Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
7-azaindole | MeCN | N Param.: 3.87 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
ammonia (in water) | water | N Param.: 9.48 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methylamine (in water) | water | N Param.: 13.85 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethylamine (in water) | water | N Param.: 12.87 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
isopropylamine (in water) | water | N Param.: 12.00 sN Param.: 0.56 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
tert-butylamine (in water) | water | N Param.: 10.48 sN Param.: 0.65 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
dimethylamine (in water) | water | N Param.: 17.12 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
diethylamine (in water) | water | N Param.: 14.68 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
pyrrolidine (in water) | water | N Param.: 17.21 sN Param.: 0.49 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperidine (in water) | water | N Param.: 18.13 sN Param.: 0.44 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
morpholine (in water) | water | N Param.: 15.62 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
piperazine (in water) | water | N Param.: 17.22 sN Param.: 0.50 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
perhydroazepine (in water) | water | N Param.: 18.29 sN Param.: 0.46 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycinenitrile (in water) | water | N Param.: 10.80 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethanolamine (in water) | water | N Param.: 12.61 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
ethylenediamine (in water) | water | N Param.: 13.28 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
propargylamine (in water) | water | N Param.: 12.29 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
allylamine (in water) | water | N Param.: 13.21 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
benzylamine (in water) | water | N Param.: 13.44 sN Param.: 0.55 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
4-chloroaniline (in MeCN) | MeCN | N Param.: 12.92 sN Param.: 0.60 | 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 | |
aniline (in MeCN) | MeCN | N Param.: 12.64 sN Param.: 0.68 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
p-toluidine (in water) | water | N Param.: 13.00 sN Param.: 0.79 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
p-toluidine (in MeCN) | MeCN | N Param.: 13.19 sN Param.: 0.69 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
4-methoxyaniline (in MeCN) | MeCN | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
diethanolamine (in water) | water | N Param.: 13.00 sN Param.: 0.61 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
N-methyl-glycinenitrile (in water) | water | N Param.: 13.50 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methyl glycinate (in water) | water | N Param.: 12.08 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
glycineamide (in water) | water | N Param.: 12.29 sN Param.: 0.58 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
1,3-diaminopropane (in water) | water | N Param.: 14.02 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO) | DMSO | N Param.: 27.28 sN Param.: 0.50 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 4-cyanobenzyl-CN (in DMSO) | DMSO | N Param.: 25.11 sN Param.: 0.54 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 4-nitrobenzyl-CN (in DMSO) | DMSO | N Param.: 19.67 sN Param.: 0.68 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-phenyl-propionitrile (in DMSO) | DMSO | N Param.: 28.95 sN Param.: 0.58 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO) | DMSO | N Param.: 25.35 sN Param.: 0.56 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) | DMSO | N Param.: 19.61 sN Param.: 0.60 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
6-methoxy-quinoline (in MeCN) | MeCN | N Param.: 10.86 sN Param.: 0.66 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
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 | |
2-(naphthylmethyl)quinuclidine (in MeCN) | MeCN | N Param.: 15.66 sN Param.: 0.62 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
quinine | dichloromethane | N Param.: 10.46 sN Param.: 0.75 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
quinidine | dichloromethane | N Param.: 10.54 sN Param.: 0.74 | J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w | |
phthalimide anion (in DMSO) | DMSO | N Param.: 15.52 sN Param.: 0.67 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
succinimide anion (in DMSO) | DMSO | N Param.: 16.03 sN Param.: 0.66 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
maleimide anion (in DMSO) | DMSO | N Param.: 14.87 sN Param.: 0.76 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
trifluoroacetamide anion (in DMSO) | DMSO | N Param.: 15.81 sN Param.: 0.64 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
N-methyl-trifluoroacetamide anion (in DMSO) | DMSO | N Param.: 15.70 sN Param.: 0.71 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
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 | |
diacetamide anion (in DMSO) | DMSO | N Param.: 16.05 sN Param.: 0.70 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
cyanamide anion (in DMSO) | DMSO | N Param.: 20.33 sN Param.: 0.64 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
p-toluenesulfonamide anion (in DMSO) | DMSO | N Param.: 17.14 sN Param.: 0.60 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
methanesulfonamide anion (in DMSO) | DMSO | N Param.: 18.61 sN Param.: 0.53 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
hydantoin anion (in DMSO) | DMSO | N Param.: 17.52 sN Param.: 0.55 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
1,3-oxazolidin-2-one anion (in DMSO) | DMSO | N Param.: 22.40 sN Param.: 0.59 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
(S)-4-benzyl-1,3-oxazolidin-2-one anion (in DMSO) | DMSO | N Param.: 22.67 sN Param.: 0.54 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
ethyl N-acetylcarbamate anion (in DMSO) | DMSO | N Param.: 15.99 sN Param.: 0.70 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
saccharin anion (in MeCN) | MeCN | N Param.: 10.78 sN Param.: 0.89 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
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 | |
2,3,5,6-tetrahydroimidazo[2,1-b]thiazole | dichloromethane | N Param.: 12.98 sN Param.: 0.81 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole | dichloromethane | N Param.: 13.42 sN Param.: 0.73 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine | dichloromethane | N Param.: 14.10 sN Param.: 0.82 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
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 | |
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 | |
(S)-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 13.45 sN Param.: 0.72 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(2S,3S)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 14.96 sN Param.: 0.64 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 15.30 sN Param.: 0.55 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 16.50 sN Param.: 0.48 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
(R)-2-(tert-butyl)-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine | dichloromethane | N Param.: 12.95 sN Param.: 0.58 | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x | |
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 | |
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 | |
chloro(phenylsulfonyl)methanide (in DMSO) | DMSO | N Param.: 28.27 sN Param.: 0.42 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
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 | |
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Param.: 25.59 sN Param.: 0.51 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Param.: 24.88 sN Param.: 0.49 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
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 | |
barbiturate anion (in DMSO) | DMSO | N Param.: 15.59 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-dimethylbarbiturate anion (in DMSO) | DMSO | N Param.: 17.46 sN Param.: 0.72 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
2-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.24 sN Param.: 0.82 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-diethyl-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.90 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
p-nitrophenolate (in DMSO) | DMSO | N Param.: 14.32 sN Param.: 0.77 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
p-nitrophenolate (in MeCN) | MeCN | N Param.: 15.14 sN Param.: 0.82 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 |