Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
pyrrolidine (in water)	water	N Param.: 17.21 s_N Param.: 0.49	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
pyrrolidine (inMeCN)	MeCN	N Param.: 18.58 s_N Param.: 0.61	J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877
quinidine	dichloromethane	N Param.: 10.54 s_N Param.: 0.74	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
quinine	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	J. Org. Chem. 2009, 74, 7157-7164 10.1021/jo901670w
quinuclidine (in MeCN)	MeCN	N Param.: 20.54 s_N Param.: 0.60	Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489
saccharin anion (in MeCN)	MeCN	N Param.: 10.78 s_N Param.: 0.89	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
Se-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.27 s_N Param.: 0.63	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Se-DHPB (in CH2Cl2)	dichloromethane	N Param.: 15.16 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Se-HBTM (in CH2Cl2)	dichloromethane	N Param.: 14.42 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Se-HyperBTM (in DCM)	dichloromethane	N Param.: 16.11 s_N Param.: 0.58	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Se-HyperBTM (in MeCN)	MeCN	N Param.: 15.84 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Se-HyperBTM (in THF)	THF	N Param.: 14.19 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2025, EarlyView, 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, EarlyView, e202514865 10.1002/anie.202514865
semicarbazide (in water)	water	N Param.: 11.05 s_N Param.: 0.52	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
serine (anionic, in water)	water	N Param.: 13.16 s_N Param.: 0.55	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
SO3(2-) (in water)	water	N Param.: 16.83 s_N Param.: 0.56	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
sodium indenide (in DMSO)	DMSO	N Param.: 23.74 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
styrene	dichloromethane	N Param.: 0.78 s_N Param.: 0.95	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
succinimide anion (in DMSO)	DMSO	N Param.: 16.03 s_N Param.: 0.66	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
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
TCAP (in MeCN)	MeCN	N Param.: 15.60 s_N Param.: 0.68	Chem. Eur. J. 2013, 19, 6435-6442 10.1002/chem.201204452
Te-BTM (in CH2Cl2)	dichloromethane	N Param.: 14.62 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
Te-DHPB (in CH2Cl2)	dichloromethane	N Param.: 16.63 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
tert-butanol (in MeCN)	MeCN	N Param.: 5.35 s_N Param.: 0.72	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
tert-butyl hydrazinecarboxylate (in MeCN)	MeCN	N Param.: 11.40 s_N Param.: 0.70	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
tert-butyl indole-1-carboxylate	MeCN	N Param.: 1.68 s_N Param.: 1.26	J. Am. Chem. Soc. 2013, 135, 6317-6324 10.1021/ja4017655
tert-butyl isocyanide	dichloromethane	N Param.: 5.47 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
tert-butylamine (in MeCN)	MeCN	N Param.: 12.35 s_N Param.: 0.72	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
tert-butylamine (in water)	water	N Param.: 10.48 s_N Param.: 0.65	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
tetra-sec.butylstannane (in 1,2-DCE)	1,2-dichloroethane	N Param.: -1.10 s_N Param.: 1.15	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrabutylstannane	dichloromethane	N Param.: -0.30 s_N Param.: 1.07	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylgermane (in MeCN)	MeCN	N Param.: -4.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylplumbane (in MeCN)	MeCN	N Param.: 0.10 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylsilane	MeCN	N Param.: -6.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylstannane (in 1,2-DCE)	1,2-dichloroethane	N Param.: -1.90 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetraethylstannane (in MeCN)	MeCN	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrahydroborate ion (in water)	water	N Param.: 12.10 s_N Param.: 0.79	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrahydrofuran (in dichloromethane)	dichloromethane	N Param.: -3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tetrahydrothiophene (in CH2Cl2)	dichloromethane	N Param.: 13.10 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
tetrahydrothiophene (in MeCN)	MeCN	N Param.: 13.30 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
tetrahydrothiopyran (in CH2Cl2)	dichloromethane	N Param.: 11.94 s_N Param.: 0.75	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
tetraisobutylstannane	dichloromethane	N Param.: 1.35 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
tetramethylethylene	dichloromethane	N Param.: -1.00 s_N Param.: 1.40	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
tetramisole (TM) (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.68	Angew. Chem. Int. Ed. 2025, EarlyView, e202514865 10.1002/anie.202514865
tetrapropylstannane (in 1,2-DCE)	1,2-dichloroethane	N Param.: -0.50 s_N Param.: 1.13	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
theophylline anion (in water)	water	N Param.: 10.06 s_N Param.: 0.71	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
thioacetate (in MeCN)	MeCN	N Param.: 21.20 s_N Param.: 0.63	Org. Biomol. Chem. 2011, 9, 8046-8050 10.1039/c1ob06245j
