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)
furan
C4H4O *
 dichloromethane

N  Param.: 1.33

sN Param.: 1.29		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2-(trimethylsilyl)furan
C7H12OSi *
 dichloromethane

N  Param.: 2.16

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(triethylsilyl)furan
C10H18OSi *
 dichloromethane

N  Param.: 2.20

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylsilyl)furan
C16H30OSi *
 dichloromethane

N  Param.: 2.37

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
thiophene
C4H4S *
 dichloromethane

N  Param.: -1.01

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(trimethylsilyl)thiophene
C7H12SSi *
 dichloromethane

N  Param.: -0.80

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylstannyl)furan
C16H30OSn *
 dichloromethane

N  Param.: 3.63

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(tributylstannyl)thiophene
C16H30SSn *
 dichloromethane

N  Param.: 1.53

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
buta-1,3-diene
C4H6 *
 dichloromethane

N  Param.: -0.87

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(Z)-penta-1,3-diene
C5H8 *
 dichloromethane

N  Param.: 0.66

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(E,E)-hexa-2,4-diene
C6H10 *
 dichloromethane

N  Param.: 1.17

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,3-dimethyl-buta-1,3-diene
C6H10 *
 dichloromethane

N  Param.: 1.17

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(E)-penta-1,3-diene
C5H8 *
 dichloromethane

N  Param.: 1.49

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
4-methyl-penta-1,3-diene
C6H10 *
 dichloromethane

N  Param.: 2.60

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(E)-2-methyl-penta-1,3-diene
C6H10 *
 dichloromethane

N  Param.: 3.09

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-ethinylcyclohexenyl-Co2(CO)6
*
 dichloromethane

N  Param.: -0.44

sN Param.: 1.06		 *** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6
*
 dichloromethane

N  Param.: -1.11

sN Param.: 0.92		 *** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
cyclohepta-1,3,5-trienyl-Fe(CO)3
*
 dichloromethane

N  Param.: 3.42

sN Param.: 0.94		 *** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)
*
 dichloromethane

N  Param.: -0.76

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-phenyl-4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6
*
 dichloromethane

N  Param.: 1.33

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
diazomethane
CH2N2 *
 dichloromethane

N  Param.: 10.48

sN Param.: 0.78		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
phenyldiazomethane
C7H6N2 *
 dichloromethane

N  Param.: 9.35

sN Param.: 0.83		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
(trimethylsilyl)diazomethane
C4H10N2Si *
 dichloromethane

N  Param.: 8.97

sN Param.: 0.75		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
diphenyldiazomethane
C13H10N2 *
 dichloromethane

N  Param.: 5.29

sN Param.: 0.92		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
ethyl diazoacetate
C4H6N2O2 *
 dichloromethane

N  Param.: 4.91

sN Param.: 0.95		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
diazoacetone
C3H4N2O *
 dichloromethane

N  Param.: 3.96

sN Param.: 0.91		 *** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
diethyl diazomalonate
C7H10N2O4 *
 dichloromethane

N  Param.: -0.35

sN Param.: 0.93		 ** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
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
cyclohexa-1,3-diene
C6H8 *
 dichloromethane

N  Param.: 0.67

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
cyclohepta-1,3-diene
C7H10 *
 dichloromethane

N  Param.: 0.06

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
cycloocta-1,3-diene
C8H12 *
 dichloromethane

N  Param.: -0.50

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
cyclopentadiene
C5H6 *
 dichloromethane

N  Param.: 2.30

sN Param.: 1.06		 *** Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3,3-dimethyl-2-(trimethylsiloxy)buten
C9H20OSi *
 dichloromethane

N  Param.: 3.78

sN Param.: 0.79		 ** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-methoxy-2-methyl-1-(trimethylsiloxy)propene
C8H18O2Si *
 dichloromethane

N  Param.: 9.00

sN Param.: 0.98		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methyl-1-(trimethylsiloxy)propen
C7H16OSi *
 dichloromethane

N  Param.: 3.94

sN Param.: 1.00		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(Z)-1-(triisopropylsiloxy)propen
C12H26OSi *
 dichloromethane

N  Param.: 3.87

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1,2-bis(trimethylsiloxy)cyclohexene
C12H26O2Si2 *
 dichloromethane

N  Param.: 4.46

sN Param.: 1.15		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(trimethylsiloxy)buta-1,3-diene
C7H14OSi *
 dichloromethane

N  Param.: 4.83

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)buta-1,3-diene
C7H14OSi *
 dichloromethane

N  Param.: 4.60

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)cycloheptene
C10H20OSi *
 dichloromethane

N  Param.: 6.62

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-(trimethylsiloxy)cyclooctene
C11H22OSi *
 dichloromethane

N  Param.: 6.77

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
2-(trimethylsiloxy)furan
C7H12O2Si *
 dichloromethane

N  Param.: 7.22

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3-(trimethylsilyl)cyclopentene
C8H16Si *
 dichloromethane

N  Param.: 1.77

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
3-(trihexylsilyl)cyclopentene
C23H46Si *
 dichloromethane

N  Param.: 1.98

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(2-methylallyl)trichlorosilane
C4H7Cl3Si *
 dichloromethane

