Mayr's Database of Reactivity Parameters

N-Nucleophiles

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Name Solvent Reactivity
Parameters
Classification Reference
(title or year)
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 14.96

sN Param.: 0.64
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 12.95

sN Param.: 0.58
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 15.30

sN Param.: 0.55
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 16.50

sN Param.: 0.48
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine
*
dichloromethane

N  Param.: 13.45

sN Param.: 0.72
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.67

sN Param.: 0.54
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
1,1,3,3-tetramethylguanidine
C5H13N3*
dichloromethane

N  Param.: 13.58

sN Param.: 0.77
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,1-dimethyl-2-methylenehydrazine (in CH2Cl2)
C3H8N2*
dichloromethane

N  Param.: 19.31

sN Param.: 0.46
***Angew. Chem. Int. Ed. 2013, 52, 11900-11904
10.1002/anie.201305092
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 11.72

sN Param.: 0.73
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,1-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 22.41

sN Param.: 0.45
***Angew. Chem. Int. Ed. 2012, 51, 1353-1356
10.1002/anie.201107315
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)
C6H11N3*
dichloromethane

N  Param.: 16.15

sN Param.: 0.73
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,2-dimethylhydrazine (in MeCN)
*
MeCN

N  Param.: 16.15

sN Param.: 0.68
***J. Org. Chem. 2012, 77, 8142-8155
10.1021/jo301497g
1,3-diaminopropane (in water)
C3H10N2*
water

N  Param.: 14.02

sN Param.: 0.54
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
1,3-dimethylimidazolidin-2-imine
C5H11N3*
dichloromethane

N  Param.: 12.46

sN Param.: 0.87
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1,3-oxazolidin-2-one anion (in DMSO)
*
DMSO

N  Param.: 22.40

sN Param.: 0.59
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
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
1-(trimethylsilyl)-imidazole (in MeCN)
*
MeCN

N  Param.: 11.43

sN Param.: 0.79
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-aminopropan-2-ol (in DMSO)
*
DMSO

N  Param.: 15.47

sN Param.: 0.65
***J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
1-benzyl-2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C16H16N2*
dichloromethane

N  Param.: 13.11

sN Param.: 0.83
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
1-methyl uracil anion (in DMSO)
*
DMSO

N  Param.: 16.36

sN Param.: 0.69
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)
C8H15N3*
dichloromethane

N  Param.: 14.43

sN Param.: 0.81
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
1-methyl-2-phenylpyrrolidine (in CH2Cl2)
C11H15N*
dichloromethane

N  Param.: 16.80

sN Param.: 0.49
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
1-methyl-2-phenylpyrrolidine (in MeCN)
C11H15N*
MeCN

N  Param.: 15.70

sN Param.: 0.54
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
1-methyl-benzimidazole (in MeCN)
*
MeCN

N  Param.: 10.37

sN Param.: 0.82
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-benzotriazole (in MeCN)
*
MeCN

N  Param.: 7.77

sN Param.: 0.76
*Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.90

sN Param.: 0.73
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-methyl-imidazole (in water)
*
water

N  Param.: 9.91

sN Param.: 0.55
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-phenyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.31

sN Param.: 0.67
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
1-phenyl-N-(phenylmethyl)methanimine (in CH2Cl2)
C14H13N*
dichloromethane

N  Param.: 7.90

sN Param.: 0.76
**Z. Naturforsch. B 2013, 68b, 693-699
10.5560/ZNB.2013-3085
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
2,2,2-trifluoroethylamine (in DMSO)
C2H4F3N*
DMSO

N  Param.: 12.15

sN Param.: 0.65
***J. Am. Chem. Soc. 2003, 125, 286-295
10.1021/ja021010y
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
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine
C7H13N3*
dichloromethane

N  Param.: 16.16

sN Param.: 0.75
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine
*
dichloromethane

N  Param.: 14.10

sN Param.: 0.82
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)
C5H9N3*
dichloromethane

N  Param.: 14.44

sN Param.: 0.79
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
*
dichloromethane

N  Param.: 12.98

sN Param.: 0.81
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole
*
dichloromethane

