Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
gamma-aminobutyric acid (anionic, in water)	water	N Param.: 13.55 s_N Param.: 0.56	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutamate (dianionic, in water)	water	N Param.: 13.96 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glutathione GSH(NH3+/S-)	water	N Param.: 20.97 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2019, 58, 17704-17708 10.1002/anie.201909803
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycineamide (in water)	water	N Param.: 12.29 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycinenitrile (in water)	water	N Param.: 10.80 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycylglycine (anionic, in water)	water	N Param.: 12.91 s_N Param.: 0.59	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycylglycylglycine (anionic, in water)	water	N Param.: 12.26 s_N Param.: 0.63	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
guanine anion (in water)	water	N Param.: 11.63 s_N Param.: 0.59	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
guanosine anion (in water)	water	N Param.: 12.09 s_N Param.: 0.52	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
H2O (in water)	water	N Param.: 5.20 s_N Param.: 0.89	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
Hantzsch ester	dichloromethane	N Param.: 9.00 s_N Param.: 0.90	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
HCr(CO)3Cp*	dichloromethane	N Param.: 1.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
hexylsilane	dichloromethane	N Param.: 0.19 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HFe(CO)2Cp*	dichloromethane	N Param.: 8.20 s_N Param.: 0.69	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
histidine (anionic, in water)	water	N Param.: 13.83 s_N Param.: 0.54	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
HMn(CO)5	dichloromethane	N Param.: 1.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HMo(CO)3Cp*	dichloromethane	N Param.: 4.30 s_N Param.: 0.77	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HMo(Cp)(CO)3	dichloromethane	N Param.: 4.88 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HOO- (in water)	water	N Param.: 15.40 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
HOs(CO)2Cp*	dichloromethane	N Param.: 5.20 s_N Param.: 0.95	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HRe(CO)5	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HRu(CO)2Cp*	dichloromethane	N Param.: 8.00 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
HW(CO)3(C5H4Me)	dichloromethane	N Param.: 2.40 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3(indenyl)	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3Cp	dichloromethane	N Param.: 1.70 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(CO)3Cp*	dichloromethane	N Param.: 3.50 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
HW(NO)2Cp	dichloromethane	N Param.: 4.70 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
hydantoin anion (in DMSO)	DMSO	N Param.: 17.52 s_N Param.: 0.55	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
hydrazine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.47 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
hydrazine (in MeCN)	MeCN	N Param.: 16.45 s_N Param.: 0.56	Angew. Chem. Int. Ed. 2012, 51, 1353-1356 10.1002/anie.201107315
hydrazine (in water)	water	N Param.: 13.46 s_N Param.: 0.57	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 12.23 s_N Param.: 0.66	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
hydroxylamine (in MeCN)	MeCN	N Param.: 12.80 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
hydroxylamine (in water)	water	N Param.: 11.41 s_N Param.: 0.55	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
hypobromite (in water)	water	N Param.: 16.69 s_N Param.: 0.46	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
hypochlorite (in water)	water	N Param.: 14.50 s_N Param.: 0.58	Org. Lett. 2018, 20, 2816-2820 10.1021/acs.orglett.[...]
imidazole (in 91M9AN)	MeOH-MeCN mix	N Param.: 10.41 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
imidazole (in DMSO)	DMSO	N Param.: 11.58 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole (in MeCN)	MeCN	N Param.: 11.47 s_N Param.: 0.79	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole (in water)	water	N Param.: 9.63 s_N Param.: 0.57	Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b
imidazole anion (in DMSO)	DMSO	N Param.: 21.09 s_N Param.: 0.51	Chem. Eur. J. 2012, 18, 127-137 10.1002/chem.201102411
Indole	dichloromethane	N Param.: 5.55 s_N Param.: 1.09	J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339
isobutylenyl-ethylether	dichloromethane	N Param.: 4.23 s_N Param.: 1.00	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
isopropanol (in aq. sulfuric acid)	water	N Param.: -2.60 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
isopropanol (in MeCN)	MeCN	N Param.: 6.82 s_N Param.: 0.70	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
isopropanolate (in 91iPr9AN)	iPrOH-MeCN mix	N Param.: 17.71 s_N Param.: 0.58	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropanolate (in propan-2-ol)	iPrOH	N Param.: 17.03 s_N Param.: 0.63	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
isopropylamine (in MeCN)	MeCN	N Param.: 13.77 s_N Param.: 0.70	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
