N-Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
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
(F)2-HBTM (in CH2Cl2)	dichloromethane	N Param.: 10.83 s_N Param.: 0.80	ARKIVOC 2024, (4), 202312093 10.24820/ark.5550190[...]
2-methylpyridine (in CH2Cl2)	dichloromethane	N Param.: 10.52 s_N Param.: 0.78	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,6-dimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.87 s_N Param.: 0.68	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
2,4,6-trimethylpyridine (in CH2Cl2)	dichloromethane	N Param.: 9.34 s_N Param.: 0.71	Synthesis 2017, 49, 3495-3504 10.1055/s-0036-1590504
pyridin-4-yl((trifluoromethyl)sulfonyl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 17.88 s_N Param.: 0.73	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
((4-methoxyphenyl)sulfonyl)(pyridin-4-yl)amide (Ph4P+) (in CH2Cl2)	dichloromethane	N Param.: 19.63 s_N Param.: 0.65	J. Am. Chem. Soc. 2025, 147, 5043-5050 10.1021/jacs.4c14825
O-DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.31 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
O-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 13.01 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Te-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
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
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
Se-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.27 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
Se-HBTM (in CH2Cl2)	dichloromethane	N Param.: 14.42 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
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
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
tetramisole (TM) (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
BTM (in CH2Cl2)	dichloromethane	N Param.: 13.06 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
7-F-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.46 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
7-MeO-BTM (in CH2Cl2)	dichloromethane	N Param.: 13.15 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
HBTM (in CH2Cl2)	dichloromethane	N Param.: 13.45 s_N Param.: 0.72	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
Te-HyperBTM (in DCM)	dichloromethane	N Param.: 16.63 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500443 10.1002/ceur.202500443
8-MeO-HyperBTM	dichloromethane	N Param.: 15.70 s_N Param.: 0.63	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-MeO-HyperBTM (in CH2Cl2)	dichloromethane	N Param.: 14.95 s_N Param.: 2.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
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
9-MeS-HyperBTM	dichloromethane	N Param.: 13.49 s_N Param.: 0.78	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
9-Me-HyperBTM	dichloromethane	N Param.: 14.76 s_N Param.: 0.67	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-PivO-HyperBTM	dichloromethane	N Param.: 14.49 s_N Param.: 0.66	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
7-Ms-HyperBTM	dichloromethane	N Param.: 12.52 s_N Param.: 0.75	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperNTM	dichloromethane	N Param.: 14.47 s_N Param.: 0.72	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
HyperPTM	dichloromethane	N Param.: 13.43 s_N Param.: 0.79	ChemistryEurope 2026, 4, e202500434 10.1002/ceur.202500434
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
2,2,2-trifluoroethylamine (in DMSO)	DMSO	N Param.: 12.15 s_N Param.: 0.65	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
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
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
morpholine (in DMSO)	DMSO	N Param.: 16.96 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
piperidine (in DMSO)	DMSO	N Param.: 17.19 s_N Param.: 0.71	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
azide ion (in DMSO)	DMSO	N Param.: 20.50 s_N Param.: 0.59	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
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
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
benzylamine (in DMSO)	DMSO	N Param.: 15.28 s_N 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 s_N Param.: 0.65	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
diethanolamine (in DMSO)	DMSO	N Param.: 15.51 s_N Param.: 0.70	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
ethanolamine (in DMSO)	DMSO	N Param.: 16.07 s_N Param.: 0.61	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
imidazole (in DMSO)	DMSO	N Param.: 11.58 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzimidazole (in DMSO)	DMSO	N Param.: 10.50 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
2-methyl-benzimidazole (in DMSO)	DMSO	N Param.: 10.02 s_N Param.: 0.85	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b