Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
o-(trifluoromethyl)phenolate (in DMF) | DMF | N Param.: 20.37 sN Param.: 0.58 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
o,o'-di-tert-butylphenolate (in DMSO) | DMSO | N Param.: 21.02 sN Param.: 0.59 | J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485 | |
norbornene | dichloromethane | N Param.: -0.25 sN Param.: 1.09 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
nitrite ion (in MeCN) | MeCN | N Param.: 17.20 sN Param.: 0.72 | Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274 | |
nicotine (in MeCN) | MeCN | N Param.: 11.60 sN Param.: 0.81 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
nicotine (in CH2Cl2) | dichloromethane | N Param.: 10.40 sN Param.: 1.04 | J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580 | |
naphthalene-2-thiolate (in DMSO) | DMSO | N Param.: 22.55 sN Param.: 0.83 | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 | |
NADPH (in water) | water | N Param.: 10.68 sN Param.: 0.54 | Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F | |
NADH (in water) | water | N Param.: 10.37 sN Param.: 0.54 | Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F | |
NaBH4 (in DMSO) | DMSO | N Param.: 14.74 sN Param.: 0.81 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
NaBH3(CN) (in DMSO) | DMSO | N Param.: 11.52 sN Param.: 0.67 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
NaB(OAc)3H (in DMSO) | DMSO | N Param.: 14.45 sN Param.: 0.76 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
N-vinylcarbazole | dichloromethane | N Param.: 5.02 sN Param.: 0.94 | Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l | |
n-propylamine (in water) | water | N Param.: 13.33 sN Param.: 0.56 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
n-propylamine (in MeCN) | MeCN | N Param.: 15.11 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
n-propylamine (in DMSO) | DMSO | N Param.: 15.70 sN Param.: 0.64 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
n-propylamine (in 91M9AN) | MeOH-MeCN mix | N Param.: 13.41 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
n-propanolate (in propan-1-ol) | nPrOH | N Param.: 16.03 sN Param.: 0.70 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
n-propanolate (in 91nPr9AN) | nPrOH-MeCN mix | N Param.: 16.73 sN Param.: 0.63 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
N-phenylpropan-2-imine (in CH2Cl2) | dichloromethane | N Param.: 9.53 sN Param.: 0.85 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-phenylcyclohexanimine (in CH2Cl2) | dichloromethane | N Param.: 8.80 sN Param.: 1.00 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-phenyl-1,4-dihydronicotineamide | dichloromethane | N Param.: 7.53 sN Param.: 0.87 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
N-methylpyrrole | dichloromethane | N Param.: 5.85 sN Param.: 1.03 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
N-methylindole | dichloromethane | N Param.: 5.75 sN Param.: 1.23 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
N-methylhydroxylamine (in MeCN) | MeCN | N Param.: 14.10 sN Param.: 0.76 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
N-methylenepyrrolidin-1-amine (in CH2Cl2) | dichloromethane | N Param.: 7.84 sN Param.: 0.89 | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 | |
N-methylenepyrrolidin-1-amine (in CH2Cl2) | dichloromethane | N Param.: 17.90 sN Param.: 0.48 | Angew. Chem. Int. Ed. 2013, 52, 11900-11904 10.1002/anie.201305092 | |
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 | |
N-methyl-pyrrolidine (in MeCN) | MeCN | N Param.: 20.59 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-pyrrolidine (in CH2Cl2) | dichloromethane | N Param.: 20.60 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-piperidine (in MeCN) | MeCN | N Param.: 18.72 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-piperidine (in CH2Cl2) | dichloromethane | N Param.: 18.90 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-morpholine (in MeCN) | MeCN | N Param.: 16.80 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-morpholine (in CH2Cl2) | dichloromethane | N Param.: 16.50 sN Param.: 0.52 | J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707 | |
N-methyl-glycinenitrile (in water) | water | N Param.: 13.50 sN Param.: 0.59 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
N-methyl-1-phenylmethanimine (in CH2Cl2) | dichloromethane | N Param.: 8.60 sN Param.: 0.77 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
n-butylamine (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.63 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
n-butyl vinyl ether | dichloromethane | N Param.: 3.76 sN Param.: 0.91 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
N-benzyl-N-(but-1-yn-1-yl)-4-methylbenzenesulfonamide | dichloromethane | N Param.: 5.16 sN Param.: 0.85 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
N-benzyl-N-((2-methoxyphenyl)ethynyl)-4-methylbenzenesulfonamide | dichloromethane | N Param.: 4.40 sN Param.: 0.86 | Angew. Chem. Int. Ed. 2014, 53, 4968-4971 10.1002/anie.201402055 | |
N-benzyl-1,4-dihydronicotineamide (in MeCN) | MeCN | N Param.: 9.80 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-benzyl-1,4-dihydronicotineamide (in 90W10AN) | water-MeCN mix | N Param.: 11.35 sN Param.: 0.66 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
N-benzyl-1,4-dihydronicotineamide (in 80W20AN) | water-MeCN mix | N Param.: 10.67 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-benzyl-1,4-dihydronicotineamide (in 67W33AN) | water-MeCN mix | N Param.: 10.19 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-benzyl-1,4-dihydronicotineamide (in 50W50AN) | water-MeCN mix | N Param.: 9.79 sN Param.: 0.70 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