thiocyanate (in MeCN)	MeCN	N Param.: 17.94 s_N Param.: 0.60	J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u
thiocyanate (in MeCN)	MeCN	N Param.: 12.13 s_N Param.: 0.60	J. Am. Chem. Soc. 2003, 125, 14126-14132 10.1021/ja037317u
thiophene	dichloromethane	N Param.: -1.01 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
thiophenolate (in DMSO)	DMSO	N Param.: 23.36 s_N Param.: 0.74	J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025
threonine (anionic, in water)	water	N Param.: 12.69 s_N Param.: 0.60	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
thymine anion (in DMSO)	DMSO	N Param.: 17.63 s_N Param.: 0.62	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
thymine anion (in water)	water	N Param.: 11.17 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
toluene	dichloromethane	N Param.: -4.36 s_N Param.: 1.77	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
trans-HMo(CO)2(PCy3)Cp	dichloromethane	N Param.: 6.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trans-HMo(CO)2(PMe3)Cp	dichloromethane	N Param.: 7.80 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trans-HMo(CO)2(PPh3)Cp	dichloromethane	N Param.: 6.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tri-n-butylphosphane	dichloromethane	N Param.: 15.49 s_N Param.: 0.69	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tri-p-tolylmethane	dichloromethane	N Param.: -3.62 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tri-p-tolylmethane (in MeCN)	MeCN	N Param.: -8.80 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tributyl phosphite	dichloromethane	N Param.: 10.36 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
tributylgermane	dichloromethane	N Param.: 5.92 s_N Param.: 0.73	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tributylsilane	dichloromethane	N Param.: 3.99 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
tributylstannane	dichloromethane	N Param.: 9.96 s_N Param.: 0.55	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
tricyclohexylphosphane	dichloromethane	N Param.: 14.64 s_N Param.: 0.68	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triethoxysilane	dichloromethane	N Param.: -1.80 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triethylamine (in CH2Cl2)	dichloromethane	N Param.: 17.30 s_N Param.: 0.52	J. Phys. Org. Chem. 2010, 23, 1029-1035 10.1002/poc.1707
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
triethylgermane	dichloromethane	N Param.: 4.00 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triethylsilane	dichloromethane	N Param.: 3.58 s_N Param.: 0.70	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
trifluoroacetamide anion (in DMSO)	DMSO	N Param.: 15.81 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
trifluoroethanol	TFE	N Param.: 1.11 s_N Param.: 0.96	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
trihexylsilane	dichloromethane	N Param.: 3.89 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triisopropylphosphane	dichloromethane	N Param.: 13.37 s_N Param.: 0.70	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triisopropylsilane	dichloromethane	N Param.: 2.93 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl phosphite (in 91M9AN)	MeOH-MeCN mix	N Param.: 9.04 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
trimethyl(3-(trimethylgermyl)propyl)silane (in MeCN)	MeCN	N Param.: -4.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylplumbyl)propyl)germane (in MeCN)	MeCN	N Param.: -1.00 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylplumbyl)propyl)silane (in MeCN)	MeCN	N Param.: -1.20 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylstannyl)propyl)germane (in MeCN)	MeCN	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(3-(trimethylstannyl)propyl)silane (in MeCN)	MeCN	N Param.: -3.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(4-methylphenethyl)stannane	1,2-dichloroethane	N Param.: -0.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(phenethyl)silane	dichloromethane	N Param.: -3.50 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(phenethyl)stannane	1,2-dichloroethane	N Param.: -1.10 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
trimethyl(prenyl)silane	dichloromethane	N Param.: 0.90 s_N Param.: 1.17	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
trimethylamine (in MeCN)	MeCN	N Param.: 23.05 s_N Param.: 0.45	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
trimethylhydrazine (in MeCN)	MeCN	N Param.: 12.43 s_N Param.: 0.75	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylhydrazine (in MeCN)	MeCN	N Param.: 17.75 s_N Param.: 0.53	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
trimethylsilane	dichloromethane	N Param.: 3.15 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenyl phosphite	dichloromethane	N Param.: 5.51 s_N Param.: 0.76	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triphenylgermane	dichloromethane	N Param.: 3.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
triphenylmethane	dichloromethane	N Param.: -4.27 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
triphenylphosphane	dichloromethane	N Param.: 14.33 s_N Param.: 0.65	Chem. Eur. J. 2005, 11, 917-927 10.1002/chem.200400696
triphenylphosphine (in THF)	THF	N Param.: 13.59 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2011, 50, 6915-6919 10.1002/anie.201102435
triphenylsilane	dichloromethane	N Param.: 2.65 s_N Param.: 0.72	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839