N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
7-MeS-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7,8,9-(MeO)3-HyperBTM	dichloromethane	N Param.: 14.62 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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
9-Me-HyperBTM	dichloromethane	N Param.: 14.76 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
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
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
7-MeO-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.95 s_N Param.: 2.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.96 s_N Param.: 0.64	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(pyrrolidin-2-ylmethyl)thiourea	MeCN	N Param.: 14.97 s_N Param.: 0.69	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
4-pyrrolidinopyridine (in MeCN)	MeCN	N Param.: 14.99 s_N Param.: 0.69	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
azide ion (in 45M55AN)	MeOH-MeCN mix	N Param.: 15.01 s_N Param.: 0.80	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
purine anion (in DMSO)	DMSO	N Param.: 15.03 s_N Param.: 0.77	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
n-propylamine (in MeCN)	MeCN	N Param.: 15.11 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
Se-DHPB (in CH2Cl2)	dichloromethane	N Param.: 15.16 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
methylamine (in MeCN)	MeCN	N Param.: 15.19 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
4-aminopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.20 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
(S)-N-propylpyrrolidine-2-carboxamide	MeCN	N Param.: 15.20 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-methyl-1,4,5,6-tetrahydropyrimidine (in CH2Cl2)	dichloromethane	N Param.: 15.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2013, , 3369-3377 10.1002/ejoc.201300213
Se-tetramisole (Se-TM) (in CH2Cl2)	dichloromethane	N Param.: 15.26 s_N Param.: 0.60	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
n-butylamine (in MeCN)	MeCN	N Param.: 15.27 s_N Param.: 0.63	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
benzylamine (in DMSO)	DMSO	N Param.: 15.28 s_N Param.: 0.65	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
DBU (in MeCN)	MeCN	N Param.: 15.29 s_N Param.: 0.70	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
(R)-2-benzhydryl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 15.30 s_N Param.: 0.55	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-4-phenyl-1-(pyrrolidin-2-ylmethyl)-1H-1,2,3-triazole	MeCN	N Param.: 15.32 s_N Param.: 0.72	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-Ac super-dmap (in MeCN)	MeCN	N Param.: 15.39 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
morpholine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.40 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
(S)-2-(azidomethyl)pyrrolidine	MeCN	N Param.: 15.43 s_N Param.: 0.73	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
1-aminopropan-2-ol (in DMSO)	DMSO	N Param.: 15.47 s_N Param.: 0.65	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
DBN (in CH2Cl2)	dichloromethane	N Param.: 15.50 s_N Param.: 0.76	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
4-(dimethylamino)pyridine (in MeCN)	MeCN	N Param.: 15.51 s_N Param.: 0.62	J. Phys. Chem. A 2012, 116, 8494-8499 10.1021/jp3049247
diethanolamine (in DMSO)	DMSO	N Param.: 15.51 s_N Param.: 0.70	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
phthalimide anion (in DMSO)	DMSO	N Param.: 15.52 s_N Param.: 0.67	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
(S)-1-(pyrrolidin-2-ylmethyl)-1H-imidazole	MeCN	N Param.: 15.55 s_N Param.: 0.69	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
TCAP (in MeCN)	MeCN	N Param.: 15.60 s_N Param.: 0.68	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
morpholine (in water)	water	N Param.: 15.62 s_N Param.: 0.54	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
piperidine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.63 s_N Param.: 0.64	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
morpholine (in MeCN)	MeCN	N Param.: 15.65 s_N Param.: 0.74	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
2-(naphthylmethyl)quinuclidine (in MeCN)	MeCN	N Param.: 15.66 s_N Param.: 0.62	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
N',N'-dimethylformohydrazide (in MeCN)	MeCN	N Param.: 15.69 s_N Param.: 0.51	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
n-propylamine (in DMSO)	DMSO	N Param.: 15.70 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
N-methyl-trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.70 s_N Param.: 0.71	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
1-methyl-2-phenylpyrrolidine (in MeCN)	MeCN	N Param.: 15.70 s_N Param.: 0.54	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
8-MeO-HyperBTM	dichloromethane	N Param.: 15.70 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
4-(dimethylamino)pyridine (in CH2Cl2)	dichloromethane	N Param.: 15.80 s_N Param.: 0.66	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.81 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
