Mayr's Database of Reactivity Parameters

Nucleophiles

2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 Found 1357 molecules, displaying page 6 of 14 Results per page 10|50|100|all
Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one
C23H26N2O*
MeCN

N  Param.: 7.92

sN Param.: 1.07
***Angew. Chem. Int. Ed. 2012, 51, 5739-5742
10.1002/anie.201201240
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylbut-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)
C19H28N2S*
MeCN

N  Param.: 7.92

sN Param.: 0.73
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
borane-trimethylamine-complex
*
dichloromethane

N  Param.: 7.97

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
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
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)
C22H26N2S *
dichloromethane

N  Param.: 7.99

sN Param.: 0.98
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
chloride (in hexafluoroisopropanol)
Cl*
HFIP

N  Param.: 8.00

sN Param.: 0.60
*J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
HRu(CO)2Cp*
*
dichloromethane

N  Param.: 8.00

sN Param.: 0.80
-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2,5-dimethylpyrrole
C6H9N*
MeCN

N  Param.: 8.01

sN Param.: 0.96
***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate
C19H27BLiNO2S*
MeCN

N  Param.: 8.02

sN Param.: 0.89
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
fluoride (in 10 % aq MeCN)
F*
water-MeCN mix

N  Param.: 8.05

sN Param.: 0.64
***J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
N-(p-anisyl)-1,4-dihydronicotineamide
C13H14N2O2*
dichloromethane

N  Param.: 8.11

sN Param.: 0.92
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)
C17H24N2S*
MeCN

N  Param.: 8.12

sN Param.: 0.88
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate
C18H21BF3LiO3*
MeCN

N  Param.: 8.13

sN Param.: 0.85
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in CH2Cl2)
C17H24N2S *
dichloromethane

N  Param.: 8.13

sN Param.: 0.97
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
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
HFe(CO)2Cp*
*
dichloromethane

N  Param.: 8.20

sN Param.: 0.69
-Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1-phenoxy-1-(trimethylsiloxy)ethene
C11H16O2Si*
dichloromethane

N  Param.: 8.23

sN Param.: 0.81
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
(E)-4-(benzylthio)-2,2,5,5-tetramethyl-1-styryl-2,5-dihydro-1H-imidazole (in MeCN)
C22H26N2S*
MeCN

N  Param.: 8.30

sN Param.: 0.84
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
2-(4-nitrophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 8.36

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2-methylallyl)dicarbonyl(cyclopentadienyl)iron(II)
*
dichloromethane

N  Param.: 8.45

sN Param.: 0.83
***Helv. Chim. Acta 2005, 88, 1754-1768
10.1002/hlca.200590137
ethyl (E)-3-(N-morpholino)acrylate
C9H15NO3*
dichloromethane

N  Param.: 8.52

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
borane-N,N-diethylaniline-complex
*
dichloromethane

N  Param.: 8.53

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1-methyl uracil anion (in water)
*
water

N  Param.: 8.54

sN Param.: 0.77
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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.[...]
tris(2-methylphenyl)phosphane
C21H21P*
dichloromethane

N  Param.: 8.56

sN Param.: 0.70
-Chem. Eur. J. 2017, 23, 7422-7427
10.1002/chem.201701080
Danishefskys diene
C8H16O2Si*
dichloromethane

N  Param.: 8.57

sN Param.: 0.84
*****J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
N-methyl-1-phenylmethanimine (in CH2Cl2)
C8H9N*
dichloromethane

N  Param.: 8.60

sN Param.: 0.77
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
N-benzyl-1,4-dihydronicotineamide
C13H14N2O*
dichloromethane

N  Param.: 8.67

sN Param.: 0.82
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
1,2,5-trimethylpyrrole
C7H11N*
MeCN

N  Param.: 8.69

sN Param.: 1.07
***Eur. J. Org. Chem. 2008, , 2369-2374
10.1002/ejoc.200800092
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
2-(4-(trifluoromethyl)phenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 8.74

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one
C16H18N2O2*
MeCN

N  Param.: 8.76

sN Param.: 0.89
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
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
(E)-4-(1,2-diphenylvinyl)morpholine (in MeCN)
*
MeCN

N  Param.: 8.78

sN Param.: 0.83
***Chem. Eur. J. 2018, 24, 5901-5910
10.1002/chem.201705962
N-phenylcyclohexanimine (in CH2Cl2)
C12H15N*
dichloromethane

N  Param.: 8.80

sN Param.: 1.00
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
borane-N,N-diisopropylaniline-complex
*
dichloromethane

N  Param.: 8.84

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(p-bromophenyl)diazomethane
*
dichloromethane

N  Param.: 8.87

sN Param.: 0.82
***J. Am. Chem. Soc. 2018, 140, 16758-16772
10.1021/jacs.8b09995
borane-triethylamine-complex
C6H18BN*
dichloromethane