N  Param.: 13.42

sN Param.: 0.73
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
2,4-dimethyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.51

sN Param.: 0.84
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2,4-dimethyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 20.69

sN Param.: 0.60
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
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
2-(naphthylmethyl)quinuclidine (in MeCN)
*
MeCN

N  Param.: 15.66

sN Param.: 0.62
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
2-Ac super-dmap (in MeCN)
*
MeCN

N  Param.: 15.39

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-aminobutan-1-ol (in DMSO)
*
DMSO

N  Param.: 14.39

sN Param.: 0.67
***J. Am. Chem. Soc. 2009, 131, 11392-11401
10.1021/ja903207b
2-benzyl-1,1,3,3-tetramethylguanidine
C12H19N3*
dichloromethane

N  Param.: 14.36

sN Param.: 0.79
***ChemCatChem 2012, 4, 993-999
10.1002/cctc.201200143
2-Bn super-dmap (in MeCN)
*
MeCN

N  Param.: 17.69

sN Param.: 0.57
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Bz super-dmap (in MeCN)
*
MeCN

N  Param.: 14.19

sN Param.: 0.67
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-Et super-dmap (in MeCN)
*
MeCN

N  Param.: 16.81

sN Param.: 0.60
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-formyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 16.06

sN Param.: 0.68
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-formyl-imidazole anion (in water)
*
water

N  Param.: 11.07

sN Param.: 0.50
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-Me super-dmap (in MeCN)
*
MeCN

N  Param.: 16.65

sN Param.: 0.58
***Org. Lett. 2011, 13, 530-533
10.1021/ol1029589
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C5H10N2*
dichloromethane

N  Param.: 15.21

sN Param.: 0.69
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)
C5H10N2*
DMSO

N  Param.: 14.58

sN Param.: 0.79
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)
C5H10N2*
MeCN

N  Param.: 14.43

sN Param.: 0.79
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
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-methyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C4H8N2*
dichloromethane

N  Param.: 12.92

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-methyl-4,5-dihydro-3H-pyrrole (in CH2Cl2)
C5H9N*
dichloromethane

N  Param.: 13.12

sN Param.: 0.69
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
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
2-methyl-benzimidazole (in DMSO)
*
DMSO

N  Param.: 10.02

sN Param.: 0.85
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.74

sN Param.: 0.76
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-imidazole (in water)
*
water

N  Param.: 9.45

sN Param.: 0.54
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
2-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.03

sN Param.: 0.50
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)
C10H12N2*
dichloromethane

N  Param.: 14.62

sN Param.: 0.72
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-phenyl-4,5-dihydro-1H-imidazole (in CH2Cl2)
C9H10N2*
dichloromethane

N  Param.: 12.31

sN Param.: 0.77
***Eur. J. Org. Chem. 2013, , 3369-3377
10.1002/ejoc.201300213
2-phenylethylamine (in water)
C8H11N*
water

N  Param.: 13.40

sN Param.: 0.57
***ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
2-pyridone anion (in DMSO)
*
DMSO

N  Param.: 19.91

sN Param.: 0.60
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
2-pyridone anion (in MeCN)
*
MeCN

N  Param.: 20.11

sN Param.: 0.57
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
2-pyridone anion (in water)
*
water

N  Param.: 12.47

sN Param.: 0.52
***J. Am. Chem. Soc. 2010, 132, 15380-15389
10.1021/ja106962u
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine
*
dichloromethane

N  Param.: 13.00

sN Param.: 0.83
***J. Org. Chem. 2011, 76, 5104-5112
10.1021/jo200803x
3-bromo-4-(dimethylamino)pyridine (in MeCN)
*
MeCN

N  Param.: 12.96

sN Param.: 0.67
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
3-methylpyridine (in CH2Cl2)
C6H7N*
dichloromethane

N  Param.: 10.90

sN Param.: 0.93
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
3-methylpyridine (in MeCN)
C6H7N*
MeCN

N  Param.: 11.50

sN Param.: 0.80
***J. Phys. Org. Chem. 2016, 29, 759-767
10.1002/poc.3580
4,4-dimethyl-glutarimide anion (in DMSO)
*
DMSO

N  Param.: 17.52

sN Param.: 0.63
***J. Org. Chem. 2010, 75, 5250-5258
10.1021/jo1009883
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine
C22H21FN2*
dichloromethane

