Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
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 | |
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 | |
benzimidazole anion (in DMSO) | DMSO | N Param.: 19.13 sN Param.: 0.55 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
benzotriazole anion (in DMSO) | DMSO | N Param.: 16.29 sN Param.: 0.65 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
purine anion (in DMSO) | DMSO | N Param.: 15.03 sN Param.: 0.77 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
theophylline anion (in DMSO) | DMSO | N Param.: 14.78 sN Param.: 0.71 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
adenine anion (in DMSO) | DMSO | N Param.: 18.00 sN Param.: 0.55 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
uracil anion (in DMSO) | DMSO | N Param.: 17.04 sN Param.: 0.63 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
thymine anion (in DMSO) | DMSO | N Param.: 17.63 sN Param.: 0.62 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
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 | |
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 | |
benzotriazole anion (in water) | water | N Param.: 11.52 sN Param.: 0.67 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
purine anion (in water) | water | N Param.: 11.00 sN Param.: 0.54 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
theophylline anion (in water) | water | N Param.: 10.06 sN Param.: 0.71 | 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 | |
guanine anion (in water) | water | N Param.: 11.63 sN Param.: 0.59 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
guanosine anion (in water) | water | N Param.: 12.09 sN Param.: 0.52 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
uracil anion (in water) | water | N Param.: 10.75 sN Param.: 0.53 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
thymine anion (in water) | water | N Param.: 11.17 sN Param.: 0.51 | 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 | |
N-(1-phenylvinyl)acetamide | MeCN | N Param.: 5.73 sN Param.: 0.97 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(1-(4-methoxyphenyl)vinyl)acetamide | MeCN | N Param.: 7.06 sN Param.: 0.85 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(1-(4-chlorophenyl)vinyl)acetamide | MeCN | N Param.: 5.60 sN Param.: 1.00 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
benzyl (1-phenylvinyl)carbamate | MeCN | N Param.: 6.21 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(1-(naphthalen-2-yl)vinyl)acetamide | MeCN | N Param.: 6.28 sN Param.: 0.95 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(3,4-dihydronaphthalen-1-yl)acetamide | MeCN | N Param.: 4.91 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(cyclohex-1-en-1-yl)acetamide | MeCN | N Param.: 5.64 sN Param.: 0.79 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(cyclopent-1-en-1-yl)acetamide | MeCN | N Param.: 7.06 sN Param.: 0.87 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
N-(3,3-dimethylbut-1-en-2-yl)acetamide | MeCN | N Param.: 4.61 sN Param.: 0.98 | Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519 | |
fluoride (in MeOH) | MeOH | N Param.: 11.31 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in 10 % aq MeCN) | water-MeCN mix | N Param.: 8.05 sN Param.: 0.64 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in 60% aq MeCN) | water-MeCN mix | N Param.: 9.75 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in 80% aq MeCN) | water-MeCN mix | N Param.: 11.40 sN Param.: 0.59 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in 90% aq MeCN) | water-MeCN mix | N Param.: 12.27 sN Param.: 0.59 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in 98% aq MeCN) | water-MeCN mix | N Param.: 10.88 sN Param.: 0.83 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
1,1,3,3-tetramethylguanidine | dichloromethane | N Param.: 13.58 sN Param.: 0.77 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2-benzyl-1,1,3,3-tetramethylguanidine | dichloromethane | N Param.: 14.36 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1,3-dimethylimidazolidin-2-imine | dichloromethane | N Param.: 12.46 sN Param.: 0.87 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine | dichloromethane | N Param.: 14.00 sN Param.: 0.70 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO) | dichloromethane | N Param.: 14.44 sN Param.: 0.79 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN) | dichloromethane | N Param.: 16.15 sN Param.: 0.73 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD) | dichloromethane | N Param.: 14.43 sN Param.: 0.81 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine | dichloromethane | N Param.: 16.16 sN Param.: 0.75 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
DBN (in CH2Cl2) | dichloromethane | N Param.: 15.50 sN Param.: 0.76 | ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143 | |
(E)-1-styrylpyrrolidine (in MeCN) | MeCN | N Param.: 13.87 sN Param.: 0.76 | Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962 | |
(S,E)-2-(diphenyl(trimethylsiloxy)methyl)-1-styrylpyrrolidine | MeCN | N Param.: 10.56 sN Param.: 1.01 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
(S,E)-5-benzyl-2,2,3-trimethyl-1-styrylimidazolidin-4-one | MeCN | N Param.: 7.20 sN Param.: 1.14 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