N  Param.: 8.90

sN Param.: 0.75
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
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.[...]
(trimethylsilyl)diazomethane
C4H10N2Si*
dichloromethane

N  Param.: 8.97

sN Param.: 0.75
***Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
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
Hantzsch ester
C13H19NO4*
dichloromethane

N  Param.: 9.00

sN Param.: 0.90
***Angew. Chem. Int. Ed. 2009, 48, 1958-1961
10.1002/anie.200804263
trimethyl phosphite (in 91M9AN)
C3H9O3P*
MeOH-MeCN mix

N  Param.: 9.04

sN Param.: 0.70
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
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
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
1-methoxy-2-methyl-1-(trimethylsiloxy)propene (in MeCN)
*
MeCN

N  Param.: 9.11

sN Param.: 0.88
***J. Am. Chem. Soc. 2013, 135, 6579-6587
10.1021/ja401106x
2,6-dimethylpyridine (in MeCN)
C7H9N*
MeCN

N  Param.: 9.11

sN Param.: 0.69
***Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
borane-N-ethyl-N-isopropylaniline-complex
*
dichloromethane

N  Param.: 9.12

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-tritylpyrrolidine
C23H23N*
MeCN

N  Param.: 9.16

sN Param.: 1.39
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
(E)-2-((1-(but-1-en-1-yl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
C13H21N3S*
MeCN

N  Param.: 9.23

sN Param.: 0.74
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
2-((2,2,5,5-tetramethyl-1-(prop-1-en-1-yl)-2,5-dihydro-1H-imidazol-4-yl)thio)acetonitrile (in MeCN)
C12H19N3S*
MeCN

N  Param.: 9.25

sN Param.: 0.84
***Chem. Commun. 2023, 59, 8091-8084
10.1039/d3cc01912h
2,4,6-trimethylpyridine (in CH2Cl2)
C8H11N*
dichloromethane

N  Param.: 9.34

sN Param.: 0.71
***Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
phenyldiazomethane
C7H6N2*
dichloromethane

N  Param.: 9.35

sN Param.: 0.83
***Chem. Eur. J. 2003, 9, 4068-4076
10.1002/chem.200304913
2-(3-chlorophenyl)-1,3-dimethyl-benzimidazoline (in MeCN)
*
MeCN

N  Param.: 9.38

sN Param.: 0.71
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2,4,6-trimethylpyridine (in MeCN)
C8H11N*
MeCN

N  Param.: 9.39

sN Param.: 0.60
***Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
ethyl (E)-3-(dimethylamino)acrylate
C7H13NO2*
dichloromethane

N  Param.: 9.43

sN Param.: 0.80
*Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
2-methyl-imidazole (in water)
*
water

N  Param.: 9.45

sN Param.: 0.54
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
ammonia (in water)
H3N*
water

N  Param.: 9.48

sN Param.: 0.59
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
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
N-phenylpropan-2-imine (in CH2Cl2)
C9H11N*
dichloromethane

N  Param.: 9.53

sN Param.: 0.85
***Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
Ph3P=CH-COPh
*
dichloromethane

N  Param.: 9.54

sN Param.: 0.97
***J. Am. Chem. Soc. 2009, 131, 704-714
10.1021/ja8056216
dipp Imd boronate
*
dichloromethane

N  Param.: 9.55

sN Param.: 0.81
***Org. Lett. 2012, 14, 82-85
10.1021/ol202836p
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
imidazole (in water)
*
water

N  Param.: 9.63

sN Param.: 0.57
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
(E)-4-(ethylthio)-2,2,5,5-tetramethyl-1-(3-phenylprop-1-en-1-yl)-2,5-dihydro-1H-imidazole (in MeCN)
C18H26N2S*
MeCN

N  Param.: 9.64

sN Param.: 0.70
***Chem. Eur. J. 2024, 30, e202302764
10.1002/chem.202302764
2-phenyl-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 9.72

sN Param.: 0.72
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
fluoride (in 60% aq MeCN)
F*
water-MeCN mix

N  Param.: 9.75

sN Param.: 0.63
***J. Org. Chem. 2012, 77, 3325-3335
10.1021/jo300141z
N-benzyl-1,4-dihydronicotineamide (in 50W50AN)
*
water-MeCN mix

N  Param.: 9.79

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
N-benzyl-1,4-dihydronicotineamide (in MeCN)
*
MeCN

N  Param.: 9.80

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
1,1-diethoxyethene
C6H12O2*
dichloromethane

N  Param.: 9.81

sN Param.: 0.81
***Eur. J. Org. Chem. 2004, , 2791-2796
10.1002/ejoc.200400134
2-methyl-4,5-dihydro-1,3-oxazole (in CH2Cl2)
C4H7NO*
dichloromethane

