Nucleophiles
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 | |
benzyldimethylsilane![]() ![]() |
dichloromethane | N Param.: 2.78 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
beta-(trimethylsilyl)styrene![]() ![]() |
dichloromethane | N Param.: -0.43 sN Param.: 1.06 | Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215 | |
beta-alanine (anionic, in water)![]() ![]() |
water | N Param.: 13.26 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
beta-piperidinium-peroxypropionate![]() ![]() |
water | N Param.: 13.94 sN Param.: 0.62 | Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158 | |
bis(4-(dimethylamino)phenyl)phenylmethane (in MeCN)![]() ![]() |
MeCN | N Param.: -4.20 sN Param.: 0.82 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
bis(4-methoxyphenyl)methane (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: -2.11 sN Param.: 0.98 | J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y | |
bis(4-methoxyphenyl)phenylmethane (in MeCN)![]() ![]() |
MeCN | N Param.: -7.00 sN Param.: 0.82 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
bis(4-nitrophenyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 19.92 sN Param.: 0.67 | ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...] | |
bis(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 15.68 sN Param.: 0.74 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
borane-2,6-lutidine-complex![]() ![]() |
dichloromethane | N Param.: 10.33 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-4-methoxypyridine-complex![]() ![]() |
dichloromethane | N Param.: 11.01 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-4-tBu-pyridine-complex![]() ![]() |
dichloromethane | N Param.: 10.46 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-DMAP-complex![]() ![]() |
dichloromethane | N Param.: 12.44 sN Param.: 0.76 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-N,N-diethylaniline-complex![]() ![]() |
dichloromethane | N Param.: 8.53 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-N,N-diisopropylaniline-complex![]() ![]() |
dichloromethane | N Param.: 8.84 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-N-ethyl-N-isopropylaniline-complex![]() ![]() |
dichloromethane | N Param.: 9.12 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-pyridine-complex![]() ![]() |
dichloromethane | N Param.: 10.01 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
borane-triethylamine-complex![]() ![]() |
dichloromethane | N Param.: 8.90 sN Param.: 0.75 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
borane-trimethylamine-complex![]() ![]() |
dichloromethane | N Param.: 7.97 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
bromide (in 20% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 40% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 50% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 13.60 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 50% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 13.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in 80% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 14.50 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in CF3CH2OH)![]() ![]() |
TFE | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromide (in H2O)![]() ![]() |
water | N Param.: 11.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
bromite (in water)![]() ![]() |
water | N Param.: 12.75 sN Param.: 0.59 | Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...] | |
bromo(phenylsulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 23.90 sN Param.: 0.62 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
bromoborane-triethylamine-complex![]() ![]() |
dichloromethane | N Param.: 7.49 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
BTM (in CH2Cl2)![]() ![]() |
dichloromethane | N Param.: 13.06 sN Param.: 0.73 | Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865 | |
Bu4NBH4 (in DMSO)![]() ![]() |
DMSO | N Param.: 14.94 sN Param.: 0.79 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
buta-1,3-diene![]() ![]() |
dichloromethane | N Param.: -0.87 sN Param.: 1.00 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
butyltrimethylsilane![]() ![]() |
dichloromethane | N Param.: -5.40 sN Param.: 1.10 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
chloride (in 20% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 11.31 sN Param.: 0.58 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 40% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 11.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 11.80 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 50/50 MeOH/MeCN)![]() ![]() |
MeOH-MeCN mix | N Param.: 14.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 60% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 12.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq EtOH)![]() ![]() |
water-EtOH mix | N Param.: 13.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in 80% aq MeCN)![]() ![]() |
water-MeCN mix | N Param.: 13.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in CF3CH2OH)![]() ![]() |
TFE | N Param.: 10.30 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in EtOH)![]() ![]() |
EtOH | N Param.: 14.70 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in H2O)![]() ![]() |
water | N Param.: 10.10 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in hexafluoroisopropanol)![]() ![]() |
HFIP | N Param.: 8.00 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in MeCN)![]() ![]() |
MeCN | N Param.: 17.20 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloride (in MeOH)![]() ![]() |
MeOH | N Param.: 12.90 sN Param.: 0.60 | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n | |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)![]() ![]() |
DMSO | N Param.: 26.90 sN Param.: 0.45 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 |



















































