Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
tetraethylstannane (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)germane (in MeCN)	MeCN	N Param.: -2.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
4,5-dimethyl-1,3-dioxolane (anti)	dichloromethane	N Param.: -2.40 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2-ethyl-4,5-dimethyl-1,3-dioxolane (syn)	dichloromethane	N Param.: -2.40 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bis(4-methoxyphenyl)methane (in CH2Cl2)	dichloromethane	N Param.: -2.11 s_N Param.: 0.98	J. Am. Chem. Soc. 2014, 136, 13863-13873 10.1021/ja507598y
1,1-dimethylsiletane	dichloromethane	N Param.: -2.10 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1% water/99% HFIP (w/w)	water-HFIP mix	N Param.: -1.93 s_N Param.: 1.09	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
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
triethoxysilane	dichloromethane	N Param.: -1.80 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
(4-chlorophenethyl)trimethylstannane	1,2-dichloroethane	N Param.: -1.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1,3-bis(trimethylstannyl)propane (in MeCN)	MeCN	N Param.: -1.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
2% water/98% HFIP (w/w)	water-HFIP mix	N Param.: -1.62 s_N Param.: 1.10	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
cyclopentene	dichloromethane	N Param.: -1.55 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-(trimethylsilyl)propene	dichloromethane	N Param.: -1.46 s_N Param.: 1.05	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
dimethyl diazomalonate	dichloromethane	N Param.: -1.24 s_N Param.: 0.81	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
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
3% water/97% HFIP (w/w)	water-HFIP mix	N Param.: -1.19 s_N Param.: 1.08	J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064
anisole	dichloromethane	N Param.: -1.18 s_N Param.: 1.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
alpha-(trimethylsilyl)styrene	dichloromethane	N Param.: -1.13 s_N Param.: 1.46	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)6	dichloromethane	N Param.: -1.11 s_N Param.: 0.92	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
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
(Z)-phenylpropene	dichloromethane	N Param.: -1.07 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
2-propyl-1,3-dioxolane	dichloromethane	N Param.: -1.06 s_N Param.: 0.81	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
thiophene	dichloromethane	N Param.: -1.01 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
tetramethylethylene	dichloromethane	N Param.: -1.00 s_N Param.: 1.40	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
2-phenyldioxolane	dichloromethane	N Param.: -0.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3(C5H4CO2Me)	dichloromethane	N Param.: -0.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
3-propylcyclopentene	dichloromethane	N Param.: -0.88 s_N Param.: 0.94	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
buta-1,3-diene	dichloromethane	N Param.: -0.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
9,10-dihydroanthracene	dichloromethane	N Param.: -0.86 s_N Param.: 0.92	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
2-(trimethylsilyl)thiophene	dichloromethane	N Param.: -0.80 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(2-([1,1'-biphenyl]-4-yl)ethyl)trimethylstannane	1,2-dichloroethane	N Param.: -0.80 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
4-(trimethylsilyl)but-1-en-3-ynyl-Co2(CO)5(PPh3)	dichloromethane	N Param.: -0.76 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
(E,E)-2,5-heptadiene	dichloromethane	N Param.: -0.74 s_N Param.: 0.99	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
4-methyl-2,5-heptadiene	dichloromethane	N Param.: -0.73 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
diethylmercury (in MeCN)	MeCN	N Param.: -0.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
1-(p-tolyl)-1-(trimethylsilyl)ethene	dichloromethane	N Param.: -0.65 s_N Param.: 1.59	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane (in CH2Cl2)	dichloromethane	N Param.: -0.64 s_N Param.: 1.10	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
allylchlorodimethylsilane	dichloromethane	N Param.: -0.57 s_N Param.: 1.06	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
(2-methylallyl)trichlorosilane	dichloromethane	N Param.: -0.57 s_N Param.: 0.95	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cycloocta-1,3-diene	dichloromethane	N Param.: -0.50 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
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
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
(E)-propenylbenzene	dichloromethane	N Param.: -0.49 s_N Param.: 1.18	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
methylenecyclopropane	dichloromethane	N Param.: -0.47 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
1-ethinylcyclohexenyl-Co2(CO)6	dichloromethane	N Param.: -0.44 s_N Param.: 1.06	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
beta-(trimethylsilyl)styrene	dichloromethane	N Param.: -0.43 s_N Param.: 1.06	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
diethyl diazomalonate	dichloromethane	N Param.: -0.35 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913