Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
2-(trimethylsilyl)propene
C6H14Si *
dichloromethane

N  Param.: -1.46

sN Param.: 1.05
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-(pentamethyldisilyl)propene
C8H20Si2 *
dichloromethane

N  Param.: -0.26

sN Param.: 0.95
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-(tris(trimethylsilyl)silyl)propene
C12H32Si4 *
dichloromethane

N  Param.: -0.31

sN Param.: 0.99
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
alpha-(trimethylsilyl)styrene
C11H16Si *
dichloromethane

N  Param.: -1.13

sN Param.: 1.46
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
alpha-(pentamethyldisilyl)styrene
C13H22Si2 *
dichloromethane

N  Param.: 0.61

sN Param.: 1.01
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
beta-(trimethylsilyl)styrene
C11H16Si *
dichloromethane

N  Param.: -0.43

sN Param.: 1.06
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
2-phenyl-allyltrimethylsilane
C12H18Si *
dichloromethane

N  Param.: 5.38

sN Param.: 0.89
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
1-(p-tolyl)-1-(trimethylsilyl)ethene
C12H18Si *
dichloromethane

N  Param.: -0.65

sN Param.: 1.59
*** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide
C18H19NO2S *
dichloromethane

N  Param.: 5.16

sN Param.: 0.85
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide
C23H21NO3S *
dichloromethane

N  Param.: 4.40

sN Param.: 0.86
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
4-methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide
C22H19NO2S *
dichloromethane

N  Param.: 3.85

sN Param.: 0.84
*** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C15H18NO4 *
DMSO

N  Param.: 14.48

sN Param.: 0.86
*** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
5-(4-(methoxy)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C14H15O5 *
DMSO

N  Param.: 15.13

sN Param.: 0.75
*** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
5-benzyl-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C13H13O4 *
DMSO

N  Param.: 15.02

sN Param.: 0.75
*** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C14H12NO4 *
DMSO

N  Param.: 13.79

sN Param.: 0.86
*** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
2,2-dimethyl-5-(4-nitrobenzyl)-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)
C13H12NO6 *
DMSO

N  Param.: 12.02

sN Param.: 1.17
*** Chem. Eur. J. 2014, 20, 11069-11077
10.1002/chem.201403161
(E)-1-styrylpyrrolidine (in CH2Cl2)
C12H15N *
dichloromethane

N  Param.: 12.26

sN Param.: 0.93
*** J. Am. Chem. Soc. 2014, 136, 14263-14269
10.1021/ja508065e
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)
C31H29N *
dichloromethane

N  Param.: 10.19

sN Param.: 1.06
*** J. Am. Chem. Soc. 2014, 136, 14263-14269
10.1021/ja508065e
(E)-1-styryl-2-(triphenylsilyl)pyrrolidine (in CH2Cl2)
C30H29NSi *
dichloromethane

N  Param.: 11.77

sN Param.: 0.98
*** J. Am. Chem. Soc. 2014, 136, 14263-14269
10.1021/ja508065e
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 N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO)
C13H16NO2 *
DMSO

N  Param.: 19.28

sN Param.: 0.65
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)
C11H11O3 *
DMSO

N  Param.: 17.52

sN Param.: 0.74
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of 3-oxo-3-phenylpropanenitrile (in DMSO)
C9H6NO *
DMSO

N  Param.: 16.55

sN Param.: 0.78
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of 1-phenylbutane-1,3-dione (in DMSO)
C10H9O2 *
DMSO

N  Param.: 16.03

sN Param.: 0.86
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of 1,3-diphenylpropane-1,3-dione (in DMSO)
C15H11O2 *
DMSO

N  Param.: 17.46

sN Param.: 0.65
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of 1-phenyl-2-(phenylsulfonyl)ethanone (in DMSO)
C14H11O3S *
DMSO

N  Param.: 17.19

sN Param.: 0.56
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
anion of 2-nitro-1-phenylethan-1-one (in DMSO)
C8H6NO3 *
DMSO

N  Param.: 13.91

sN Param.: 0.76
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
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
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
anion of ethyl 2-nitroacetate (in DMSO)
C4H6NO4 *
DMSO

N  Param.: 15.24

sN Param.: 0.74
*** Chem. Eur. J. 2015, 21, 875-884
10.1002/chem.201404500
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate
C15H12BF6LiO2S *
MeCN

N  Param.: 11.23

sN Param.: 0.77
*** Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
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
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
(1H-inden-1-yl)trimethylstannane (in CH2Cl2)
C12H16Sn *
dichloromethane

N  Param.: 6.68

sN Param.: 0.81
*** Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
(1H-inden-1-yl)trimethylsilane (in CH2Cl2)
C12H16Si *
dichloromethane

N  Param.: -0.10

sN Param.: 1.05
*** Angew. Chem. Int. Ed. 2015, 54, 12497-12500
10.1002/anie.201501385
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C20H23BF3LiO2 *
MeCN

N  Param.: 7.15

sN Param.: 0.77
*** Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C21H25BF3LiO2 *
MeCN

N  Param.: 8.56

sN Param.: 0.76
*** Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C15H21BF3LiO2 *
MeCN

N  Param.: 7.68

sN Param.: 0.78
*** Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)
C20H23BF3LiO2 *
MeCN

N  Param.: 11.29

sN Param.: 0.76
*** Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO)
C7H11O3 *
DMSO

N  Param.: 19.58

sN Param.: 0.73
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)
C8H11O3 *
DMSO

N  Param.: 18.63

sN Param.: 0.82
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)
C9H13O3 *
DMSO

N  Param.: 18.32

sN Param.: 0.84
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide
C10H15O3 *
DMSO

N  Param.: 19.53

sN Param.: 0.83
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO)
C11H17O3 *
DMSO

N  Param.: 20.02

sN Param.: 0.76
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO)
C15H25O3 *
DMSO

N  Param.: 20.60

sN Param.: 0.63
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)
C6H7O3 *
DMSO

N  Param.: 14.46

sN Param.: 0.91
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)
C7H9O3 *
DMSO

N  Param.: 17.00

sN Param.: 0.74
*** Eur. J. Org. Chem. 2015, , 7594-7601
10.1002/ejoc.201501107
anion of diethyl 2-(isopropyl)malonate (in DMSO)
C10H17O4 *
DMSO

N  Param.: 18.74

sN Param.: 0.71
*** Eur. J. Org. Chem. 2016, , 1841-1848
10.1002/ejoc.201600107
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