isopropylamine (in water)	water	N Param.: 12.00 s_N Param.: 0.56	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
KBH4 (in DMSO)	DMSO	N Param.: 15.14 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263
leucine (anionic, in water)	water	N Param.: 14.01 s_N Param.: 0.52	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
lithium (5-methylfuran-2-yl)(4-(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 8.13 s_N Param.: 0.85	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)glycolborate	MeCN	N Param.: 11.23 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 10.13 s_N Param.: 0.91	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(3,5-bis(trifluoromethyl)phenyl)pinacolborate	MeCN	N Param.: 5.53 s_N Param.: 1.00	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(dimethylamino)phenyl)pinacolborate	MeCN	N Param.: 8.02 s_N Param.: 0.89	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)catecholglycolborate	MeCN	N Param.: 6.50 s_N Param.: 0.77	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-(trifluoromethyl)phenyl)neopentylglycolborate	MeCN	N Param.: 11.85 s_N Param.: 0.72	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-chlorophenyl)pinacolborate	MeCN	N Param.: 6.77 s_N Param.: 0.88	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methoxyphenyl)pinacolborate	MeCN	N Param.: 7.51 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(4-methylphenyl)pinacolborate	MeCN	N Param.: 6.98 s_N Param.: 0.93	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (5-methylthiophen-2-yl)(phenyl)pinacolborate	MeCN	N Param.: 7.24 s_N Param.: 0.83	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium (E)-2-(3,5-bis(trifluoromethyl)phenyl)-2-(but-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 9.49 s_N Param.: 0.82	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.46 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-allyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.71 s_N Param.: 0.80	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium 2-allyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.20 s_N Param.: 0.64	J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.30 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.15 s_N Param.: 0.77	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.92 s_N Param.: 0.70	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.72 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 7.68 s_N Param.: 0.78	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 6.63 s_N Param.: 0.75	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 8.56 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 10.97 s_N Param.: 0.63	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolan-2-uide (in MeCN)	MeCN	N Param.: 11.00 s_N Param.: 0.57	J. Am. Chem. Soc. 2022, 144, 16118-16130 10.1021/jacs.2c06493
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN)	MeCN	N Param.: 11.29 s_N Param.: 0.76	Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...]
lithium bis(5-methylthiophen-2-yl)pinacolborate	MeCN	N Param.: 7.67 s_N Param.: 0.87	Angew. Chem. Int. Ed. 2015, 54, 2780-2783 10.1002/anie.201410562
lithium indenide (in DMSO)	DMSO	N Param.: 23.66 s_N Param.: 0.70	Angew. Chem. Int. Ed. 2015, 54, 12497-12500 10.1002/anie.201501385
m-(trifluoromethyl)phenolate (in DMF)	DMF	N Param.: 23.40 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in DMSO)	DMSO	N Param.: 22.62 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-(trifluoromethyl)phenolate (in MeCN)	MeCN	N Param.: 23.20 s_N Param.: 0.51	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-methoxyphenolate (in MeCN)	MeCN	N Param.: 18.81 s_N Param.: 0.80	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMF)	DMF	N Param.: 22.41 s_N Param.: 0.54	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.54	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-nitrophenolate (in MeCN)	MeCN	N Param.: 25.51 s_N Param.: 0.43	J. Org. Chem. 2019, 84, 8837-8858 10.1021/acs.joc.9b01485
m-xylene	dichloromethane	N Param.: -3.57 s_N Param.: 2.08	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
magnesium 2-carboperoxybenzoate (in H2O)	water	N Param.: 18.43 s_N Param.: 0.46	Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086
maleimide anion (in DMSO)	DMSO	N Param.: 14.87 s_N Param.: 0.76	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
Me2 Imd boronate	dichloromethane	N Param.: 11.88 s_N Param.: 0.71	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
Me2S(O)=CH2 (in DMSO)	DMSO	N Param.: 21.29 s_N Param.: 0.47	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S=CH(4-CN-C6H4) (in DMSO)	DMSO	N Param.: 21.07 s_N Param.: 0.68	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S=CH(p-NO2-C6H4) (in DMSO)	DMSO	N Param.: 18.42 s_N Param.: 0.65	J. Am. Chem. Soc. 2010, 132, 17894-17900 10.1021/ja1084749
Me2S=CH-CN (in DMSO)	DMSO	N Param.: 16.23 s_N Param.: 0.60	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
Me2S=CH-CO2Et (in DMSO)	DMSO	N Param.: 15.85 s_N Param.: 0.61	Chem. Eur. J. 2010, 16, 8610-8614 10.1002/chem.201001455
Meldrum's acid iodonium ylide (in CH2Cl2)	dichloromethane	N Param.: 4.36 s_N Param.: 1.06	J. Am. Chem. Soc. 2016, 138, 10304-10313 10.1021/jacs.6b05768
MeO-Breslow 1a	THF	N Param.: 14.77 s_N Param.: 0.80	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524
MeO-Breslow 1b	THF	N Param.: 10.45 s_N Param.: 0.81	Angew. Chem. Int. Ed. 2012, 51, 10408-10412 10.1002/anie.201204524