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)
toluene
C7H8 *
 dichloromethane

N  Param.: -4.36

sN Param.: 1.77		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
2-chloropropene
C3H5Cl *
 dichloromethane

N  Param.: -3.65

sN Param.: 1.97		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
m-xylene
C8H10 *
 dichloromethane

N  Param.: -3.57

sN Param.: 2.08		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene
*
 dichloromethane

N  Param.: -3.52

sN Param.: 1.17		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
3,3,3-trifluoro-2-(trimethylsiloxy)propene
*
 dichloromethane

N  Param.: -2.94

sN Param.: 1.11		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
1-hexene
C6H12 *
 dichloromethane

N  Param.: -2.77

sN Param.: 1.41		 ***** 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
(Z)-but-2-ene
C4H8 *
 dichloromethane

N  Param.: -2.44

sN Param.: 1.09		 ** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
propene
C3H6 *
 dichloromethane

N  Param.: -2.41

sN Param.: 1.00		 * 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
2-(trimethylsilyl)propene
C6H14Si *
 dichloromethane

N  Param.: -1.46

sN Param.: 1.05		 *** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
dimethyl diazomalonate
C5H6N2O4 *
 dichloromethane

N  Param.: -1.24

sN Param.: 0.81		 *** J. Am. Chem. Soc. 2023, 145, 7416-7434
10.1021/jacs.2c13872
anisole
C7H8O *
 dichloromethane

N  Param.: -1.18

sN Param.: 1.20		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
alpha-(trimethylsilyl)styrene
C11H16Si *
 dichloromethane

N  Param.: -1.13

sN Param.: 1.46		 *** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
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
(Z)-phenylpropene
C9H10 *
 dichloromethane

N  Param.: -1.07

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
tetramethylethylene
C6H12 *
 dichloromethane

N  Param.: -1.00

sN Param.: 1.40		 *** 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
2-(trimethylsilyl)thiophene
C7H12SSi *
 dichloromethane

N  Param.: -0.80

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
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
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)
C9H17BO2 *
 dichloromethane

N  Param.: -0.64

sN Param.: 1.10		 *** J. Am. Chem. Soc. 2017, 139, 15324-15327
10.1021/jacs.7b10240
allylchlorodimethylsilane
C5H11ClSi *
 dichloromethane

N  Param.: -0.57

sN Param.: 1.06		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(2-methylallyl)trichlorosilane
C4H7Cl3Si *
 dichloromethane

N  Param.: -0.57

sN Param.: 0.95		 * 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
(E)-propenylbenzene
C9H10 *
 dichloromethane

N  Param.: -0.49

sN Param.: 1.18		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
methylenecyclopropane
C4H6 *
 dichloromethane

N  Param.: -0.47

sN Param.: 0.90		 * 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
beta-(trimethylsilyl)styrene
C11H16Si *
 dichloromethane

N  Param.: -0.43

sN Param.: 1.06		 *** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
diethyl diazomalonate
C7H10N2O4 *
 dichloromethane

N  Param.: -0.35

sN Param.: 0.93		 ** Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
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
2-(pentamethyldisilyl)propene
C8H20Si2 *
 dichloromethane

N  Param.: -0.26

sN Param.: 0.95		 *** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
norbornene
C7H10 *
 dichloromethane

N  Param.: -0.25

sN Param.: 1.09		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
allyltriphenylsilane
C21H20Si *
 dichloromethane

N  Param.: -0.13

sN Param.: 1.21		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(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
phenylacetylene
C8H6 *
 dichloromethane

N  Param.: -0.04

sN Param.: 0.77		 *** Angew. Chem. Int. Ed. 2014, 53, 4968-4971
10.1002/anie.201402055
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
cyclohepta-1,3-diene
C7H10 *
 dichloromethane

N  Param.: 0.06

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
1-methylcyclohexene
C7H12 *
 dichloromethane

N  Param.: 0.08

sN Param.: 1.15		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
3-methylanisole
C8H10O *
 dichloromethane

N  Param.: 0.13

sN Param.: 1.27		 *** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
2-diazoindandione
C9H4N2O2 *
 dichloromethane

N  Param.: 0.16

sN Param.: 0.86		 *** Eur. J. Org. Chem. 2023, 26, e202300005
10.1002/ejoc.202300005
(2-methylallyl)benzene
C10H12 *
 dichloromethane

N  Param.: 0.25

sN Param.: 1.00		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
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
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-(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
alpha-(pentamethyldisilyl)styrene
C13H22Si2 *
 dichloromethane

