Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
bromide (in 40% aq MeCN)	water-MeCN mix	N Param.: 12.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
bromide (in 50% aq EtOH)	water-EtOH mix	N Param.: 13.60 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
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
bromide (in CF3CH2OH)	TFE	N Param.: 11.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
bromide (in H2O)	water	N Param.: 11.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
bromite (in water)	water	N Param.: 12.75 s_N Param.: 0.59	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
bromo(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 23.90 s_N Param.: 0.62	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
bromoborane-triethylamine-complex	dichloromethane	N Param.: 7.49 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
BTM (in CH2Cl2)	dichloromethane	N Param.: 13.06 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2025, 64, e202514865 10.1002/anie.202514865
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
buta-1,3-diene	dichloromethane	N Param.: -0.87 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
butyltrimethylsilane	dichloromethane	N Param.: -5.40 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
chloride (in 20% aq MeCN)	water-MeCN mix	N Param.: 11.31 s_N Param.: 0.58	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 40% aq MeCN)	water-MeCN mix	N Param.: 11.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 50% aq EtOH)	water-EtOH mix	N Param.: 11.80 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 50% aq MeCN)	water-MeCN mix	N Param.: 12.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
chloride (in 60% aq MeCN)	water-MeCN mix	N Param.: 12.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in 80% aq MeCN)	water-MeCN mix	N Param.: 13.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in CF3CH2OH)	TFE	N Param.: 10.30 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in EtOH)	EtOH	N Param.: 14.70 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in H2O)	water	N Param.: 10.10 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in hexafluoroisopropanol)	HFIP	N Param.: 8.00 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in MeCN)	MeCN	N Param.: 17.20 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloride (in MeOH)	MeOH	N Param.: 12.90 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO)	DMSO	N Param.: 26.90 s_N Param.: 0.45	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO)	DMSO	N Param.: 25.59 s_N Param.: 0.51	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO)	DMSO	N Param.: 24.88 s_N Param.: 0.49	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
chloro(phenylsulfonyl)methanide (in DMF)	DMF	N Param.: 26.64 s_N Param.: 0.64	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
chloro(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 28.27 s_N Param.: 0.42	J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844
chlorodimethylsilane	dichloromethane	N Param.: 0.79 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cis-HMn(PCy3)(CO)4	dichloromethane	N Param.: 2.20 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cis-HMn(PPh3)(CO)4	dichloromethane	N Param.: 2.30 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cis-HRe(PPh3)(CO)4	dichloromethane	N Param.: 4.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Cp2Ti(CH2Ph)2 - Dibenzyltitanocene	dichloromethane	N Param.: 4.38 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Cp2Zr(CH2Ph)2 - Dibenzylzirconocene	dichloromethane	N Param.: 5.10 s_N Param.: 1.03	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Cp2Zr(Me)2 - Dimethylzirconocene	dichloromethane	N Param.: 4.35 s_N Param.: 1.09	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
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
cyanamide anion (in DMSO)	DMSO	N Param.: 20.33 s_N Param.: 0.64	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
cyanate (in MeCN)	MeCN	N Param.: 13.60 s_N Param.: 0.84	Chem. Eur. J. 2008, 14, 3866-3868 10.1002/chem.200800314
cyanide (in MeCN)	MeCN	N Param.: 16.27 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2005, 44, 142-145 10.1002/anie.200461640
cyano((diphenylmethylene)amino)methanide	DMSO	N Param.: 29.50 s_N Param.: 0.50	Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...]
cyano(pyridin-1-ium-1-yl)methanide (in DMSO)	DMSO	N Param.: 25.94 s_N Param.: 0.42	J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h
cyanoborate ion (in water)	water	N Param.: 9.99 s_N Param.: 0.54	Org. Biomol. Chem. 2023, 21, 85-88 10.1039/D2OB02041F
cyclohepta-1,3,5-trienyl-Fe(CO)3	dichloromethane	N Param.: 3.42 s_N Param.: 0.94	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
cyclohepta-1,3-diene	dichloromethane	N Param.: 0.06 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cycloheptatriene	dichloromethane	N Param.: 0.52 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538
cycloheptatriene (in MeCN)	MeCN	N Param.: 0.55 s_N Param.: 0.97	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cyclohexa-1,3-diene	dichloromethane	N Param.: 0.67 s_N Param.: 1.10	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
cyclopentadiene	dichloromethane	N Param.: 2.30 s_N Param.: 1.06	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclopentene	dichloromethane	N Param.: -1.55 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cysteine (dianionic, in water, S-nucleophile!)	water	N Param.: 23.43 s_N Param.: 0.42	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
DABCO (in MeCN)	MeCN	N Param.: 18.80 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2007, 46, 6176-6179 10.1002/anie.200701489
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
DBN (in CH2Cl2)	dichloromethane	N Param.: 15.50 s_N Param.: 0.76	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
DBN (in MeCN)	MeCN	N Param.: 16.28 s_N Param.: 0.67	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
DBU (in MeCN)	MeCN	N Param.: 15.29 s_N Param.: 0.70	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
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
Desoxy Breslow intermediate 2a	THF	N Param.: 17.12 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2a	DMSO	N Param.: 17.41 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
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
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
Desoxy Breslow intermediate 2b'	THF	N Param.: 11.42 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Desoxy Breslow intermediate 2c'	THF	N Param.: 12.75 s_N Param.: 0.71	Angew. Chem. Int. Ed. 2012, 51, 6231-6235 10.1002/anie.201202327
Dexoxy Breslow intermediate 6	THF	N Param.: 15.58 s_N Param.: 0.57	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
DHPB (in CH2Cl2)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
di(methoxyethyl)amine (in MeCN)	MeCN	N Param.: 13.24 s_N Param.: 0.93	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diazocyclopentadiene (in CH2Cl2)	dichloromethane	N Param.: 4.84 s_N Param.: 1.06	Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
dibutylsulfide (in CH2Cl2)	dichloromethane	N Param.: 11.86 s_N Param.: 0.74	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
dichloro(methyl)silane	dichloromethane	N Param.: -3.20 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
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
diethanolamine (in DMSO)	DMSO	N Param.: 15.51 s_N Param.: 0.70	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
diethanolamine (in water)	water	N Param.: 13.00 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
diethyl diazomalonate	dichloromethane	N Param.: -0.35 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diethyl(methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
diethylether (in dichloromethane)	dichloromethane	N Param.: -5.10 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethylmercury (in MeCN)	MeCN	N Param.: -0.70 s_N Param.: 1.10	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dihexylsilane	dichloromethane	N Param.: 2.27 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Dimedone iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 6.18 s_N Param.: 0.81	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
dimethoxymethane	dichloromethane	N Param.: -4.90 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
Dimethyl 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
Dimethyl bis(indenyl)zirconium(IV)	dichloromethane	N Param.: 6.89 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
dimethyl diazomalonate	dichloromethane	N Param.: -1.24 s_N Param.: 0.81	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
dimethyl((trimethylgermyl)methyl)silane	dichloromethane	N Param.: 5.36 s_N Param.: 0.62	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl((trimethylstannyl)methyl)silane	dichloromethane	N Param.: 6.53 s_N Param.: 0.58	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(neopentyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(p-tolyl)silane	dichloromethane	N Param.: 3.83 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(phenyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethyl(propoxy)silane	dichloromethane	N Param.: 2.40 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dimethylselenide (in CH2Cl2)	dichloromethane	N Param.: 12.60 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977