Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
[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 | |
[H-B(2,6-F2C6H3)3]- [NEt4]+ | MeCN | N Param.: 13.97 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298 | |
[H-B(2,4,6-F3C6H2)3]- [NEt4]+ | MeCN | N Param.: 14.13 sN Param.: 0.61 | Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298 | |
Z-3-(trimethylsiloxy)pent-2-ene | dichloromethane | N Param.: 5.58 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
xanthene | dichloromethane | N Param.: 0.64 sN Param.: 0.97 | J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538 | |
water (in MeCN) | MeCN | N Param.: 5.79 sN Param.: 0.72 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
valine (anionic, in water) | water | N Param.: 13.65 sN Param.: 0.57 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
uracil anion (in water) | water | N Param.: 10.75 sN Param.: 0.53 | 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 | |
tris(4-methylphenyl)phosphane | dichloromethane | N Param.: 15.44 sN Param.: 0.64 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tris(4-methoxyphenyl)phosphane | dichloromethane | N Param.: 16.17 sN Param.: 0.62 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tris(4-methoxyphenyl)methane (in MeCN) | MeCN | N Param.: -5.18 sN Param.: 0.82 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris(4-dimethylaminophenyl)phosphane | dichloromethane | N Param.: 18.39 sN Param.: 0.64 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tris(4-chlorophenyl)phosphane | dichloromethane | N Param.: 12.58 sN Param.: 0.65 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tris(4-(dimethylamino)phenyl)methane (in MeCN) | MeCN | N Param.: -3.30 sN Param.: 0.82 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris(2-methylphenyl)phosphane | dichloromethane | N Param.: 8.56 sN Param.: 0.70 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2-methoxyphenyl)phosphane | dichloromethane | N Param.: 14.26 sN Param.: 0.73 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2,6-dimethoxyphenyl)phosphane (in MeCN) | MeCN | N Param.: 18.11 sN Param.: 0.62 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2,6-dimethoxyphenyl)phosphane | dichloromethane | N Param.: 15.19 sN Param.: 0.88 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris(2,4-dimethylphenyl)phosphane | dichloromethane | N Param.: 14.88 sN Param.: 0.41 | Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080 | |
tris((trimethylsilyl)methyl)silane | dichloromethane | N Param.: 3.59 sN Param.: 0.67 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris((dimethyl(phenyl)silyl)methyl)silane | dichloromethane | N Param.: 3.40 sN Param.: 0.66 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tris((butyldimethylsilyl)methyl)silane | dichloromethane | N Param.: 3.73 sN Param.: 0.68 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tripropylsilane | dichloromethane | N Param.: 3.67 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triphenylstannane | dichloromethane | N Param.: 5.64 sN Param.: 0.59 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
triphenylsilane | dichloromethane | N Param.: 2.65 sN Param.: 0.72 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triphenylphosphine (in THF) | THF | N Param.: 13.59 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435 | |
triphenylphosphane | dichloromethane | N Param.: 14.33 sN Param.: 0.65 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
triphenylmethane | dichloromethane | N Param.: -4.27 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triphenylgermane | dichloromethane | N Param.: 3.99 sN Param.: 0.62 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
triphenyl phosphite | dichloromethane | N Param.: 5.51 sN Param.: 0.76 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
trimethylsilane | dichloromethane | N Param.: 3.15 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethylhydrazine (in MeCN) | MeCN | N Param.: 17.75 sN Param.: 0.53 | 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 | |
trimethylamine (in MeCN) | MeCN | N Param.: 23.05 sN Param.: 0.45 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
trimethyl(prenyl)silane | dichloromethane | N Param.: 0.90 sN Param.: 1.17 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
trimethyl(phenethyl)stannane | 1,2-dichloroethane | N Param.: -1.10 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(phenethyl)silane | dichloromethane | N Param.: -3.50 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(4-methylphenethyl)stannane | 1,2-dichloroethane | N Param.: -0.50 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(3-(trimethylstannyl)propyl)silane (in MeCN) | MeCN | N Param.: -3.40 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(3-(trimethylstannyl)propyl)germane (in MeCN) | MeCN | N Param.: -2.40 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(3-(trimethylplumbyl)propyl)silane (in MeCN) | MeCN | N Param.: -1.20 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(3-(trimethylplumbyl)propyl)germane (in MeCN) | MeCN | N Param.: -1.00 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl(3-(trimethylgermyl)propyl)silane (in MeCN) | MeCN | N Param.: -4.80 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trimethyl phosphite (in 91M9AN) | MeOH-MeCN mix | N Param.: 9.04 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
triisopropylsilane | dichloromethane | N Param.: 2.93 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triisopropylphosphane | dichloromethane | N Param.: 13.37 sN Param.: 0.70 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
trihexylsilane | dichloromethane | N Param.: 3.89 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trifluoroethanol | TFE | N Param.: 1.11 sN Param.: 0.96 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
