Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
2-(pyrid-4-yl)CH(-)CO2Et (in DMSO)	DMSO	N Param.: 23.27 s_N Param.: 0.70	Eur. J. Org. Chem. 2013, , 4255-4261 10.1002/ejoc.201300265
4-(2-(fluorodiphenylmethyl)pyrrolidin-1-yl)pyridine	dichloromethane	N Param.: 14.57 s_N Param.: 0.75	Eur. J. Org. Chem. 2014, , 1202-1211 10.1002/ejoc.201301730
1-ethoxy-2-methyl-1,3-dioxobutan-2-ide (in DMSO)	DMSO	N Param.: 19.58 s_N Param.: 0.73	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclopentan-1-ide (in DMSO)	DMSO	N Param.: 18.63 s_N Param.: 0.82	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclohexan-1-ide (in DMSO)	DMSO	N Param.: 18.32 s_N Param.: 0.84	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocycloheptan-1-ide	DMSO	N Param.: 19.53 s_N Param.: 0.83	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclooctan-1-ide (in DMSO)	DMSO	N Param.: 20.02 s_N Param.: 0.76	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
1-(ethoxycarbonyl)-2-oxocyclododecan-1-ide (in DMSO)	DMSO	N Param.: 20.60 s_N Param.: 0.63	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
3-methyl-2,4-dioxotetrahydro-2H-pyran-3-ide (in DMSO)	DMSO	N Param.: 14.46 s_N Param.: 0.91	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
3-acetyl-2-oxotetrahydro-2H-pyran-3-ide (in DMSO)	DMSO	N Param.: 17.00 s_N Param.: 0.74	Eur. J. Org. Chem. 2015, , 7594-7601 10.1002/ejoc.201501107
anion of diethyl 2-(isopropyl)malonate (in DMSO)	DMSO	N Param.: 18.74 s_N Param.: 0.71	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-butylmalonate (in DMSO)	DMSO	N Param.: 23.00 s_N Param.: 0.55	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-cyclohexylmalonate (in DMSO)	DMSO	N Param.: 19.23 s_N Param.: 0.67	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-phenylmalonate (in DMSO)	DMSO	N Param.: 15.93 s_N Param.: 0.99	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.96	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of triethyl methanetricarboxylate (in DMSO)	DMSO	N Param.: 15.33 s_N Param.: 0.72	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(acetyl)malonate (in DMSO)	DMSO	N Param.: 13.83 s_N Param.: 0.84	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(benzoyl)malonate (in DMSO)	DMSO	N Param.: 13.63 s_N Param.: 0.80	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of 5-phenyl Meldrum's acid (in DMSO)	DMSO	N Param.: 11.54 s_N Param.: 0.95	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)	DMSO	N Param.: 12.35 s_N Param.: 0.90	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(p-anisyl)malonate (in DMSO)	DMSO	N Param.: 16.73 s_N Param.: 0.91	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
4-(morpholino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 14.59 s_N Param.: 0.69	Eur. J. Org. Chem. 2016, , 4050-4058 10.1002/ejoc.201600572
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 1.04	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 2-phenylmalononitrile (in DMSO)	DMSO	N Param.: 15.58 s_N Param.: 1.00	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 2-phenyl-2-(phenylsulfonyl)acetonitrile (in DMSO)	DMSO	N Param.: 15.97 s_N Param.: 0.72	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of (phenylmethylenedisulfonyl)dibenzene (in DMSO)	DMSO	N Param.: 15.07 s_N Param.: 0.79	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of 1,2,3-triphenylpropane-1,3-dione (in DMSO)	DMSO	N Param.: 14.99 s_N Param.: 0.83	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
beta-piperidinium-peroxypropionate	water	N Param.: 13.94 s_N Param.: 0.62	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-beta-alanate	water	N Param.: 14.07 s_N Param.: 0.56	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
3-diazoindolin-2-one	dichloromethane	N Param.: 3.16 s_N Param.: 1.03	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindan-1-one	dichloromethane	N Param.: 5.61 s_N Param.: 0.65	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazocyclohexanone	dichloromethane	N Param.: 3.44 s_N Param.: 0.83	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-tetralone	dichloromethane	N Param.: 3.51 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazoindandione	dichloromethane	N Param.: 0.16 s_N Param.: 0.86	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazo-1-benzosuberone	dichloromethane	N Param.: 2.72 s_N Param.: 0.96	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
2-diazobenzothiophen-3(2H)-one	dichloromethane	N Param.: 0.40 s_N Param.: 0.93	Eur. J. Org. Chem. 2023, 26, e202300005 10.1002/ejoc.202300005
1,3,5-trimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 21.16 s_N Param.: 0.59	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.91 s_N Param.: 0.62	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1,3-dimethyl-2-methylene-1,2-dihydropyridine (in MeCN)	MeCN	N Param.: 19.69 s_N Param.: 0.61	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1,6-dimethyl-2-methylene-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 20.76 s_N Param.: 0.60	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1-methyl-2-methylene-3-phenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.41 s_N Param.: 0.61	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
1-(4-(tert-butyl)phenyl)-2-methylene-4,6-diphenyl-1,2-dihydropyridine (in DMSO)	DMSO	N Param.: 19.36 s_N Param.: 0.68	Eur. J. Org. Chem. 2024, 27, e202400373 10.1002/ejoc.202400373
4-methoxyaniline (in water)	water	N Param.: 14.28 s_N Param.: 0.68	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
2-phenylethylamine (in water)	water	N Param.: 13.40 s_N Param.: 0.57	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 13.58 s_N Param.: 0.77	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2-benzyl-1,1,3,3-tetramethylguanidine	dichloromethane	N Param.: 14.36 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1,3-dimethylimidazolidin-2-imine	dichloromethane	N Param.: 12.46 s_N Param.: 0.87	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