Se-HyperBTM (in MeCN)	MeCN	N Param.: 15.84 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
4-pyrrolidinopyridine (in CH2Cl2)	dichloromethane	N Param.: 15.90 s_N Param.: 0.67	Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941
4-(dimethylamino)pyridine (in THF)	THF	N Param.: 15.90 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
(S)-2-(pyrrolidin-2-ylmethyl)isoindoline-1,3-dione	MeCN	N Param.: 15.90 s_N Param.: 0.77	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
pyrrolidine (in 91M9AN)	MeOH-MeCN mix	N Param.: 15.97 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
ethyl N-acetylcarbamate anion (in DMSO)	DMSO	N Param.: 15.99 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
succinimide anion (in DMSO)	DMSO	N Param.: 16.03 s_N Param.: 0.66	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
2-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.06 s_N Param.: 0.68	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
ethanolamine (in DMSO)	DMSO	N Param.: 16.07 s_N Param.: 0.61	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
Se-HyperBTM (in DCM)	dichloromethane	N Param.: 16.11 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
DBU (in THF)	THF	N Param.: 16.12 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
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
1,2-dimethylhydrazine (in MeCN)	MeCN	N Param.: 16.15 s_N Param.: 0.68	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
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
(S)-diphenyl(pyrrolidin-2-yl)methanol	MeCN	N Param.: 16.18 s_N Param.: 0.56	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
DBN (in MeCN)	MeCN	N Param.: 16.28 s_N Param.: 0.67	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
benzotriazole anion (in DMSO)	DMSO	N Param.: 16.29 s_N Param.: 0.65	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
azide ion (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.30 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
1-methyl uracil anion (in DMSO)	DMSO	N Param.: 16.36 s_N Param.: 0.69	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 16.38 s_N Param.: 0.60	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
4-formyl-imidazole anion (in DMSO)	DMSO	N Param.: 16.40 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
(R)-2-isopropylpyrrolidine	MeCN	N Param.: 16.44 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4P+) (in MeCN)	MeCN	N Param.: 16.48 s_N Param.: 0.60	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
N-methyl-morpholine (in CH2Cl2)	dichloromethane	N Param.: 16.50 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
(R)-2-isopropyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine	dichloromethane	N Param.: 16.50 s_N Param.: 0.48	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
(S)-2-(methoxymethyl)pyrrolidine	MeCN	N Param.: 16.50 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
(S)-2-benzhydrylpyrrolidine	MeCN	N Param.: 16.61 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
Te-DHPB (in CH2Cl2)	dichloromethane	N Param.: 16.63 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Te-HyperBTM (in DCM)	dichloromethane	N Param.: 16.63 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500443 10.1002/ceur.202500443
2-Me super-dmap (in MeCN)	MeCN	N Param.: 16.65 s_N Param.: 0.58	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Bu4N+) (in MeCN)	MeCN	N Param.: 16.68 s_N Param.: 0.59	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
azide ion (in 91nPr9AN)	nPrOH-MeCN mix	N Param.: 16.70 s_N Param.: 0.73	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
(S)-pyrrolidin-2-ylmethanol	MeCN	N Param.: 16.74 s_N Param.: 0.67	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
2-methylpyrrolidine (in MeCN)	MeCN	N Param.: 16.78 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
N-methyl-morpholine (in MeCN)	MeCN	N Param.: 16.80 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
1-methyl-2-phenylpyrrolidine (in CH2Cl2)	dichloromethane	N Param.: 16.80 s_N Param.: 0.49	J. Phys. Org. Chem. 2016, 29, 759-767 10.1002/poc.3580
2-Et super-dmap (in MeCN)	MeCN	N Param.: 16.81 s_N Param.: 0.60	Org. Lett. 2011, 13, 530-533 10.1021/ol1029589
morpholine (in DMSO)	DMSO	N Param.: 16.96 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
uracil anion (in DMSO)	DMSO	N Param.: 17.04 s_N Param.: 0.63	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
azide ion (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.07 s_N Param.: 0.71	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
triethylamine (in MeCN)	MeCN	N Param.: 17.10 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
p-toluenesulfonamide anion (in DMSO)	DMSO	N Param.: 17.14 s_N Param.: 0.60	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
piperidine (in DMSO)	DMSO	N Param.: 17.19 s_N Param.: 0.71	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
pyridin-4-yl(tosyl)amide (Ph4P+) (in MeCN)	MeCN	N Param.: 17.19 s_N Param.: 0.64	J. Org. Chem. 2025, 90, 2298-2306 10.1021/acs.joc.4c02668
nitrite ion (in MeCN)	MeCN	N Param.: 17.20 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2005, 44, 4623-4626 10.1002/anie.200501274