trifluoroacetamide anion (in DMSO) | DMSO | N Param.: 15.81 sN Param.: 0.64 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
triethylsilane | dichloromethane | N Param.: 3.58 sN Param.: 0.70 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
triethylgermane | dichloromethane | N Param.: 4.00 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
triethylamine (in MeCN) | MeCN | N Param.: 17.10 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
triethylamine (in CH2Cl2) | dichloromethane | N Param.: 17.30 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
triethoxysilane | dichloromethane | N Param.: -1.80 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tricyclohexylphosphane | dichloromethane | N Param.: 14.64 sN Param.: 0.68 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tributylstannane | dichloromethane | N Param.: 9.96 sN Param.: 0.55 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tributylsilane | dichloromethane | N Param.: 3.99 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tributylgermane | dichloromethane | N Param.: 5.92 sN Param.: 0.73 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
tributyl phosphite | dichloromethane | N Param.: 10.36 sN Param.: 0.70 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
tri-p-tolylmethane (in MeCN) | MeCN | N Param.: -8.80 sN Param.: 0.82 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tri-p-tolylmethane | dichloromethane | N Param.: -3.62 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tri-n-butylphosphane | dichloromethane | N Param.: 15.49 sN Param.: 0.69 | Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696 | |
trans-HMo(CO)2(PPh3)Cp | dichloromethane | N Param.: 6.60 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trans-HMo(CO)2(PMe3)Cp | dichloromethane | N Param.: 7.80 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
trans-HMo(CO)2(PCy3)Cp | dichloromethane | N Param.: 6.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
toluene | dichloromethane | N Param.: -4.36 sN Param.: 1.77 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
thymine anion (in water) | water | N Param.: 11.17 sN Param.: 0.51 | 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 | |
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine) | dichloromethane | N Param.: 14.45 sN Param.: 0.78 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
threonine (anionic, in water) | water | N Param.: 12.69 sN Param.: 0.60 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
thiophenolate (in DMSO) | DMSO | N Param.: 23.36 sN Param.: 0.74 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
thiophene | dichloromethane | N Param.: -1.01 sN Param.: 1.10 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
thiocyanate (in MeCN) | MeCN | N Param.: 12.13 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
thiocyanate (in MeCN) | MeCN | N Param.: 17.94 sN Param.: 0.60 | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u | |
thioacetate (in MeCN) | MeCN | N Param.: 21.20 sN Param.: 0.63 | Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j | |
theophylline anion (in water) | water | N Param.: 10.06 sN Param.: 0.71 | 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 | |
tetrapropylstannane (in 1,2-DCE) | 1,2-dichloroethane | N Param.: -0.50 sN Param.: 1.13 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetramethylethylene | dichloromethane | N Param.: -1.00 sN Param.: 1.40 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
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 | |
tetraisobutylstannane | dichloromethane | N Param.: 1.35 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetrahydrothiopyran (in CH2Cl2) | dichloromethane | N Param.: 11.94 sN Param.: 0.75 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
tetrahydrothiophene (in MeCN) | MeCN | N Param.: 13.30 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
tetrahydrothiophene (in CH2Cl2) | dichloromethane | N Param.: 13.10 sN Param.: 0.72 | Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977 | |
tetrahydrofuran (in dichloromethane) | dichloromethane | N Param.: -3.50 sN Param.: 0.80 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetrahydroborate ion (in water) | water | N Param.: 12.10 sN Param.: 0.79 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetraethylstannane (in MeCN) | MeCN | N Param.: -2.40 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetraethylstannane (in 1,2-DCE) | 1,2-dichloroethane | N Param.: -1.90 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetraethylsilane | MeCN | N Param.: -6.50 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetraethylplumbane (in MeCN) | MeCN | N Param.: 0.10 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tetraethylgermane (in MeCN) | MeCN | N Param.: -4.70 sN Param.: 1.10 | 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 | |
tetra-sec.butylstannane (in 1,2-DCE) | 1,2-dichloroethane | N Param.: -1.10 sN Param.: 1.15 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
tert-butylamine (in water) | water | N Param.: 10.48 sN Param.: 0.65 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
tert-butylamine (in MeCN) | MeCN | N Param.: 12.35 sN Param.: 0.72 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
tert-butyl isocyanide | dichloromethane | N Param.: 5.47 sN Param.: 0.77 | Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205 | |
tert-butyl indole-1-carboxylate | MeCN | N Param.: 1.68 sN Param.: 1.26 | J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655 | |
tert-butyl hydrazinecarboxylate (in MeCN) | MeCN | N Param.: 11.40 sN Param.: 0.70 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
tert-butanol (in MeCN) | MeCN | N Param.: 5.35 sN Param.: 0.72 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 |