N  Param.: 9.81

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2,6-dimethylpyridine (in CH2Cl2)
C7H9N*
dichloromethane

N  Param.: 9.87

sN Param.: 0.68
***Synthesis 2017, 49, 3495-3504
10.1055/s-0036-1590504
(S)-2-(azidodiphenylmethyl)pyrrolidine
C17H18N4*
MeCN

N  Param.: 9.90

sN Param.: 1.22
***J. Am. Chem. Soc. 2020, 142, 1526-1547
10.1021/jacs.9b11877
1-methyl-imidazole (in water)
*
water

N  Param.: 9.91

sN Param.: 0.55
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
(E)-1-(1,2-diphenylvinyl)piperidine (in MeCN)
*
MeCN

N  Param.: 9.94

sN Param.: 0.86
***Chem. Eur. J. 2018, 24, 5901-5910
10.1002/chem.201705962
tributylstannane
C12H28Sn*
dichloromethane

N  Param.: 9.96

sN Param.: 0.55
***J. Am. Chem. Soc. 2001, 123, 9500-9512
10.1021/ja010890y
alpha-(N-morpholino)styrene
C12H15NO*
dichloromethane

N  Param.: 9.96

sN Param.: 0.79
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
cyanoborate ion (in water)
*
water

N  Param.: 9.99

sN Param.: 0.54
***Org. Biomol. Chem. 2023, 21, 85-88
10.1039/D2OB02041F
2-(p-anisyl)-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 10.01

sN Param.: 0.72
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
borane-pyridine-complex
*
dichloromethane

N  Param.: 10.01

sN Param.: 0.75
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
2-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.02

sN Param.: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-(2-methyl-4,5-dihydro-1H-imidazol-1-yl)ethanone (in CH2Cl2)
C6H10N2O*
dichloromethane

N  Param.: 10.03

sN Param.: 0.75
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
morpholinoisobutylene
C8H15NO*
dichloromethane

N  Param.: 10.04

sN Param.: 0.82
***Chem. Eur. J. 2003, 9, 2209-2218
10.1002/chem.200204666
[H-B(C6F5)3]- [NEt4]+
*
MeCN

N  Param.: 10.04

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2015, 54, 14508-14512
10.1002/anie.201507298
theophylline anion (in water)
*
water

N  Param.: 10.06

sN Param.: 0.71
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
chloride (in H2O)
Cl*
water

N  Param.: 10.10

sN Param.: 0.60
*J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
2,2,2-trifluoroethylamine (in MeCN)
*
MeCN

N  Param.: 10.13

sN Param.: 0.75
***Eur. J. Org. Chem. 2009, , 6379-6385
10.1002/ejoc.200900925
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate
C18H18BF6LiO2S*
MeCN

N  Param.: 10.13

sN Param.: 0.91
**Angew. Chem. Int. Ed. 2015, 54, 2780-2783
10.1002/anie.201410562
2-(p-tolyl)-1,3-dimethyl-benzimidazoline
*
MeCN

N  Param.: 10.14

sN Param.: 0.70
***Chem. Asian J. 2009, 4, 1824-1829
10.1002/asia.200900322
OH- (in 50/50 water/MeCN)
HO*
water-MeCN mix

N  Param.: 10.19

sN Param.: 0.62
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
N-benzyl-1,4-dihydronicotineamide (in 67W33AN)
*
water-MeCN mix

N  Param.: 10.19

sN Param.: 0.70
*Chem. Eur. J. 2013, 19, 249-263
10.1002/chem.201202839
(E)-1-styryl-2-tritylpyrrolidine (in CH2Cl2)
C31H29N*
dichloromethane

N  Param.: 10.19

sN Param.: 1.06
***J. Am. Chem. Soc. 2014, 136, 14263-14269
10.1021/ja508065e
2,2,2-trifluoroethylamine (in 91M9AN)
C2H4F3N*
MeOH-MeCN mix

N  Param.: 10.20

sN Param.: 0.92
***Angew. Chem. Int. Ed. 2006, 45, 3869-3874
10.1002/anie.200600542
2-methyl-4,5-dihydrothiazole (in CH2Cl2)
C4H7NS*
dichloromethane

N  Param.: 10.20

sN Param.: 0.71
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
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
2,5-dimethyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.21

sN Param.: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
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
chloride (in CF3CH2OH)
Cl*
TFE

N  Param.: 10.30

sN Param.: 0.60
*J. Am. Chem. Soc. 2005, 127, 2641-2649
10.1021/ja045562n
alpha-(N-morpholino)styrene (in MeCN)
C12H15NO*
MeCN

N  Param.: 10.30

sN Param.: 0.80
*Chem. Eur. J. 2018, 24, 5901-5910
10.1002/chem.201705962
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