-*
 water

N  Param.: 11.25

sN Param.: 0.52		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of nitromethane (in water)
CH2NO2-*
 water

N  Param.: 12.06

sN Param.: 0.53		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of 2-nitropropane (in water)
C3H6NO2-*
 water

N  Param.: 10.69

sN Param.: 0.56		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of phenylnitromethane (in H2O)
C7H6NO2-*
 water

N  Param.: 12.05

sN Param.: 0.53		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of p-tolylnitromethane (in water)
C8H8NO2-*
 water

N  Param.: 13.09

sN Param.: 0.50		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-nitrophenyl)nitromethane (in water)
C7H5N2O4-*
 water

N  Param.: 13.58

sN Param.: 0.52		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (3-nitrophenyl)nitromethane (in water)
C7H5N2O4-*
 water

N  Param.: 14.25

sN Param.: 0.46		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of (4-cyanophenyl)nitromethane (in water)
C8H5N2O2-*
 water

N  Param.: 13.23

sN Param.: 0.52		***J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
1,3-dimesityl-1H-imidazol-3-ium-2-ide (in THF)
C21H24N2*
 THF

N  Param.: 21.72

sN 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)
C21H26N2*
 THF

N  Param.: 23.35

sN 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)
C20H15N3*
 THF

N  Param.: 14.07

sN Param.: 0.84		***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
MeO-Breslow 1a
*
 THF

N  Param.: 14.77

sN Param.: 0.80		***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
MeO-Breslow 1b
*
 THF

N  Param.: 10.45

sN Param.: 0.81		***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
MeO-Breslow 1c
*
 THF

N  Param.: 16.61

sN Param.: 0.68		***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
MeO-Breslow 1e
*
 THF

N  Param.: 15.65

sN Param.: 0.52		***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
Dexoxy Breslow intermediate 6
*
 THF

N  Param.: 15.58

sN Param.: 0.57		***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
Desoxy Breslow intermediate 2a
*
 THF

N  Param.: 17.12

sN Param.: 0.80		***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
Desoxy Breslow intermediate 2a'
*
 THF

N  Param.: 14.45

sN Param.: 0.71		***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
Desoxy Breslow intermediate 2b
*
 THF

N  Param.: 13.91

sN Param.: 0.64		***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
Desoxy Breslow intermediate 2b'
*
 THF

N  Param.: 11.42

sN Param.: 0.70		***Angew. Chem. Int. Ed. 2012, 51, 6231-6235
10.1002/anie.201202327
Desoxy Breslow intermediate 2c'
*
 THF

N  Param.: 12.75

sN 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)
C30H32N2O*
 THF

N  Param.: 15.33

sN 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)
C30H34N2O*
 THF

N  Param.: 15.92

sN 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)
C29H23N3O*
 THF

N  Param.: 14.40

sN 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)
C13H16N2*
 THF

N  Param.: 21.50

sN 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)
C8H14N2*
 THF

N  Param.: 16.54

sN 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)
C11H12N2O*
 THF

N  Param.: 20.41

sN 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)
C12H14N2O2*
 THF

N  Param.: 23.00

sN Param.: 0.46		***Org. Lett. 2016, 18, 3566-3569
10.1021/acs.orglett.[...]
1,3-dimethyl-2-methyleneimidazolidine (in THF)
C6H12N2*
 THF

N  Param.: 18.11

sN Param.: 0.68		***J. Org. Chem. 2021, 86, 2974-2985
10.1021/acs.joc.0c02838
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF)
C7H14N2*
 THF

N  Param.: 18.68

sN 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)
C22H26N2*
 THF

N  Param.: 17.80

sN 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
C10H12N2*
 THF

N  Param.: 19.84

sN 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)
C35H39F6N3*
 THF

N  Param.: 21.36

sN 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)
C34H40F3N3*
 THF

N  Param.: 22.30

sN 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)
C34H43N3O*
 THF

N  Param.: 23.55

sN 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)
C42H59N3*
 THF

N  Param.: 20.78

sN 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)
C15H21N3*
 THF

N  Param.: 30.25

sN 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)
C13H25N3*
 THF

N  Param.: 31.92

sN 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)
C33H41N3*
 THF

N  Param.: 22.80

sN 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)
C28H39N3*
 THF

N  Param.: 24.86

sN 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)
C34H31N*
 THF

N  Param.: 26.16

sN Param.: 0.52		***Angew. Chem. Int. Ed. 2024, , e202318283
10.1002/anie.202318283