Mayr's Database of Reactivity Parameters

C-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
Z-3-(trimethylsiloxy)pent-2-ene
C8H18OSi*
dichloromethane

N  Param.: 5.58

sN Param.: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
trimethyl(prenyl)silane
C8H18Si*
dichloromethane

N  Param.: 0.90

sN Param.: 1.17
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
toluene
C7H8*
dichloromethane

N  Param.: -4.36

sN Param.: 1.77
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
thiophene
C4H4S*
dichloromethane

N  Param.: -1.01

sN Param.: 1.10
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
tetramethylethylene
C6H12*
dichloromethane

N  Param.: -1.00

sN Param.: 1.40
***Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
tetrakis(5-methyl-furan-2-yl)borate
*
MeCN

N  Param.: 9.09

sN Param.: 1.12
***Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
tert-butyl isocyanide
C5H9N*
dichloromethane

N  Param.: 5.47

sN Param.: 0.77
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
tert-butyl indole-1-carboxylate
C13H15NO2*
MeCN

N  Param.: 1.68

sN Param.: 1.26
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
styrene
C8H8*
dichloromethane

N  Param.: 0.78

sN Param.: 0.95
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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
pyrrole
C4H5N*
dichloromethane

N  Param.: 4.63

sN Param.: 1.00
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
propene
C3H6*
dichloromethane

N  Param.: -2.41

sN Param.: 1.00
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
prenyl-tributylstannane
C17H36Sn*
dichloromethane

N  Param.: 4.74

sN Param.: 1.15
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
potassium trifluoro(furan-3-yl)borate
C4H3BF3KO*
MeCN

N  Param.: 6.83

sN Param.: 0.93
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(3-methoxy-thiophen-2-yl)borate
C5H5BF3KOS*
MeCN

N  Param.: 7.32

sN Param.: 0.90
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-5-yl)borate
C9H8BF3KN*
MeCN

N  Param.: 8.77

sN Param.: 1.09
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium trifluoro(1-methyl-1H-indol-2-yl)borate
C9H8BF3KN*
MeCN

N  Param.: 9.55

sN Param.: 1.16
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
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
potassium allyltrifluoroborate (in MeCN)
C3H5BF3K*
MeCN

N  Param.: 5.29

sN Param.: 0.87
**J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240
potassium (1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-yl)trifluoroborate
C14H16BF3KNO3*
MeCN

N  Param.: 7.10

sN Param.: 1.18
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-3-yl)trifluoroborate
C13H14BF3KNO2*
MeCN

N  Param.: 4.06

sN Param.: 0.79
**J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
potassium (1-(tert-butoxycarbonyl)-1H-indol-2-yl)trifluoroborate
C13H14BF3KNO2*
MeCN

N  Param.: 6.46

sN Param.: 0.96
***J. Am. Chem. Soc. 2013, 135, 6317-6324
10.1021/ja4017655
phenyldiazomethane
C7H6N2*
dichloromethane

N  Param.: 9.35

sN Param.: 0.83
***Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
phenylacetylene
C8H6*
dichloromethane

N  Param.: -0.04

sN Param.: 0.77
***Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
Ph3P=CH-COPh
*
dichloromethane

N  Param.: 9.54

sN Param.: 0.97
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 12.21

sN Param.: 0.62
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CO2Et
*
dichloromethane

N  Param.: 12.79

sN Param.: 0.77
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph3P=CH-CN
*
dichloromethane

N  Param.: 12.29

sN Param.: 0.75
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
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
Ph3P=C(CH3)-CO2Et
*
dichloromethane

N  Param.: 13.09

sN Param.: 0.73
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CO2Et (in DMSO)
*
DMSO

N  Param.: 19.20

sN Param.: 0.69
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
Ph2P(O)CH(-)CN (in DMSO)
*
DMSO

N  Param.: 18.69

sN Param.: 0.72
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
p-tosylmethyl isocyanide (TosMIC)
C9H9NO2S*
dichloromethane

N  Param.: 3.50

sN Param.: 0.76
***Angew. Chem. Int. Ed. 2007, 46, 3563-3566
10.1002/anie.200605205
norbornene
C7H10*
dichloromethane

N  Param.: -0.25

sN Param.: 1.09
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
N-vinylcarbazole
C14H11N*
dichloromethane

N  Param.: 5.02

sN Param.: 0.94
**Macromolecules 2002, 35, 5454-5458
10.1021/ma020306l
N-methylpyrrole
C5H7N*
dichloromethane

N  Param.: 5.85

sN Param.: 1.03
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-methylindole
C9H9N*
dichloromethane

N  Param.: 5.75

sN Param.: 1.23
***J. Org. Chem. 2006, 71, 9088-9095
10.1021/jo0614339
N-methylenepyrrolidin-1-amine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 7.84

sN Param.: 0.89
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
n-butyl vinyl ether
*
dichloromethane

N  Param.: 3.76

sN Param.: 0.91
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
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
N-(triisopropylsilyl)pyrrole
C13H25NSi*
dichloromethane

N  Param.: 3.12

sN Param.: 0.93
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
N-(cyclopent-1-en-1-yl)acetamide
C7H11NO*
MeCN

N  Param.: 7.06

sN Param.: 0.87
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(cyclohex-1-en-1-yl)acetamide
C8H13NO*
MeCN

N  Param.: 5.64

sN Param.: 0.79
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(3,4-dihydronaphthalen-1-yl)acetamide
C12H13NO*
MeCN

N  Param.: 4.91

sN Param.: 0.87
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(3,3-dimethylbut-1-en-2-yl)acetamide
C8H15NO*
MeCN

N  Param.: 4.61

sN Param.: 0.98
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-phenylvinyl)benzamide
C15H13NO*
MeCN

