Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
anion of nitromethane (in water)	water	N Param.: 12.06 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.58 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of p-tolylnitromethane (in DMSO)	DMSO	N Param.: 18.31 s_N Param.: 0.76	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of p-tolylnitromethane (in water)	water	N Param.: 13.09 s_N Param.: 0.50	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of phenylnitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.51 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of phenylnitromethane (in DMSO)	DMSO	N Param.: 18.29 s_N Param.: 0.71	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of phenylnitromethane (in H2O)	water	N Param.: 12.05 s_N Param.: 0.53	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of triethyl methanetricarboxylate (in DMSO)	DMSO	N Param.: 15.33 s_N Param.: 0.72	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anisole	dichloromethane	N Param.: -1.18 s_N Param.: 1.20	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
arginine (betaine, in water)	water	N Param.: 12.96 s_N Param.: 0.57	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
asparagine (anionic, in water)	water	N Param.: 13.03 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
aspartate (dianionic, in water)	water	N Param.: 13.81 s_N Param.: 0.53	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
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
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
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
azide ion (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.54 s_N Param.: 0.82	J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063
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
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
azulene	MeCN	N Param.: 6.66 s_N Param.: 1.02	Eur. J. Org. Chem. 2009, , 1202-1206 10.1002/ejoc.200801099
barbiturate anion (in DMSO)	DMSO	N Param.: 15.59 s_N Param.: 0.80	J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223
benzimidazole (in DMSO)	DMSO	N Param.: 10.50 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
benzimidazole anion (in DMSO)	DMSO	N Param.: 19.13 s_N Param.: 0.55	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzoate (in 90AN10W)	aq MeCN	N Param.: 11.30 s_N Param.: 0.72	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
benzoate (in MeCN)	MeCN	N Param.: 16.82 s_N Param.: 0.70	J. Am. Chem. Soc. 2008, 130, 3012-3022 10.1021/ja0765464
benzoate (inMeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.72	J. Am. Chem. Soc. 2020, 142, 5221-5233 10.1021/jacs.9b12998
benzohydrazide (in MeCN)	MeCN	N Param.: 12.49 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
benzotriazole (in MeCN)	MeCN	N Param.: 7.69 s_N Param.: 0.76	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
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
benzotriazole anion (in water)	water	N Param.: 11.52 s_N Param.: 0.67	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
benzyl (1-phenylvinyl)carbamate	MeCN	N Param.: 6.21 s_N Param.: 0.87	Chem. Eur. J. 2012, 18, 5732-5740 10.1002/chem.201103519
benzyl isocyanide	dichloromethane	N Param.: 4.90 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2007, 46, 3563-3566 10.1002/anie.200605205
benzylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.46 s_N Param.: 0.62	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
benzylamine (in DMSO)	DMSO	N Param.: 15.28 s_N Param.: 0.65	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
benzylamine (in MeCN)	MeCN	N Param.: 14.29 s_N Param.: 0.67	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
benzylamine (in water)	water	N Param.: 13.44 s_N Param.: 0.55	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
benzyldimethylsilane	dichloromethane	N Param.: 2.78 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
beta-(trimethylsilyl)styrene	dichloromethane	N Param.: -0.43 s_N Param.: 1.06	Chem. Eur. J. 2014, 20, 1103-1110 10.1002/chem.201303215
beta-alanine (anionic, in water)	water	N Param.: 13.26 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
beta-piperidinium-peroxypropionate	water	N Param.: 13.94 s_N Param.: 0.62	Eur. J. Org. Chem. 2018, , 6010-6017 10.1002/ejoc.201801158
bis(4-(dimethylamino)phenyl)phenylmethane (in MeCN)	MeCN	N Param.: -4.20 s_N Param.: 0.82	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
bis(4-methoxyphenyl)phenylmethane (in MeCN)	MeCN	N Param.: -7.00 s_N Param.: 0.82	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bis(4-nitrophenyl)methanide (in DMSO)	DMSO	N Param.: 19.92 s_N Param.: 0.67	ARKIVOC 2008, (x), 37-53 10.3998/ark.5550190.[...]
bis(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 15.68 s_N Param.: 0.74	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
borane-2,6-lutidine-complex	dichloromethane	N Param.: 10.33 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-methoxypyridine-complex	dichloromethane	N Param.: 11.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-4-tBu-pyridine-complex	dichloromethane	N Param.: 10.46 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-DMAP-complex	dichloromethane	N Param.: 12.44 s_N Param.: 0.76	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diethylaniline-complex	dichloromethane	N Param.: 8.53 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N,N-diisopropylaniline-complex	dichloromethane	N Param.: 8.84 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-N-ethyl-N-isopropylaniline-complex	dichloromethane	N Param.: 9.12 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-pyridine-complex	dichloromethane	N Param.: 10.01 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
borane-triethylamine-complex	dichloromethane	N Param.: 8.90 s_N Param.: 0.75	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
borane-trimethylamine-complex	dichloromethane	N Param.: 7.97 s_N Param.: 0.75	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
bromide (in 20% aq MeCN)	water-MeCN mix	N Param.: 12.20 s_N Param.: 0.60	J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n
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
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