N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
2-tritylpyrrolidine |
MeCN | N Param.: 9.16 sN Param.: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
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) |
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) |
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 |
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) |
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) |
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) |
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) |
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) |
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) |
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) |
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) |
dichloromethane | N Param.: 15.20 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-aminopyridine (in H2O) |
water | N Param.: 12.19 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-chloroaniline (in MeCN) |
MeCN | N Param.: 12.92 sN Param.: 0.60 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-chloropyridine (in CH2Cl2) |
dichloromethane | N Param.: 11.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-chloropyridine (in H2O) |
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) |
MeCN | N Param.: 13.42 sN Param.: 0.73 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
4-methoxyaniline (in water) |
water | N Param.: 14.28 sN Param.: 0.68 | | ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246 |
4-methoxypyridine (in CH2Cl2) |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-methoxypyridine (in H2O) |
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) |
dichloromethane | N Param.: 13.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-methylpyridine (in H2O) |
water | N Param.: 11.10 sN Param.: 0.75 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-nitro-imidazole anion (in DMSO) |
DMSO | N Param.: 14.81 sN Param.: 0.71 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-nitro-imidazole anion (in water) |
water | N Param.: 11.37 sN Param.: 0.53 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
4-pyridone anion (in DMSO) |
DMSO | N Param.: 18.97 sN Param.: 0.62 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in MeCN) |
MeCN | N Param.: 20.22 sN Param.: 0.49 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in water) |
water | N Param.: 14.76 sN Param.: 0.48 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyrrolidinopyridine (in CH2Cl2) |
dichloromethane | N Param.: 15.90 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in H2O) |
water | N Param.: 12.39 sN Param.: 0.66 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
4-pyrrolidinopyridine (in MeCN) |
MeCN | N Param.: 14.99 sN Param.: 0.69 | | Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452 |
5,6-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 11.08 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methoxy-benzimidazole (in DMSO) |
DMSO | N Param.: 11.00 sN Param.: 0.71 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-methyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.69 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
6-methoxy-quinoline (in MeCN) |
MeCN | N Param.: 10.86 sN Param.: 0.66 | | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w |
9-methyl guanine anion (in water) |
water | N Param.: 10.77 sN Param.: 0.65 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
acetonitrile (in MeCN) |
MeCN | N Param.: 2.23 sN Param.: 0.84 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
adenine anion (in DMSO) |
DMSO | N Param.: 18.00 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
adenine anion (in water) |
water | N Param.: 10.93 sN Param.: 0.62 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
alanine (anionic, in water) |
water | N Param.: 13.01 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
allylamine (in MeCN) |
MeCN | N Param.: 14.37 sN Param.: 0.66 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
allylamine (in water) |
water | N Param.: 13.21 sN Param.: 0.54 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
ammonia (in MeCN) |
MeCN | N Param.: 11.39 sN Param.: 0.69 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
ammonia (in water) |
water | N Param.: 9.48 sN Param.: 0.59 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in MeCN) |
MeCN | N Param.: 12.64 sN Param.: 0.68 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
aniline (in water) |
water | N Param.: 12.99 sN Param.: 0.73 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
arginine (betaine, in water) |
water | N Param.: 12.96 sN Param.: 0.57 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
asparagine (anionic, in water) |
water | N Param.: 13.03 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
aspartate (dianionic, in water) |
water | N Param.: 13.81 sN Param.: 0.53 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
azide ion (in 45M55AN) |
MeOH-MeCN mix | N Param.: 15.01 sN Param.: 0.80 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91E9AN) |
EtOH-MeCN mix | N Param.: 16.30 sN Param.: 0.73 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91iPr9AN) |
iPrOH-MeCN mix | N Param.: 17.07 sN Param.: 0.71 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91M9AN) |
MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in 91nPr9AN) |
nPrOH-MeCN mix | N Param.: 16.70 sN Param.: 0.73 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
azide ion (in DMSO) |
DMSO | N Param.: 20.50 sN Param.: 0.59 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
benzimidazole (in DMSO) |
DMSO | N Param.: 10.50 sN Param.: 0.79 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzimidazole anion (in DMSO) |
DMSO | N Param.: 19.13 sN Param.: 0.55 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzohydrazide (in MeCN) |
MeCN | N Param.: 12.49 sN Param.: 0.66 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
benzotriazole (in MeCN) |
MeCN | N Param.: 7.69 sN Param.: 0.76 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
benzotriazole anion (in DMSO) |
DMSO | N Param.: 16.29 sN Param.: 0.65 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzotriazole anion (in water) |
water | N Param.: 11.52 sN Param.: 0.67 | | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 |
benzylamine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 13.46 sN Param.: 0.62 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
benzylamine (in DMSO) |
DMSO | N Param.: 15.28 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
benzylamine (in MeCN) |
MeCN | N Param.: 14.29 sN Param.: 0.67 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
benzylamine (in water) |
water | N Param.: 13.44 sN Param.: 0.55 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
beta-alanine (anionic, in water) |
water | N Param.: 13.26 sN Param.: 0.58 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
cyanamide anion (in DMSO) |
DMSO | N Param.: 20.33 sN Param.: 0.64 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
cyanate (in MeCN) |
MeCN | N Param.: 13.60 sN Param.: 0.84 | | Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314 |
cysteine (dianionic, in water, S-nucleophile!) |
water | N Param.: 23.43 sN Param.: 0.42 | | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h |
DABCO (in MeCN) |
MeCN | N Param.: 18.80 sN Param.: 0.70 | | Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489 |
DBN (in CH2Cl2) |
dichloromethane | N Param.: 15.50 sN Param.: 0.76 | | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 |
DBN (in MeCN) |
MeCN | N Param.: 16.28 sN Param.: 0.67 | | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
DBU (in MeCN) |
MeCN | N Param.: 15.29 sN Param.: 0.70 | | Chem. Commun. 2008, , 1792-1794 10.1039/b801811a |
DBU (in THF) |
THF | N Param.: 16.12 sN Param.: 0.67 | | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 |
DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine) |
dichloromethane | N Param.: 13.86 sN Param.: 0.78 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
di(methoxyethyl)amine (in MeCN) |
MeCN | N Param.: 13.24 sN Param.: 0.93 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
diacetamide anion (in DMSO) |
DMSO | N Param.: 16.05 sN Param.: 0.70 | | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 |
diethanolamine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 13.71 sN Param.: 0.67 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
diethanolamine (in DMSO) |
DMSO | N Param.: 15.51 sN Param.: 0.70 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
diethanolamine (in water) |
water | N Param.: 13.00 sN Param.: 0.61 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
diethylamine (in MeCN) |
MeCN | N Param.: 15.10 sN Param.: 0.73 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
diethylamine (in water) |
water | N Param.: 14.68 sN Param.: 0.53 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
dimethylamine (in MeCN) |
MeCN | N Param.: 17.96 sN Param.: 0.63 | | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g |
dimethylamine (in water) |
water | N Param.: 17.12 sN Param.: 0.50 | | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z |
dipropylamine (in MeCN) |
MeCN | N Param.: 14.51 sN Param.: 0.80 | | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 |
ethanolamine (in 91M9AN) |
MeOH-MeCN mix | N Param.: 13.23 sN Param.: 0.65 | | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 |
ethanolamine (in DMSO) |
DMSO | N Param.: 16.07 sN Param.: 0.61 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |