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)
alpha-(N-piperidino)styrene (in MeCN)
C13H17N *
 MeCN

N  Param.: 11.60

sN Param.: 0.80		 * Chem. Eur. J. 2018, 24, 5901-5910
10.1002/chem.201705962
alpha-(N-morpholino)styrene (in MeCN)
C12H15NO *
 MeCN

N  Param.: 10.30

sN Param.: 0.80		 * Chem. Eur. J. 2018, 24, 5901-5910
10.1002/chem.201705962
(p-nitrophenyl)diazomethane
*
 dichloromethane

N  Param.: 7.17

sN Param.: 0.83		 *** J. Am. Chem. Soc. 2018, 140, 16758-16772
10.1021/jacs.8b09995
(p-cyanophenyl)diazomethane
*
 dichloromethane

N  Param.: 7.66

sN Param.: 0.80		 *** J. Am. Chem. Soc. 2018, 140, 16758-16772
10.1021/jacs.8b09995
(p-bromophenyl)diazomethane
*
 dichloromethane

N  Param.: 8.87

sN Param.: 0.82		 *** J. Am. Chem. Soc. 2018, 140, 16758-16772
10.1021/jacs.8b09995
1-(trimethylsiloxy)cyclopentene (in MeCN)
C8H16OSi *
 MeCN

N  Param.: 6.43

sN Param.: 0.89		 *** Chem. Asian J. 2012, 7, 1401-1407
10.1002/asia.201101046
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[...]
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[...]
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[...]
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[...]
cyano((diphenylmethylene)amino)methanide
*
 DMSO

N  Param.: 29.50

sN Param.: 0.50		 * Tetrahedron 2019, 75, 459-463
10.1016/j.tet.2018.1[...]
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN)
C17H20OSi *
 MeCN

N  Param.: 3.00

sN Param.: 0.83		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN)
C12H18OSi *
 MeCN

N  Param.: 5.18

sN Param.: 0.94		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
3-(trimethylsiloxy)-1H-indene (in MeCN)
C12H16OSi *
 MeCN

N  Param.: 7.32

sN Param.: 0.82		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN)
C13H18OSi *
 MeCN

N  Param.: 5.06

sN Param.: 0.91		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
3-pyrrolidino-1H-indene (in MeCN)
C13H15N *
 MeCN

N  Param.: 15.27

sN Param.: 0.93		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN)
C14H17N *
 MeCN

N  Param.: 14.09

sN Param.: 0.66		 *** Synthesis 2019, 51, 1157-1170
10.1055/s-0037-1611634
1-ethoxy-3-(4-nitrophenyl)-1,3-dioxopropan-2-ide (in DMSO)
C11H10NO5- *
 DMSO

N  Param.: 16.26

sN Param.: 0.83		 *** J. Am. Chem. Soc. 2018, 140, 11474-11486
10.1021/jacs.8b07147
Ph3P=CH-CHO (in MeCN)
C20H17OP *
 MeCN

N  Param.: 9.09

sN Param.: 0.74		 *** J. Am. Chem. Soc. 2016, 138, 11272-11281
10.1021/jacs.6b06264
Ph3P=CH-C(O)Me (in MeCN)
C21H19OP *
 MeCN

N  Param.: 10.27

sN Param.: 0.83		 *** J. Am. Chem. Soc. 2016, 138, 11272-11281
10.1021/jacs.6b06264
anion of 4-(trifluoromethyl)benzyl trifluoromethyl sulfone (in MeCN)
C9H5F6O2S *
 MeCN

N  Param.: 16.15

sN Param.: 0.99		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-cyanobenzyl trifluoromethyl sulfone (in MeCN)
C9H5F3NO2S *
 MeCN

N  Param.: 15.62

sN Param.: 0.99		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of 4-nitrobenzyl-CN (in MeCN)
C8H5N2O2 *
 MeCN

N  Param.: 20.10

sN Param.: 0.71		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
anion of (4-NO2-C6H4)CH2SO2Ph (in MeCN)
C13H10NO4S *
 MeCN

N  Param.: 19.90

sN Param.: 0.66		 *** J. Am. Chem. Soc. 2020, 142, 8383-8402
10.1021/jacs.0c01960
3-diazoindolin-2-one
C8H5N3O *
 dichloromethane

N  Param.: 3.16

sN Param.: 1.03		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazoindan-1-one
C9H6N2O *
 dichloromethane

N  Param.: 5.61

sN Param.: 0.65		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazocyclohexanone
C6H8N2O *
 dichloromethane

N  Param.: 3.44

sN Param.: 0.83		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazo-1-tetralone
C10H8N2O *
 dichloromethane

N  Param.: 3.51

sN Param.: 0.86		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazoindandione
C9H4N2O2 *
 dichloromethane

N  Param.: 0.16

sN Param.: 0.86		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazo-1-benzosuberone
C11H10N2O *
 dichloromethane

N  Param.: 2.72

sN Param.: 0.96		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one
C8H4N2OS *
 dichloromethane

N  Param.: 0.40

sN Param.: 0.93		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
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
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C15H22BLiO2 *
 MeCN

N  Param.: 11.00

sN Param.: 0.57		 *** J. Am. Chem. Soc. 2022, 144, 16118-16130
10.1021/jacs.2c06493
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
C12H19N3S *
 MeCN

N  Param.: 9.25

sN Param.: 0.84		 *** Chem. Commun. 2023, 59, 8091-8084
10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
C17H21N3S *
 MeCN

N  Param.: 7.74

sN Param.: 0.87		 *** Chem. Commun. 2023, 59, 8091-8084
10.1039/d3cc01912h
2-((2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in CH2Cl2)
C17H21N3S *
 dichloromethane

N  Param.: 7.06

sN Param.: 1.11		 *** Chem. Commun. 2023, 59, 8091-8084
10.1039/d3cc01912h
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
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
C13H21N3S *
 MeCN

N  Param.: 9.23

sN Param.: 0.74		 *** Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)
C17H24N2S *
 MeCN

N  Param.: 8.12

sN Param.: 0.88		 *** Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764