N-(1,3-dimethylimidazolidin-2-ylidene)-1-phenylmethanamine	dichloromethane	N Param.: 14.00 s_N Param.: 0.70	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole (TBO)	dichloromethane	N Param.: 14.44 s_N Param.: 0.79	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyrimidine (TBN)	dichloromethane	N Param.: 16.15 s_N Param.: 0.73	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine (MeTBD)	dichloromethane	N Param.: 14.43 s_N Param.: 0.81	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine	dichloromethane	N Param.: 16.16 s_N Param.: 0.75	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
DBN (in CH2Cl2)	dichloromethane	N Param.: 15.50 s_N Param.: 0.76	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
(5-methyl-furan-2-yl) pinacol boronate	MeCN	N Param.: 2.90 s_N Param.: 0.98	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MDA boronate	MeCN	N Param.: 6.38 s_N Param.: 0.86	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) MIDA boronate	MeCN	N Param.: 1.84 s_N Param.: 1.26	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl) trifluoroborate	MeCN	N Param.: 7.66 s_N Param.: 1.04	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
tetrakis(5-methyl-furan-2-yl)borate	MeCN	N Param.: 9.09 s_N Param.: 1.12	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
(5-methyl-furan-2-yl)(1,1,1-tris(methoxy)ethane)borate	MeCN	N Param.: 12.55 s_N Param.: 0.92	Chem. Sci. 2012, 3, 878-882 10.1039/c2sc00883a
phenylsilane	dichloromethane	N Param.: 0.06 s_N Param.: 0.71	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylsilane	dichloromethane	N Param.: 2.65 s_N Param.: 0.72	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(phenyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(N-pyrrolidino)cyclopentene	dichloromethane	N Param.: 15.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-piperidino)cyclopentene	dichloromethane	N Param.: 15.06 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-pyrrolidino)cyclohexene	dichloromethane	N Param.: 14.91 s_N Param.: 0.86	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(N-morpholino)cyclopentene	dichloromethane	N Param.: 13.41 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylmethylamino)cyclopentene	dichloromethane	N Param.: 12.90 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(phenylmethylamino)cyclohexene	dichloromethane	N Param.: 10.73 s_N Param.: 0.81	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
morpholinoisobutylene	dichloromethane	N Param.: 10.04 s_N Param.: 0.82	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
N-(triisopropylsilyl)pyrrole	dichloromethane	N Param.: 3.12 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-(1-cyclohexenyl)-4-methylpiperazine	dichloromethane	N Param.: 12.51 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(Z)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.26 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(E)-1-(N-morpholino)propene	dichloromethane	N Param.: 12.06 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
1-methyl-4-(N-morpholino)tetrahydropyridine	dichloromethane	N Param.: 12.03 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
(E)-beta-(N-morpholino)styrene	dichloromethane	N Param.: 10.76 s_N Param.: 0.87	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
alpha-(N-morpholino)styrene	dichloromethane	N Param.: 9.96 s_N Param.: 0.79	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(dimethylamino)acrylate	dichloromethane	N Param.: 9.43 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(N-morpholino)acrylate	dichloromethane	N Param.: 8.52 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
pyrrole	dichloromethane	N Param.: 4.63 s_N Param.: 1.00	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
triphenylphosphane	dichloromethane	N Param.: 14.33 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
phenyldiazomethane	dichloromethane	N Param.: 9.35 s_N Param.: 0.83	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
(trimethylsilyl)diazomethane	dichloromethane	N Param.: 8.97 s_N Param.: 0.75	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
ethyl diazoacetate	dichloromethane	N Param.: 4.91 s_N Param.: 0.95	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diethyl diazomalonate	dichloromethane	N Param.: -0.35 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
tris(4-chlorophenyl)phosphane	dichloromethane	N Param.: 12.58 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tris(4-methylphenyl)phosphane	dichloromethane	N Param.: 15.44 s_N Param.: 0.64	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tris(4-methoxyphenyl)phosphane	dichloromethane	N Param.: 16.17 s_N Param.: 0.62	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tris(4-dimethylaminophenyl)phosphane	dichloromethane	N Param.: 18.39 s_N Param.: 0.64	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triisopropylphosphane	dichloromethane	N Param.: 13.37 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tricyclohexylphosphane	dichloromethane	N Param.: 14.64 s_N Param.: 0.68	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tri-n-butylphosphane	dichloromethane	N Param.: 15.49 s_N Param.: 0.69	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triphenyl phosphite	dichloromethane	N Param.: 5.51 s_N Param.: 0.76	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tributyl phosphite	dichloromethane	N Param.: 10.36 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
4-chloropyridine (in CH2Cl2)	dichloromethane	N Param.: 11.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-chloropyridine (in H2O)	water	N Param.: 10.50 s_N Param.: 0.73	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941