N  Param.: -0.57

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltriphenylgermane
C21H20Ge *
 dichloromethane

N  Param.: 1.20

sN Param.: 0.90		 * 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
(2-methylallyl)triphenylstannane
C22H22Sn *
 dichloromethane

N  Param.: 5.13

sN Param.: 0.90		 * 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
(2-methylallyl)benzene
C10H12 *
 dichloromethane

N  Param.: 0.25

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
alpha-methylstyrene
C9H10 *
 dichloromethane

N  Param.: 2.35

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-cyclopropylpropene
C6H10 *
 dichloromethane

N  Param.: 2.60

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(Z)-phenylpropene
C9H10 *
 dichloromethane

N  Param.: -1.07

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
cyclopentene
C5H8 *
 dichloromethane

N  Param.: -1.55

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
norbornene
C7H10 *
 dichloromethane

N  Param.: -0.25

sN Param.: 1.09		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(1S)-(-)-alpha-pinene
C10H16 *
 dichloromethane

N  Param.: 0.68

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-methylcyclopentene
C6H10 *
 dichloromethane

N  Param.: 1.18

sN Param.: 1.17		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(E)-but-2-ene
C4H8 *
 dichloromethane

N  Param.: -2.45

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
ethyl-vinylether
C4H8O *
 dichloromethane

N  Param.: 3.92

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
isobutylenyl-ethylether
C6H12O *
 dichloromethane

N  Param.: 4.23

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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 DMSO)
C8H13O4- *
 DMSO

N  Param.: 21.13

sN Param.: 0.68		 *** 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 DMSO)
C6H9O2- *
 DMSO

N  Param.: 18.38

sN Param.: 0.72		 *** 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
1,1-diethoxyethene
C6H12O2 *
 dichloromethane

N  Param.: 9.81

sN Param.: 0.81		 *** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1-butoxy-1-(trimethylsiloxy)ethene
C9H20O2Si *
 dichloromethane

N  Param.: 10.21

sN Param.: 0.82		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1-butoxy-1-(t-butyl-dimethylsiloxy)ethene
C12H26O2Si *
 dichloromethane

N  Param.: 10.32

sN Param.: 0.79		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
1,1-bis(trimethylsiloxy)propene
C9H22O2Si2 *
 dichloromethane

N  Param.: 10.38

sN Param.: 0.87		 **** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
4-methyl-5-(trimethylsiloxy)-2,3-dihydrofuran
C8H16O2Si *
 dichloromethane

N  Param.: 11.50

sN Param.: 0.91		 *** Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
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 nitromethane (in DMSO)
CH2NO2- *
 DMSO

N  Param.: 20.71

sN Param.: 0.60		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
anion of 2-nitropropane (in DMSO)
C3H6NO2- *
 DMSO

N  Param.: 20.61

sN Param.: 0.69		 *** 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 phenylnitromethane (in DMSO)
C7H6NO2- *
 DMSO

N  Param.: 18.29

sN Param.: 0.71		 *** 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 p-tolylnitromethane (in DMSO)
C8H8NO2- *
 DMSO

N  Param.: 18.31

sN Param.: 0.76		 *** 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 (4-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4- *
 DMSO

N  Param.: 16.29

sN Param.: 0.75		 *** 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 (3-nitrophenyl)nitromethane (in DMSO)
C7H5N2O4- *
 DMSO

N  Param.: 18.06

sN Param.: 0.71		 *** 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
anion of (4-cyanophenyl)nitromethane (in DMSO)
C8H5N2O2- *
 DMSO

N  Param.: 16.96

sN Param.: 0.73		 *** J. Org. Chem. 2004, 69, 7565-7576
10.1021/jo048773j
cyanide (in MeCN)
CN- *
 MeCN

N  Param.: 16.27

sN Param.: 0.70		 *** Angew. Chem. Int. Ed. 2005, 44, 142-145
10.1002/anie.200461640
2,4,6-trimethylstyrene
C11H14 *
 dichloromethane

N  Param.: 0.68

sN Param.: 1.09		 *** Macromolecules 2005, 38, 33-40
10.1021/ma048389o
5-(tris(pentafluorophenyl)siloxy)-2,3-dihydrofuran
C22H5F15O2Si *
 dichloromethane

N  Param.: 8.16

sN Param.: 0.67		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
5-(triphenylsiloxy)-2,3-dihydrofuran
C22H20O2Si *
 dichloromethane

N  Param.: 11.28

sN Param.: 0.91		 *** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(triphenylsiloxy)cyclopentene
C23H22OSi *
 dichloromethane

N  Param.: 5.76

sN Param.: 1.02		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2,3-dihydrofuran
C4H6O *
 dichloromethane

N  Param.: 4.37

sN Param.: 0.90		 **** Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
2-(tris(pentafluorophenyl)siloxy)-propene
C21H5F15OSi *
 dichloromethane

N  Param.: 0.58

sN Param.: 0.91		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706
1-(tris(pentafluorophenyl)siloxy)-cyclopentene
C23H7F15OSi *
 dichloromethane

N  Param.: 1.38

sN Param.: 0.93		 * Eur. J. Org. Chem. 2005, , 1760-1764
10.1002/ejoc.200400706