N  Param.: 5.44

sN Param.: 1.00
*Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-phenylvinyl)acetamide
C10H11NO*
MeCN

N  Param.: 5.73

sN Param.: 0.97
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(p-tolyl)vinyl)acetamide
C11H13NO*
MeCN

N  Param.: 6.57

sN Param.: 0.91
**Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(naphthalen-2-yl)vinyl)acetamide
C14H13NO*
MeCN

N  Param.: 6.28

sN Param.: 0.95
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(4-methoxyphenyl)vinyl)acetamide
C11H13NO2*
MeCN

N  Param.: 7.06

sN Param.: 0.85
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N-(1-(4-chlorophenyl)vinyl)acetamide
C10H10ClNO*
MeCN

N  Param.: 5.60

sN Param.: 1.00
***Chem. Eur. J. 2012, 18, 5732-5740
10.1002/chem.201103519
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2)
*
dichloromethane

N  Param.: 7.98

sN Param.: 0.71
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
morpholinoisobutylene
C8H15NO*
dichloromethane

N  Param.: 10.04

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
methylenecycloundecane
C12H22*
dichloromethane

N  Param.: 2.33

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclopropane
C4H6*
dichloromethane

N  Param.: -0.47

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclopentane
C6H10*
dichloromethane

N  Param.: 2.82

sN Param.: 0.90
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
methylenecyclopentadecane
C16H30*
dichloromethane

N  Param.: 1.69

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclooctane
C9H16*
dichloromethane

N  Param.: 3.16

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclononane
C10H18*
dichloromethane

N  Param.: 2.57

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclohexane
C7H12*
dichloromethane

N  Param.: 1.16

sN Param.: 1.04
*****J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
methylenecycloheptane
C8H14*
dichloromethane

N  Param.: 2.24

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclododecane
C13H24*
dichloromethane

N  Param.: 1.52

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclodecane
C11H20*
dichloromethane

N  Param.: 2.82

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecyclobutane
C5H8*
dichloromethane

N  Param.: 1.65

sN Param.: 0.90
*Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methyl (cyclohexen-1-yl)prolinate (in MeCN)
*
MeCN

N  Param.: 14.96

sN Param.: 0.68
***Angew. Chem. Int. Ed. 2010, 49, 9526-9529
10.1002/anie.201004344
methoxybis(phenylsulfonyl)methanide (in DMSO)
C14H13O5S2*
DMSO

N  Param.: 17.29

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2016, 55, 12845-12848
10.1002/anie.201605616
MeSO2-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 18.00

sN Param.: 0.66
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
MeSO-CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 20.61

sN Param.: 0.64
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
MeO-Breslow 1e
*
THF

N  Param.: 15.65

sN Param.: 0.52
***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 1b
*
THF

N  Param.: 10.45

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

N  Param.: 14.77

sN Param.: 0.80
***Angew. Chem. Int. Ed. 2012, 51, 10408-10412
10.1002/anie.201204524
Meldrum's acid iodonium ylide (in CH2Cl2)
*
dichloromethane

N  Param.: 4.36

sN Param.: 1.06
***J. Am. Chem. Soc. 2016, 138, 10304-10313
10.1021/jacs.6b05768
Me2S=CH-CO2Et (in DMSO)
*
DMSO

N  Param.: 15.85

sN Param.: 0.61
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
Me2S=CH-CN (in DMSO)
*
DMSO

N  Param.: 16.23

sN Param.: 0.60
***Chem. Eur. J. 2010, 16, 8610-8614
10.1002/chem.201001455
Me2S=CH(p-NO2-C6H4) (in DMSO)
*
DMSO

N  Param.: 18.42

sN Param.: 0.65
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
Me2S=CH(4-CN-C6H4) (in DMSO)
*
DMSO

N  Param.: 21.07

sN Param.: 0.68
***J. Am. Chem. Soc. 2010, 132, 17894-17900
10.1021/ja1084749
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
m-xylene
C8H10*
dichloromethane

N  Param.: -3.57

sN Param.: 2.08
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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
lithium bis(5-methylthiophen-2-yl)pinacolborate
C16H22BLiO2S2*
MeCN

N  Param.: 7.67

sN Param.: 0.87
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
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.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C20H26BLiO2*
MeCN

N  Param.: 10.97

sN Param.: 0.63
**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-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C16H23BF3LiO2*
MeCN

N  Param.: 6.63

sN Param.: 0.75
*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 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C16H21BF3LiO2*
MeCN

N  Param.: 7.72

sN Param.: 0.75
*Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C19H24BLiO2*
MeCN

N  Param.: 8.92

sN Param.: 0.70
**Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
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 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C21H22BF6LiO2*
MeCN

N  Param.: 6.30

sN Param.: 0.78
**Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C15H22BLiO2*
MeCN

N  Param.: 11.20

sN Param.: 0.64
*J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C17H20BF6LiO2*
MeCN

N  Param.: 8.71

sN Param.: 0.80
***J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)
C22H24BF6LiO2*
MeCN

N  Param.: 7.46

sN Param.: 0.76
**Org. Lett. 2015, 17, 2614-2617
10.1021/acs.orglett.[...]
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)
C18H22BF6LiO2*
MeCN

N  Param.: 9.49

sN Param.: 0.82
***J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate
C17H22BLiO2S*
MeCN

N  Param.: 7.24

sN Param.: 0.83
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate
C18H24BLiO2S*
MeCN

N  Param.: 6.98

sN Param.: 0.93
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate
C18H24BLiO3S*
MeCN

N  Param.: 7.51

sN Param.: 0.87
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate
C17H21BClLiO2S*
MeCN

N  Param.: 6.77

sN Param.: 0.88
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562