N  Param.: 14.57

sN Param.: 0.75
***Eur. J. Org. Chem. 2014, , 1202-1211
10.1002/ejoc.201301730
4-(dimethylamino)pyridine (in 91M9AN)
C7H10N2*
MeOH-MeCN mix

N  Param.: 13.20

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in CH2Cl2)
C7H10N2*
dichloromethane

N  Param.: 15.80

sN Param.: 0.66
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMF)
C7H10N2*
DMF

N  Param.: 14.90

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in DMSO)
C7H10N2*
DMSO

N  Param.: 14.80

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in H2O)
C7H10N2*
water

N  Param.: 13.19

sN Param.: 0.56
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-(dimethylamino)pyridine (in MeCN)
C7H10N2*
MeCN

N  Param.: 15.51

sN Param.: 0.62
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
4-(dimethylamino)pyridine (in THF)
*
THF

N  Param.: 15.90

sN Param.: 0.66
***Angew. Chem. Int. Ed. 2011, 50, 6915-6919
10.1002/anie.201102435
4-(morpholino)pyridine (in CH2Cl2)
C9H12N2O*
dichloromethane

N  Param.: 14.59

sN Param.: 0.69
***Eur. J. Org. Chem. 2016, , 4050-4058
10.1002/ejoc.201600572
4-(morpholino)pyridine (in MeCN)
*
MeCN

N  Param.: 14.80

sN Param.: 0.63
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
4-acetamido-pyridine (in MeCN)
*
MeCN

N  Param.: 13.24

sN Param.: 0.67
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
4-amino-3,5-dibromo-pyridine (in MeCN)
*
MeCN

N  Param.: 11.11

sN Param.: 0.75
***J. Phys. Chem. A 2012, 116, 8494-8499
10.1021/jp3049247
4-aminopyridine (in CH2Cl2)
C5H6N2*
dichloromethane

N  Param.: 15.20

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-aminopyridine (in H2O)
C5H6N2*
water

N  Param.: 12.19

sN Param.: 0.66
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-chloroaniline (in MeCN)
C6H6ClN*
MeCN

N  Param.: 12.92

sN Param.: 0.60
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
4-chloropyridine (in CH2Cl2)
C5H4ClN*
dichloromethane

N  Param.: 11.70

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-chloropyridine (in H2O)
C5H4ClN*
water

N  Param.: 10.50

sN Param.: 0.73
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-formyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 16.40

sN Param.: 0.67
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-methoxyaniline (in MeCN)
C7H9NO*
MeCN

N  Param.: 13.42

sN Param.: 0.73
***J. Org. Chem. 2007, 72, 3679-3688
10.1021/jo062586z
4-methoxyaniline (in water)
C7H9NO*
water

N  Param.: 14.28

sN Param.: 0.68
***ChemPlusChem 2015, 80, 1673-1679
10.1002/cplu.201500246
4-methoxypyridine (in CH2Cl2)
C6H7NO*
dichloromethane

N  Param.: 13.70

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methoxypyridine (in H2O)
C6H7NO*
water

N  Param.: 11.44

sN Param.: 0.68
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methyl-imidazole (in MeCN)
*
MeCN

N  Param.: 11.79

sN Param.: 0.77
***Org. Biomol. Chem. 2010, 8, 1929-1935
10.1039/c000965b
4-methyl-imidazole anion (in DMSO)
*
DMSO

N  Param.: 21.29

sN Param.: 0.51
***Chem. Eur. J. 2012, 18, 127-137
10.1002/chem.201102411
4-methyl-quinoline alias lepidine (in MeCN)
*
MeCN

N  Param.: 11.60

sN Param.: 0.62
***J. Org. Chem. 2009, 74, 7157-7164
10.1021/jo901670w
4-methylpyridine (in CH2Cl2)
C6H7N*
dichloromethane

N  Param.: 13.70

sN Param.: 0.67
*Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941
4-methylpyridine (in H2O)
C6H7N*
water

N  Param.: 11.10

sN Param.: 0.75
***Chem. Eur. J. 2007, 13, 336-345
10.1002/chem.200600941