Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
anion of 4-methylbenzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 19.35 s_N Param.: 0.67	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of 4-nitrobenzyl trifluoromethyl sulfone (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.66	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of 4-nitrobenzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 14.49 s_N Param.: 0.86	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of 4-nitrobenzyl-CN (in DMSO)	DMSO	N Param.: 19.67 s_N Param.: 0.68	J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x
anion of 4-nitrobenzyl-CN (in MeCN)	MeCN	N Param.: 20.10 s_N Param.: 0.71	J. Am. Chem. Soc. 2020, 142, 8383-8402 10.1021/jacs.0c01960
anion of 5-(p-anisyl) Meldrum's acid (in DMSO)	DMSO	N Param.: 12.35 s_N Param.: 0.90	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of 5-phenyl Meldrum's acid (in DMSO)	DMSO	N Param.: 11.54 s_N Param.: 0.95	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of acetylacetone (in DMSO)	DMSO	N Param.: 17.64 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of acetylacetone (in water)	water	N Param.: 13.73 s_N Param.: 0.64	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of benzyl trifluoromethyl sulfone (in DMSO)	DMSO	N Param.: 18.67 s_N Param.: 0.68	J. Am. Chem. Soc. 2007, 129, 9753-9761 10.1021/ja072135b
anion of diethyl 2-(4-nitrophenyl)malonate (in DMSO)	DMSO	N Param.: 14.94 s_N Param.: 0.96	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(acetyl)malonate (in DMSO)	DMSO	N Param.: 13.83 s_N Param.: 0.84	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(benzoyl)malonate (in DMSO)	DMSO	N Param.: 13.63 s_N Param.: 0.80	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(isopropyl)malonate (in DMSO)	DMSO	N Param.: 18.74 s_N Param.: 0.71	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-(p-anisyl)malonate (in DMSO)	DMSO	N Param.: 16.73 s_N Param.: 0.91	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-butylmalonate (in DMSO)	DMSO	N Param.: 23.00 s_N Param.: 0.55	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-cyclohexylmalonate (in DMSO)	DMSO	N Param.: 19.23 s_N Param.: 0.67	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl 2-phenylmalonate (in DMSO)	DMSO	N Param.: 15.93 s_N Param.: 0.99	Eur. J. Org. Chem. 2016, , 1841-1848 10.1002/ejoc.201600107
anion of diethyl malonate (in DMSO)	DMSO	N Param.: 20.22 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of diethyl malonate (in water)	water	N Param.: 16.15 s_N Param.: 0.66	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of diethyl methylmalonate (in DMSO)	DMSO	N Param.: 21.13 s_N Param.: 0.68	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of diethyl methylmalonate (in water)	water	N Param.: 17.68 s_N Param.: 0.50	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of dimedone (in DMSO)	DMSO	N Param.: 16.27 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of dimedone (in water)	water	N Param.: 11.77 s_N Param.: 0.63	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of dimethyl malonate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.24 s_N Param.: 0.64	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of ethyl 2-cyano-2-phenylacetate (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 1.04	Eur. J. Org. Chem. 2017, , 1196-1202 10.1002/ejoc.201601513
anion of ethyl 2-nitroacetate (in DMSO)	DMSO	N Param.: 15.24 s_N Param.: 0.74	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of ethyl 3-oxo-3-phenylpropanoate (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.74	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of ethyl acetylacetate (in DMSO)	DMSO	N Param.: 18.82 s_N Param.: 0.69	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of ethyl acetylacetate (in water)	water	N Param.: 15.99 s_N Param.: 0.62	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of ethyl cyanoacetate (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.59 s_N Param.: 0.65	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of ethyl cyanoacetate (in DMSO)	DMSO	N Param.: 19.62 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of ethyl cyanoacetate (in water)	water	N Param.: 15.57 s_N Param.: 0.58	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of malononitrile (in 91M9AN)	MeOH-MeCN mix	N Param.: 18.21 s_N Param.: 0.69	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of malononitrile (in DMSO)	DMSO	N Param.: 19.36 s_N Param.: 0.67	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of malononitrile (in water)	water	N Param.: 19.50 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of Meldrum's acid (in water)	water	N Param.: 12.06 s_N Param.: 0.66	J. Am. Chem. Soc. 2003, 125, 12980-12986 10.1021/ja036838e
anion of Meldrums acid (in DMSO)	DMSO	N Param.: 13.91 s_N Param.: 0.86	Angew. Chem. Int. Ed. 2002, 41, 91-95 10.1002/1521-3773(20[...]
anion of N,N-diethyl-3-oxo-3-phenylpropanoate (in DMSO)	DMSO	N Param.: 19.28 s_N Param.: 0.65	Chem. Eur. J. 2015, 21, 875-884 10.1002/chem.201404500
anion of nitroethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.41 s_N Param.: 0.67	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of nitroethane (in DMF)	DMF	N Param.: 22.21 s_N Param.: 0.48	Chem. Eur. J. 2008, 14, 6108-6118 10.1002/chem.200800329
anion of nitroethane (in DMSO)	DMSO	N Param.: 21.54 s_N Param.: 0.62	J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182
anion of nitroethane (in water)	water	N Param.: 11.25 s_N Param.: 0.52	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
anion of nitromethane (in 91M9AN)	MeOH-MeCN mix	N Param.: 14.02 s_N Param.: 0.61	Eur. J. Org. Chem. 2006, , 2530-2537 10.1002/ejoc.200500769
anion of nitromethane (in DMSO)	DMSO	N Param.: 20.71 s_N Param.: 0.60	J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j
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