N-benzyl-1,4-dihydronicotineamide | dichloromethane | N Param.: 8.67 sN Param.: 0.82 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
N-(triisopropylsilyl)pyrrole | dichloromethane | N Param.: 3.12 sN Param.: 0.93 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
N-(phenylmethyl)propan-2-imine (in CH2Cl2) | dichloromethane | N Param.: 11.13 sN Param.: 0.73 | Z. Naturforsch. B 2013, 68b, 693-699 10.5560/ZNB.2013-3085 | |
N-(p-tolyl)-1,4-dihydronicotineamide | dichloromethane | N Param.: 7.68 sN Param.: 0.95 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
N-(p-anisyl)-1,4-dihydronicotineamide | dichloromethane | N Param.: 8.11 sN Param.: 0.92 | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 | |
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-(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-(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-(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 | |
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-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-(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-(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 | |
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 | |
N,N-Dimethylbarbituric acid iodonium ylide (in CHCl2) | dichloromethane | N Param.: 7.98 sN Param.: 0.71 | J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768 | |
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 | |
N',N'-dimethylformohydrazide (in MeCN) | MeCN | N Param.: 15.69 sN Param.: 0.51 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
morpholinoisobutylene | dichloromethane | N Param.: 10.04 sN Param.: 0.82 | Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666 | |
morpholine (in water) | water | N Param.: 15.62 sN Param.: 0.54 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
morpholine (in MeCN) | MeCN | N Param.: 15.65 sN Param.: 0.74 | Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925 | |
morpholine (in DMSO) | DMSO | N Param.: 16.96 sN Param.: 0.67 | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
morpholine (in 91M9AN) | MeOH-MeCN mix | N Param.: 15.40 sN Param.: 0.64 | Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542 | |
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 | |
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 | |
methylenecycloundecane | dichloromethane | N Param.: 2.33 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclopropane | dichloromethane | N Param.: -0.47 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclopentane | dichloromethane | N Param.: 2.82 sN Param.: 0.90 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
methylenecyclopentadecane | dichloromethane | N Param.: 1.69 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclooctane | dichloromethane | N Param.: 3.16 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclononane | dichloromethane | N Param.: 2.57 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclohexane | dichloromethane | N Param.: 1.16 sN Param.: 1.04 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
methylenecycloheptane | dichloromethane | N Param.: 2.24 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclododecane | dichloromethane | N Param.: 1.52 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclodecane | dichloromethane | N Param.: 2.82 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methylenecyclobutane | dichloromethane | N Param.: 1.65 sN Param.: 0.90 | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c | |
methyldiphenylsilane | dichloromethane | N Param.: 2.72 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methylamine (in water) | water | N Param.: 13.85 sN Param.: 0.53 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methylamine (in MeCN) | MeCN | N Param.: 15.19 sN Param.: 0.68 | J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g | |
methyl(phenyl)silane | dichloromethane | N Param.: 2.13 sN Param.: 0.73 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methyl(neopentyl)(phenyl)silane | dichloromethane | N Param.: 0.87 sN Param.: 0.75 | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 | |
methyl L-prolinate | MeCN | N Param.: 14.75 sN Param.: 0.82 | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 | |
methyl glycinate (in water) | water | N Param.: 12.08 sN Param.: 0.60 | J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z | |
methyl carbonate (in MeCN) | MeCN | N Param.: 16.03 sN Param.: 0.64 | Eur. J. Org. Chem. 2010, , 4205-4210 10.1002/ejoc.201000414 | |
methyl (cyclohexen-1-yl)prolinate (in MeCN) | MeCN | N Param.: 14.96 sN Param.: 0.68 | Angew. Chem. Int. Ed. 2010, 49, 9526-9529 10.1002/anie.201004344 | |
methoxybis(phenylsulfonyl)methanide (in DMSO) | DMSO | N Param.: 17.29 sN Param.: 0.70 | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 | |
methionine (anionic, in water) | water | N Param.: 13.16 sN Param.: 0.58 | Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h | |
methanolate (in methanol) | MeOH | N Param.: 15.78 sN Param.: 0.56 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
methanolate (in 91M9AN) | MeOH-MeCN mix | N Param.: 14.51 sN Param.: 0.68 | Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170 | |
methanol (in MeCN) | MeCN | N Param.: 6.86 sN Param.: 0.73 | Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360 | |
methanol | MeOH | N Param.: 7.54 sN Param.: 0.92 | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z | |
methanesulfonamide anion (in DMSO) | DMSO | N Param.: 18.61 sN Param.: 0.53 | J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883 | |
MeSO2-CH-CO2Et (in DMSO) | DMSO | N Param.: 18.00 sN Param.: 0.66 | Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455 |