N  Param.: 0.61

sN Param.: 1.01		 *** Chem. Eur. J. 2014, 20, 1103-1110
10.1002/chem.201303215
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
2,3-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
(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
cyclohexa-1,3-diene
C6H8 *
 dichloromethane

N  Param.: 0.67

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(1S)-(-)-alpha-pinene
C10H16 *
 dichloromethane

N  Param.: 0.68

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
2,4,6-trimethylstyrene
C11H14 *
 dichloromethane

N  Param.: 0.68

sN Param.: 1.09		 *** Macromolecules 2005, 38, 33-40
10.1021/ma048389o
styrene
C8H8 *
 dichloromethane

N  Param.: 0.78

sN Param.: 0.95		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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-pent-1-ene
*
 dichloromethane

N  Param.: 0.84

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-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-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
2-methylpropene (isobutylene)
C4H8 *
 dichloromethane

N  Param.: 1.11

sN Param.: 0.98		 ***** J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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
methylenecyclohexane
C7H12 *
 dichloromethane

N  Param.: 1.16

sN Param.: 1.04		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
(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
1-methylcyclopentene
C6H10 *
 dichloromethane

N  Param.: 1.18

sN Param.: 1.17		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
allyltriphenylgermane
C21H20Ge *
 dichloromethane

N  Param.: 1.20

sN Param.: 0.90		 * 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-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
2-methylthiophene
C5H6S *
 dichloromethane

N  Param.: 1.35

sN Param.: 0.99		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
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
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene
*
 dichloromethane

N  Param.: 1.47

sN Param.: 0.89		 *** Org. Lett. 2012, 14, 3990-3993
10.1021/ol301766w
(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
methylenecyclododecane
C13H24 *
 dichloromethane

N  Param.: 1.52

sN Param.: 0.90		 * 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
3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran
C9H16O4 *
 dichloromethane

N  Param.: 1.53

sN Param.: 1.38		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
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
methylenecyclobutane
C5H8 *
 dichloromethane

N  Param.: 1.65

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyltrimethylsilane
C6H14Si *
 dichloromethane

N  Param.: 1.68

sN Param.: 1.00		 ***** J. Am. Chem. Soc. 2012, 134, 13902-13911
10.1021/ja306522b
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
methylenecyclopentadecane
C16H30 *
 dichloromethane

N  Param.: 1.69

sN Param.: 0.90		 * 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
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
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-(acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate
C12H16O7 *
 dichloromethane

N  Param.: 1.72

sN Param.: 1.24		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran
C27H28O4 *
 dichloromethane

N  Param.: 1.75

sN Param.: 1.37		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
3-(trimethylsilyl)cyclopentene
C8H16Si *
 dichloromethane

N  Param.: 1.77

sN Param.: 1.10		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
allyl-tert.butyl-dimethylsilane
C9H20Si *
 dichloromethane

N  Param.: 1.80

sN Param.: 0.95		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
(5-methyl-furan-2-yl) MIDA boronate
*
 MeCN

N  Param.: 1.84

sN Param.: 1.26		 ** Chem. Sci. 2012, 3, 878-882
10.1039/c2sc00883a
8-(benzyloxy)-2,2-di-tert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline
C21H32O4Si *
 dichloromethane

N  Param.: 1.85

sN Param.: 1.28		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran
C27H28O4 *
 dichloromethane

N  Param.: 1.89

sN Param.: 1.27		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
allyltriethylsilane
C9H20Si *
 dichloromethane

N  Param.: 1.93

sN Param.: 0.95		 * 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
8-(benzyloxy)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine
C20H20O4 *
 dichloromethane

N  Param.: 1.94

sN Param.: 1.24		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
allyltris(trimethylsilyl)silane
*
 dichloromethane

N  Param.: 1.95

sN Param.: 0.98		 *** Org. Lett. 2010, 12, 5206-5209
10.1021/ol102220e
2-((TBDMSO-methyl)-3,4-bis(TBDMSO)-3,4-dihydro-2H-pyran
C24H52O4Si3 *
 dichloromethane

N  Param.: 1.97

sN Param.: 1.20		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
3-(trihexylsilyl)cyclopentene
C23H46Si *
 dichloromethane

N  Param.: 1.98

sN Param.: 1.10		 * 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
3,4-bis(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran
C20H22O3 *
 dichloromethane

N  Param.: 2.04

sN Param.: 1.20		 *** Angew. Chem. Int. Ed. 2026, 65, e24329
10.1002/anie.202524329
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