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)
(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
(3-chlorobenzyl)dimethylsilane
C9H13ClSi *
 dichloromethane

N  Param.: 1.30

sN Param.: 0.75		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
tetraisobutylstannane
*
 dichloromethane

N  Param.: 1.35

sN Param.: 1.10		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
50% water/50% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 1.50

sN Param.: 1.03		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
HMn(CO)5
*
 dichloromethane

N  Param.: 1.50

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
methylenecyclododecane
C13H24 *
 dichloromethane

N  Param.: 1.52

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

N  Param.: 1.52

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
HCr(CO)3Cp*
*
 dichloromethane

N  Param.: 1.60

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
methylenecyclobutane
C5H8 *
 dichloromethane

N  Param.: 1.65

sN Param.: 0.90		 * Acc. Chem. Res. 2003, 36, 66-77
10.1021/ar020094c
30% water/70% HFIP (w/w)
*
 water-HFIP mix

N  Param.: 1.65

sN Param.: 0.96		 *** J. Phys. Org. Chem. 2013, 26, 59-63
10.1002/poc.3064
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
HW(CO)3Cp
*
 dichloromethane

N  Param.: 1.70

sN Param.: 0.80		 - Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
1,4-dimethylcyclohexa-1,4-diene (in CH2Cl2)
C8H12 *
 dichloromethane

N  Param.: 1.88

sN Param.: 0.96		 ** J. Am. Chem. Soc. 2014, 136, 13863-13873
10.1021/ja507598y
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
methyl(phenyl)silane
C7H10Si *
 dichloromethane

N  Param.: 2.13

sN Param.: 0.73		 * Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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