(S,E)-3-benzyl-1-methyl-4-styryl-1,4-diazaspiro[4.4]nonan-2-one | MeCN | N Param.: 7.92 sN Param.: 1.07 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
(2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-1-((E)-styryl)imidazolidin-4-one | MeCN | N Param.: 5.80 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2012, 51, 5739-5742 10.1002/anie.201201240 | |
triphenylphosphine (in THF) | THF | N Param.: 13.59 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
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 | |
DBU (in THF) | THF | N Param.: 16.12 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
MeO-Breslow 1a | THF | N Param.: 14.77 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1b | THF | N Param.: 10.45 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1c | THF | N Param.: 16.61 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
MeO-Breslow 1e | THF | N Param.: 15.65 sN Param.: 0.52 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Dexoxy Breslow intermediate 6 | THF | N Param.: 15.58 sN Param.: 0.57 | Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524 | |
Desoxy Breslow intermediate 2a | THF | N Param.: 17.12 sN Param.: 0.80 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2a | DMSO | N Param.: 17.41 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2a' | THF | N Param.: 14.45 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b | THF | N Param.: 13.91 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2b' | THF | N Param.: 11.42 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
Desoxy Breslow intermediate 2c' | THF | N Param.: 12.75 sN Param.: 0.71 | Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327 | |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 1.47 sN Param.: 0.89 | 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 | |
(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 | |
acetonitrile (in MeCN) | MeCN | N Param.: 2.23 sN Param.: 0.84 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
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 | |
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 | |
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-acetamido-pyridine (in MeCN) | MeCN | N Param.: 13.24 sN Param.: 0.67 | J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247 | |
hydrazine (in water) | water | N Param.: 13.46 sN Param.: 0.57 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylhydrazine (in water) | water | N Param.: 17.23 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylhydrazine (in MeCN) | MeCN | N Param.: 17.73 sN Param.: 0.58 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
1,2-dimethylhydrazine (in MeCN) | MeCN | N Param.: 16.15 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
formohydrazide (in MeCN) | MeCN | N Param.: 10.35 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N',N'-dimethylformohydrazide (in MeCN) | MeCN | N Param.: 15.69 sN Param.: 0.51 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
tert-butyl hydrazinecarboxylate (in MeCN) | MeCN | N Param.: 11.40 sN Param.: 0.70 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
benzohydrazide (in MeCN) | MeCN | N Param.: 12.49 sN Param.: 0.66 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
hydroxylamine (in MeCN) | MeCN | N Param.: 12.80 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N-methylhydroxylamine (in MeCN) | MeCN | N Param.: 14.10 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
ammonia (in MeCN) | MeCN | N Param.: 11.39 sN Param.: 0.69 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methylamine (in MeCN) | MeCN | N Param.: 15.19 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
dimethylamine (in MeCN) | MeCN | N Param.: 17.96 sN Param.: 0.63 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
trimethylamine (in MeCN) | MeCN | N Param.: 23.05 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane | dichloromethane | N Param.: 3.61 sN Param.: 0.79 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
1,3-dioxolane | dichloromethane | N Param.: -2.86 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
2-propyl-1,3-dioxolane | dichloromethane | N Param.: -1.06 sN Param.: 0.81 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetrabutylstannane | dichloromethane | N Param.: -0.30 sN Param.: 1.07 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
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 | |
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 | |
10% water/90% HFIP (w/w) | water-HFIP mix | N Param.: 0.96 sN Param.: 0.93 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
7% water/93% HFIP (w/w) | water-HFIP mix | N Param.: 0.34 sN Param.: 0.96 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
5% water/95% HFIP (w/w) | water-HFIP mix | N Param.: -0.10 sN Param.: 0.97 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
3% water/97% HFIP (w/w) | water-HFIP mix | N Param.: -1.19 sN Param.: 1.08 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
2% water/98% HFIP (w/w) | water-HFIP mix | N Param.: -1.62 sN Param.: 1.10 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
1% water/99% HFIP (w/w) | water-HFIP mix | N Param.: -1.93 sN Param.: 1.09 | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 | |
borane-DMAP-complex | dichloromethane | N Param.: 12.44 sN Param.: 0.76 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |