N-Nucleophiles
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| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
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 |
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 |
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 |
semicarbazide (in water) |
water | N Param.: 11.05 sN Param.: 0.52 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
hydroxylamine (in water) |
water | N Param.: 11.41 sN Param.: 0.55 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2,2,2-trifluoroethylamine (in DMSO) |
DMSO | N Param.: 12.15 sN Param.: 0.65 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in water) |
water | N Param.: 13.33 sN Param.: 0.56 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
ethyl glycinate (in DMSO) |
DMSO | N Param.: 14.30 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
n-propylamine (in DMSO) |
DMSO | N Param.: 15.70 sN Param.: 0.64 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
morpholine (in DMSO) |
DMSO | N Param.: 16.96 sN Param.: 0.67 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
piperidine (in DMSO) |
DMSO | N Param.: 17.19 sN Param.: 0.71 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
thiocyanate (in MeCN) |
MeCN | N Param.: 12.13 sN Param.: 0.60 | | J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u |
2-aminobutan-1-ol (in DMSO) |
DMSO | N Param.: 14.39 sN Param.: 0.67 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
benzylamine (in DMSO) |
DMSO | N Param.: 15.28 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
1-aminopropan-2-ol (in DMSO) |
DMSO | N Param.: 15.47 sN Param.: 0.65 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
diethanolamine (in DMSO) |
DMSO | N Param.: 15.51 sN Param.: 0.70 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
ethanolamine (in DMSO) |
DMSO | N Param.: 16.07 sN Param.: 0.61 | | J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b |
2-pyridone anion (in DMSO) |
DMSO | N Param.: 19.91 sN Param.: 0.60 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in MeCN) |
MeCN | N Param.: 20.11 sN Param.: 0.57 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in water) |
water | N Param.: 12.47 sN Param.: 0.52 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in DMSO) |
DMSO | N Param.: 18.97 sN Param.: 0.62 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in MeCN) |
MeCN | N Param.: 20.22 sN Param.: 0.49 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
4-pyridone anion (in water) |
water | N Param.: 14.76 sN Param.: 0.48 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
acetonitrile (in MeCN) |
MeCN | N Param.: 2.23 sN Param.: 0.84 | | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |
prolinate (in MeCN) |
MeCN | N Param.: 19.95 sN Param.: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-methylpyrrolidine (in MeCN) |
MeCN | N Param.: 16.78 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
pyrrolidine (inMeCN) |
MeCN | N Param.: 18.58 sN Param.: 0.61 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(R)-2-isopropylpyrrolidine |
MeCN | N Param.: 16.44 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2,2-dimethylpyrrolidine |
MeCN | N Param.: 13.96 sN Param.: 0.76 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-benzylpyrrolidine |
MeCN | N Param.: 17.43 sN Param.: 0.66 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-benzhydrylpyrrolidine |
MeCN | N Param.: 16.61 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanamine |
MeCN | N Param.: 17.24 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethyl-1-(pyrrolidin-2-yl)methanamine |
MeCN | N Param.: 17.41 sN Param.: 0.68 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)pyrrolidine |
MeCN | N Param.: 18.33 sN Param.: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(azidomethyl)pyrrolidine |
MeCN | N Param.: 15.43 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-pyrrolidin-2-ylmethanol |
MeCN | N Param.: 16.74 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(methoxymethyl)pyrrolidine |
MeCN | N Param.: 16.50 sN Param.: 0.71 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-(trifluoromethyl)pyrrolidine |
MeCN | N Param.: 11.34 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
methyl L-prolinate |
MeCN | N Param.: 14.75 sN Param.: 0.82 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N,N-dimethylpyrrolidine-2-carboxamide |
MeCN | N Param.: 17.61 sN Param.: 0.67 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-N-propylpyrrolidine-2-carboxamide |
MeCN | N Param.: 15.20 sN Param.: 0.73 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione |
MeCN | N Param.: 15.90 sN Param.: 0.77 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole |
MeCN | N Param.: 15.32 sN Param.: 0.72 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole |
MeCN | N Param.: 15.55 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-3-butyl-1-(pyrrolidin-2-ylmethyl)-1H-imidazol-3-ium trifluoromethanesulfonate |
MeCN | N Param.: 13.57 sN Param.: 0.53 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea |
MeCN | N Param.: 14.97 sN Param.: 0.69 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)urea |
MeCN | N Param.: 17.50 sN Param.: 0.64 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |