Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
4-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-methoxypyridine (in CH2Cl2)	dichloromethane	N Param.: 13.70 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
diethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.71 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
anion of acetylacetone (in water)	water	N Param.: 13.73 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
phenylsulfinate (in 50W50AN)	water-MeCN mix	N Param.: 13.75 s_N Param.: 0.68	J. Am. Chem. Soc. 2010, 132, 4796-4805 10.1021/ja9102056
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
(4-Br-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.78 s_N Param.: 0.72	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
5-(4-cyanobenzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 13.79 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
bromide (in 50% aq MeCN)	water-MeCN mix	N Param.: 13.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
histidine (anionic, in water)	water	N Param.: 13.83 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
(E)-beta-(N-piperidino)styrene (in MeCN)	MeCN	N Param.: 13.84 s_N Param.: 0.73	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
methylamine (in water)	water	N Param.: 13.85 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(E)-1-styrylpyrrolidine (in MeCN)	MeCN	N Param.: 13.87 s_N Param.: 0.76	Chem. Eur. J. 2018, 24, 5901-5910 10.1002/chem.201705962
anion of Meldrums acid (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
Desoxy Breslow intermediate 2b	THF	N Param.: 13.91 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
anion of 2-nitro-1-phenylethan-1-one (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.76	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of (4-cyanophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.92 s_N Param.: 0.74	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
cumene peroxy anion (in H2O)	water	N Param.: 13.92 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
beta-piperidinium-peroxypropionate	water	N Param.: 13.94 s_N Param.: 0.62	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
(C6H5)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 13.95 s_N Param.: 0.69	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
glutamate (dianionic, in water)	water	N Param.: 13.96 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
2,2-dimethylpyrrolidine	MeCN	N Param.: 13.96 s_N Param.: 0.76	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
[H-B(2,6-F2C6H3)3]- [NEt4]+	MeCN	N Param.: 13.97 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
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-(triphenylsilyl)pyrrolidine	MeCN	N Param.: 14.00 s_N Param.: 0.84	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
anion of nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.02 s_N Param.: 0.61	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
1,3-diaminopropane (in water)	water	N Param.: 14.02 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
1-(N-piperidino)cyclohexene (in MeCN)	MeCN	N Param.: 14.02 s_N Param.: 0.76	J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x
anion of (4-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.05 s_N Param.: 0.72	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
1,3,4-triphenyl-1H-1,2,4-triazol-4-ium-5-ide (in THF)	THF	N Param.: 14.07 s_N Param.: 0.84	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
peroxy-beta-alanate	water	N Param.: 14.07 s_N Param.: 0.56	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN)	MeCN	N Param.: 14.09 s_N Param.: 0.66	Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634
chloride (in 50/50 MeOH/MeCN)	MeOH-MeCN mix	N Param.: 14.10 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
2,3,4,6,7,8-hexahydropyrimido[2,1-b][1,3]thiazine	dichloromethane	N Param.: 14.10 s_N Param.: 0.82	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
N-methylhydroxylamine (in MeCN)	MeCN	N Param.: 14.10 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
phenylalanine (anionic, in water)	water	N Param.: 14.12 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
[H-B(2,4,6-F3C6H2)3]- [NEt4]+	MeCN	N Param.: 14.13 s_N Param.: 0.61	Angew. Chem. Int. Ed. 2015, 54, 14508-14512 10.1002/anie.201507298
2-Bz super-dmap (in MeCN)	MeCN	N Param.: 14.19 s_N Param.: 0.67	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
2-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.24 s_N Param.: 0.82	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
anion of (3-nitrophenyl)nitromethane (in water)	water	N Param.: 14.25 s_N Param.: 0.46	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
tris(2-methoxyphenyl)phosphane	dichloromethane	N Param.: 14.26 s_N Param.: 0.73	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
4-methoxyaniline (in water)	water	N Param.: 14.28 s_N Param.: 0.68	ChemPlusChem 2015, 80, 1673-1679 10.1002/cplu.201500246
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
t-butylperoxy anion (in H2O)	water	N Param.: 14.29 s_N Param.: 0.51	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
ethyl glycinate (in DMSO)	DMSO	N Param.: 14.30 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
p-methylphenolate (in H2O)	water	N Param.: 14.30 s_N Param.: 0.55	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
p-nitrophenolate (in DMSO)	DMSO	N Param.: 14.32 s_N Param.: 0.77	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
triphenylphosphane	dichloromethane	N Param.: 14.33 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
anion of 3-methyl acetylacetone (in water)	water	N Param.: 14.33 s_N Param.: 0.69	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
peroxy-GABA	water	N Param.: 14.33 s_N Param.: 0.57	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
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
allylamine (in MeCN)	MeCN	N Param.: 14.37 s_N Param.: 0.66	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
2-aminobutan-1-ol (in DMSO)	DMSO	N Param.: 14.39 s_N Param.: 0.67	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
(Z)-1-(1,3-dimesityl-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in DMSO)	DMSO	N Param.: 14.40 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)	THF	N Param.: 14.40 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524
peroxomonosulfate (in water)	water	N Param.: 14.41 s_N Param.: 0.60	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
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-methyl-1,4,5,6-tetrahydropyrimidine (in MeCN)	MeCN	N Param.: 14.43 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
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
NaB(OAc)3H (in DMSO)	DMSO	N Param.: 14.45 s_N Param.: 0.76	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
THTP (3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 14.45 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
Desoxy Breslow intermediate 2a'	THF	N Param.: 14.45 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
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
(4-MeO-C6H4)-(CO)-CH=SMe2 (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.71	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
5-(4-(dimethylamino)benzyl)-2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ide (in DMSO)	DMSO	N Param.: 14.48 s_N Param.: 0.86	Chem. Eur. J. 2014, 20, 11069-11077 10.1002/chem.201403161
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 14.49 s_N Param.: 0.86	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
bromide (in 80% aq EtOH)	water-EtOH mix	N Param.: 14.50 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
methanolate (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.51 s_N Param.: 0.68	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
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
2-methyl-1,4,5,6-tetrahydropyrimidine (in DMSO)	DMSO	N Param.: 14.58 s_N Param.: 0.79	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
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
2-phenyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.72	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
tricyclohexylphosphane	dichloromethane	N Param.: 14.64 s_N Param.: 0.68	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
chloride (in EtOH)	EtOH	N Param.: 14.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
NaBH4 (in DMSO)	DMSO	N Param.: 14.74 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
anion of (3-nitrophenyl)nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.75 s_N Param.: 0.71	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
methyl L-prolinate	MeCN	N Param.: 14.75 s_N Param.: 0.82	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
4-pyridone anion (in water)	water	N Param.: 14.76 s_N Param.: 0.48	J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
theophylline anion (in DMSO)	DMSO	N Param.: 14.78 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
4-(dimethylamino)pyridine (in DMSO)	DMSO	N Param.: 14.80 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(morpholino)pyridine (in MeCN)	MeCN	N Param.: 14.80 s_N Param.: 0.63	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
4-nitro-imidazole anion (in DMSO)	DMSO	N Param.: 14.81 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
tris(2,4-dimethylphenyl)phosphane	dichloromethane	N Param.: 14.88 s_N Param.: 0.41	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
4-(dimethylamino)pyridine (in DMF)	DMF	N Param.: 14.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
3,5-dinitrobenzoate (in MeCN)	MeCN	N Param.: 14.90 s_N Param.: 0.71	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
1,3-diethyl-thiobarbiturate anion (in DMSO)	DMSO	N Param.: 14.90 s_N Param.: 0.80	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
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
Bu4NBH4 (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.79	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
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