Mayr's Database of Reactivity Parameters

Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles

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Name Solvent Reactivity
Parameters 		Classification Reference
(title or year)
methylenecycloheptane
C8H14 *
 dichloromethane

N  Param.: 2.24

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
methylenecyclodecane
C11H20 *
 dichloromethane

N  Param.: 2.82

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
methylenecycloundecane
C12H22 *
 dichloromethane

N  Param.: 2.33

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
methylenecyclopentadecane
C16H30 *
 dichloromethane

N  Param.: 1.69

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-(bis(trimethylsiloxy)amino)propene
C9H23NO2Si2 *
 dichloromethane

N  Param.: 4.76

sN Param.: 0.86		 *** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
(bis(trimethylsiloxy)amino)styrene
C14H25NO2Si2 *
 dichloromethane

N  Param.: 4.80

sN Param.: 0.86		 * J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
2-(bis(tert-butyldimethylsiloxy)amino)propene
C15H35NO2Si2 *
 dichloromethane

N  Param.: 4.23

sN Param.: 0.93		 *** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester
C12H27NO4Si2 *
 dichloromethane

N  Param.: 3.84

sN Param.: 0.87		 *** J. Org. Chem. 2001, 66, 3196-3200
10.1021/jo0015927
propene
C3H6 *
 dichloromethane

N  Param.: -2.41

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2-chloropropene
C3H5Cl *
 dichloromethane

N  Param.: -3.65

sN Param.: 1.97		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
1-hexene
C6H12 *
 dichloromethane

N  Param.: -2.77

sN Param.: 1.41		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
1-methylcyclohexene
C7H12 *
 dichloromethane

N  Param.: 0.08

sN Param.: 1.15		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methyl-but-2-ene
C5H10 *
 dichloromethane

N  Param.: 0.65

sN Param.: 1.17		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methylpropene (isobutylene)
C4H8 *
 dichloromethane

N  Param.: 1.11

sN Param.: 0.98		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
1-methyl-4-vinyl-benzene
C9H10 *
 dichloromethane

N  Param.: 1.70

sN Param.: 1.06		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-methyl-buta-1,3-diene (isoprene)
C5H8 *
 dichloromethane

N  Param.: 1.10

sN Param.: 0.98		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
allylchlorodimethylsilane
C5H11ClSi *
 dichloromethane

N  Param.: -0.57

sN Param.: 1.06		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
trimethyl(prenyl)silane
C8H18Si *
 dichloromethane

N  Param.: 0.90

sN Param.: 1.17		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(2-methylallyl)triphenylgermane
C22H22Ge *
 dichloromethane

N  Param.: 4.67

sN Param.: 0.81		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
allyl-tert.butyl-dimethylsilane
C9H20Si *
 dichloromethane

N  Param.: 1.80

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltriethylsilane
C9H20Si *
 dichloromethane

N  Param.: 1.93

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltriisopropylsilane
C12H26Si *
 dichloromethane

N  Param.: 2.04

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltri-n-butylsilane
C15H32Si *
 dichloromethane

N  Param.: 2.09

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltrihexylsilane
C21H44Si *
 dichloromethane

N  Param.: 2.11

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(Z)-but-2-enyltrimethylsilane
C7H16Si *
 dichloromethane

N  Param.: 1.69

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(E)-but-2-enyltrimethylsilane
C7H16Si *
 dichloromethane

N  Param.: 1.94

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(2,3-dimethylbut-2-enyl)triethylsilane
C12H26Si *
 dichloromethane

N  Param.: 3.15

sN Param.: 1.15		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,3,3-trimethyl-but-1-ene
C7H14 *
 dichloromethane

N  Param.: 0.06

sN Param.: 1.07		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2,3-dimethyl-but-1-ene
C6H12 *
 dichloromethane

N  Param.: 0.65

sN Param.: 1.00		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2,4,4-trimethyl-pent-1-ene
C8H16 *
 dichloromethane

N  Param.: 0.79

sN Param.: 1.07		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2-methyl-but-1-ene
C5H10 *
 dichloromethane

N  Param.: 1.00

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,4-dimethyl-penta-1,4-diene
C7H12 *
 dichloromethane

N  Param.: 0.54

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,5-dimethyl-hexa-1,5-diene
C8H14 *
 dichloromethane

N  Param.: 1.14

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,6-dimethyl-hepta-1,6-diene
C9H16 *
 dichloromethane

N  Param.: 1.69

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,7-dimethylocta-1,7-diene
C10H18 *
 dichloromethane

N  Param.: 1.58

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
tris(4-chlorophenyl)phosphane
C18H12Cl3P *
 dichloromethane

N  Param.: 12.58

sN Param.: 0.65		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tris(4-methylphenyl)phosphane
C21H21P *
 dichloromethane

N  Param.: 15.44

sN Param.: 0.64		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tris(4-methoxyphenyl)phosphane
C21H21O3P *
 dichloromethane

N  Param.: 16.17

sN Param.: 0.62		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tris(4-dimethylaminophenyl)phosphane
C24H30N3P *
 dichloromethane

N  Param.: 18.39

sN Param.: 0.64		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
triisopropylphosphane
C9H21P *
 dichloromethane

N  Param.: 13.37

sN Param.: 0.70		 * Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tricyclohexylphosphane
C18H33P *
 dichloromethane

N  Param.: 14.64

sN Param.: 0.68		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tri-n-butylphosphane
C12H27P *
 dichloromethane

N  Param.: 15.49

sN Param.: 0.69		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
triphenyl phosphite
C18H15O3P *
 dichloromethane

N  Param.: 5.51

sN Param.: 0.76		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
tributyl phosphite
C12H27O3P *
 dichloromethane

N  Param.: 10.36

sN Param.: 0.70		 *** Chem. Eur. J. 2005, 11, 917-927
10.1002/chem.200400696
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