Mayr's Database of Reactivity Parameters

C-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles » C-Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
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
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO)
*
 DMSO

N  Param.: 30.82

sN Param.: 0.41		 ** Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
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
cyano((diphenylmethylene)amino)methanide
*
 DMSO

N  Param.: 29.50

sN Param.: 0.50		 * Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
 DMSO

N  Param.: 29.10

sN Param.: 0.50		 * Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
 DMSO

N  Param.: 29.02

sN Param.: 0.49		 ** Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
anion of 2-phenyl-propionitrile (in DMSO)
C9H8N- *
 DMSO

N  Param.: 28.95

sN Param.: 0.58		 *** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
chloro(phenylsulfonyl)methanide (in DMSO)
C7H6ClO2S *
 DMSO

N  Param.: 28.27

sN Param.: 0.42		 *** J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO)
C19H20NO2- *
 DMSO

N  Param.: 27.77

sN Param.: 0.47		 *** Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
2-(4-Br-C6H4)CH(-)CO2Et (in DMSO)
C10H10BrO2 *
 DMSO

N  Param.: 27.62

sN Param.: 0.53		 *** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(3-Cl-C6H4)CH(-)CO2Et (in DMSO)
C10H10ClO2 *
 DMSO

N  Param.: 27.57

sN Param.: 0.53		 *** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-PhCH(-)CO2Et (in DMSO)
C10H11O2 *
 DMSO

N  Param.: 27.54

sN Param.: 0.57		 *** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
2-(diethylamino)-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C11H17N2O *
 DMSO

N  Param.: 27.45

sN Param.: 0.38		 *** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO)
C9H5F3N- *
 DMSO

N  Param.: 27.28

sN Param.: 0.50		 *** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO)
*
 DMSO

N  Param.: 26.95

sN Param.: 0.52		 *** Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)
C7H5Cl2O2S *
 DMSO

N  Param.: 26.90

sN Param.: 0.45		 *** J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
2-ethoxy-2-oxo-1-(pyridin-1-ium-1-yl)ethan-1-ide (in DMSO)
C9H12NO2 *
 DMSO

N  Param.: 26.71

sN Param.: 0.37		 *** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
chloro(phenylsulfonyl)methanide (in DMF)
C7H6ClO2S *
 DMF

N  Param.: 26.64

sN Param.: 0.64		 - Chem. Eur. J. 2008, 14, 6108-6118
10.1002/chem.200800329
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
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)
C7H7N2 *
 DMSO

N  Param.: 25.94

sN Param.: 0.42		 *** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
anion of (benzylsulfonyl)benzene (in DMSO)
C13H11O2S *
 DMSO

N  Param.: 25.77

sN Param.: 0.56		 *** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)
C8H5ClNO2S *
 DMSO

N  Param.: 25.59

sN Param.: 0.51		 *** J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
enolate of 3-isochromanone (in DMSO)
C9H7O2- *
 DMSO

N  Param.: 25.39

sN Param.: 0.54		 *** J. Org. Chem. 2024, 89, 6915-6928
10.1021/acs.joc.4c00277
anion of 2-(4-CN-C6H4)propionitrile (in DMSO)
C10H7N2- *
 DMSO

N  Param.: 25.35

sN Param.: 0.56		 *** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 4-cyanobenzyl-CN (in DMSO)
C9H5N2- *
 DMSO

N  Param.: 25.11

sN Param.: 0.54		 *** J. Org. Chem. 2009, 74, 75-81
10.1021/jo802241x
anion of 1-phenylpropan-2-one (in DMSO)
C9H9O *
 DMSO

N  Param.: 24.99

sN Param.: 0.60		 *** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)
C7H5ClNO4S *
 DMSO

N  Param.: 24.88

sN Param.: 0.49		 *** J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
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
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO)
C14H10F3O2S- *
 DMSO

N  Param.: 24.30

sN Param.: 0.51		 *** Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
potassium indenide (in DMSO)
C9H7K *
 DMSO

N  Param.: 24.16

sN Param.: 0.68		 *** Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
bromo(phenylsulfonyl)methanide (in DMSO)
C7H6BrO2S *
 DMSO

N  Param.: 23.90

sN Param.: 0.62		 *** J. Org. Chem. 2017, 82, 2011-2017
10.1021/acs.joc.6b02844
sodium indenide (in DMSO)
C9H7Na *
 DMSO

N  Param.: 23.74

sN Param.: 0.71		 *** Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
lithium indenide (in DMSO)
C9H7Li *
 DMSO

N  Param.: 23.66

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
2-(4-CN-C6H4)CH(-)CO2Et (in DMSO)
C11H10NO2 *
 DMSO

N  Param.: 23.64

sN Param.: 0.65		 *** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
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-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
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)
C9H10NO2 *
 DMSO

N  Param.: 23.27

sN Param.: 0.70		 *** Eur. J. Org. Chem. 2013, , 4255-4261
10.1002/ejoc.201300265
anion of 1,2-diphenylethanone (in DMSO)
C14H11O *
 DMSO

N  Param.: 23.15

sN Param.: 0.60		 *** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of diethyl 2-butylmalonate (in DMSO)
C11H19O4 *
 DMSO

N  Param.: 23.00

sN Param.: 0.55		 *** Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
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-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
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO)
C14H10NO2S- *
 DMSO

N  Param.: 22.60

sN Param.: 0.57		 *** Org. Biomol. Chem. 2008, 6, 3052-3058
10.1039/b805604h
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
anion of nitroethane (in DMF)
C2H4NO2- *
 DMF

N  Param.: 22.21

sN Param.: 0.48		 *** Chem. Eur. J. 2008, 14, 6108-6118
10.1002/chem.200800329
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-(4-(dimethylamino)pyridin-1-ium-1-yl)-2-oxo-2-phenylethan-1-ide (in DMSO)
C15H17N2O *
 DMSO

N  Param.: 21.61

sN Param.: 0.58		 *** J. Am. Chem. Soc. 2013, 135, 15216-15224
10.1021/ja407885h
anion of nitroethane (in DMSO)
C2H4NO2 *
 DMSO

N  Param.: 21.54

sN Param.: 0.62		 *** J. Org. Chem. 2003, 68, 6880-6886
10.1021/jo0344182
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.[...]
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
Me2S(O)=CH2 (in DMSO)
*
 DMSO

N  Param.: 21.29

sN Param.: 0.47		 *** J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749