Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-ide (in THF) | THF | N Param.: 23.35 sN Param.: 0.40 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF) | THF | N Param.: 14.07 sN Param.: 0.84 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
thioacetate (in MeCN) | MeCN | N Param.: 21.20 sN Param.: 0.63 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
O-ethyl dithiocarbonate (in MeCN) | MeCN | N Param.: 19.30 sN Param.: 0.69 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
O-isopropyl dithiocarbonate (in MeCN) | MeCN | N Param.: 18.27 sN Param.: 0.78 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
N,N-dimethyl dithiocarbamate (in MeCN) | MeCN | N Param.: 20.93 sN Param.: 0.69 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
pyrrolidin-1-yl dithiocarbamate (in MeCN) | MeCN | N Param.: 22.40 sN Param.: 0.63 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
piperidin-1-yl dithiocarbamate (in MeCN) | MeCN | N Param.: 23.84 sN Param.: 0.57 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
4-methylpiperazin-1-yl dithiocarbamate (in MeCN) | MeCN | N Param.: 23.61 sN Param.: 0.57 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
morpholin-1-yl dithiocarbamate (in MeCN) | MeCN | N Param.: 21.72 sN Param.: 0.64 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
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 | |
toluene | dichloromethane | N Param.: -4.36 sN Param.: 1.77 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
(E)-propenylbenzene | dichloromethane | N Param.: -0.49 sN Param.: 1.18 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2-methylthiophene | dichloromethane | N Param.: 1.35 sN Param.: 0.99 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
allyltrimethylsilane | dichloromethane | N Param.: 1.68 sN Param.: 1.00 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
triethylsilane | dichloromethane | N Param.: 3.58 sN Param.: 0.70 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
methylenecyclohexane | dichloromethane | N Param.: 1.16 sN Param.: 1.04 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2-chloropropene | dichloromethane | N Param.: -3.65 sN Param.: 1.97 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
1-hexene | dichloromethane | N Param.: -2.77 sN Param.: 1.41 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
allylchlorodimethylsilane | dichloromethane | N Param.: -0.57 sN Param.: 1.06 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2,3,3-trimethyl-but-1-ene | dichloromethane | N Param.: 0.06 sN Param.: 1.07 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2,3-dimethyl-but-1-ene | dichloromethane | N Param.: 0.65 sN Param.: 1.00 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2,4,4-trimethyl-pent-1-ene | dichloromethane | N Param.: 0.79 sN Param.: 1.07 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
furan | dichloromethane | N Param.: 1.33 sN Param.: 1.29 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
norbornene | dichloromethane | N Param.: -0.25 sN Param.: 1.09 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
1-methylcyclopentene | dichloromethane | N Param.: 1.18 sN Param.: 1.17 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
trifluoroethanol | TFE | N Param.: 1.11 sN Param.: 0.96 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
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 | |
2-methyl-pent-1-ene | dichloromethane | N Param.: 0.84 sN Param.: 1.06 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
hydrazine (in MeCN) | MeCN | N Param.: 16.45 sN Param.: 0.56 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
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 | |
trimethylhydrazine (in MeCN) | MeCN | N Param.: 12.43 sN Param.: 0.75 | 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 | |
trimethylhydrazine (in MeCN) | MeCN | N Param.: 17.75 sN Param.: 0.53 | Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315 | |
(5-methyl-furan-2-yl) pinacol boronate | MeCN | N Param.: 2.90 sN Param.: 0.98 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
(5-methyl-furan-2-yl) MDA boronate | MeCN | N Param.: 6.38 sN Param.: 0.86 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
(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 | |
(5-methyl-furan-2-yl) trifluoroborate | MeCN | N Param.: 7.66 sN Param.: 1.04 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
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 | |
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate | MeCN | N Param.: 12.55 sN Param.: 0.92 | Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a | |
dipp Imd boronate | dichloromethane | N Param.: 9.55 sN Param.: 0.81 | Org. Lett. 2012, 14, 82-85 10.1021/ol202836p | |
Me2 Imd boronate | dichloromethane | N Param.: 11.88 sN Param.: 0.71 | Org. Lett. 2012, 14, 82-85 10.1021/ol202836p | |
imidazole anion (in DMSO) | DMSO | N Param.: 21.09 sN Param.: 0.51 | Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411 | |
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 | |
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 | |
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 | |
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 | |
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-(p-tolyl)vinyl)acetamide | MeCN | N Param.: 6.57 sN Param.: 0.91 | 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-phenylvinyl)benzamide | MeCN | N Param.: 5.44 sN Param.: 1.00 | 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 80% aq EtOH) | water-EtOH mix | N Param.: 13.20 sN Param.: 0.53 | J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z | |
fluoride (in water) | water | N Param.: 7.70 sN Param.: 0.66 | 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 | |
(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 |