Nucleophiles

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Name	Solvent	Reactivity Parameters	Reference (title or year)
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
glycylglycylglycine (anionic, in water)	water	N Param.: 12.26 s_N Param.: 0.63	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycylglycine (anionic, in water)	water	N Param.: 12.91 s_N Param.: 0.59	Org. Biomol. Chem. 2007, 5, 3814-3820 10.1039/b713778h
glycinenitrile (in water)	water	N Param.: 10.80 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycineamide (in water)	water	N Param.: 12.29 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
glycine (anionic, in water)	water	N Param.: 13.51 s_N Param.: 0.58	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
glutamine (anionic, in water)	water	N Param.: 13.45 s_N Param.: 0.54	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
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
furan	dichloromethane	N Param.: 1.33 s_N Param.: 1.29	J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b
formohydrazide (in MeCN)	MeCN	N Param.: 10.35 s_N Param.: 0.76	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
fluorobis(phenylsulfonyl)methanide (in DMSO)	DMSO	N Param.: 17.46 s_N Param.: 0.73	Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616
fluoride (in water)	water	N Param.: 7.70 s_N Param.: 0.66	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in MeOH)	MeOH	N Param.: 11.31 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 98% aq MeCN)	water-MeCN mix	N Param.: 10.88 s_N Param.: 0.83	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 90% aq MeCN)	water-MeCN mix	N Param.: 12.27 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 80% aq MeCN)	water-MeCN mix	N Param.: 11.40 s_N Param.: 0.59	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 80% aq EtOH)	water-EtOH mix	N Param.: 13.20 s_N Param.: 0.53	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 60% aq MeCN)	water-MeCN mix	N Param.: 9.75 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
fluoride (in 10 % aq MeCN)	water-MeCN mix	N Param.: 8.05 s_N Param.: 0.64	J. Org. Chem. 2012, 77, 3325-3335 10.1021/jo300141z
ethylenediamine (in water)	water	N Param.: 13.28 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethyldimethylsilane	dichloromethane	N Param.: 3.30 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
ethylamine (in water)	water	N Param.: 12.87 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethyl-vinylether	dichloromethane	N Param.: 3.92 s_N Param.: 0.90	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
ethyl N-acetylcarbamate anion (in DMSO)	DMSO	N Param.: 15.99 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
ethyl glycinate (in DMSO)	DMSO	N Param.: 14.30 s_N Param.: 0.67	J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y
ethyl diazoacetate	dichloromethane	N Param.: 4.91 s_N Param.: 0.95	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
ethyl (E)-3-(N-morpholino)acrylate	dichloromethane	N Param.: 8.52 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethyl (E)-3-(dimethylamino)acrylate	dichloromethane	N Param.: 9.43 s_N Param.: 0.80	Chem. Eur. J. 2003, 9, 2209-2218 10.1002/chem.200204666
ethanolate (in ethanol)	EtOH	N Param.: 15.78 s_N Param.: 0.65	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolate (in 91E9AN)	EtOH-MeCN mix	N Param.: 16.08 s_N Param.: 0.62	Can. J. Chem. 2005, 83, 1554-1560 10.1139%2Fv05-170
ethanolamine (in water)	water	N Param.: 12.61 s_N Param.: 0.58	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
ethanolamine (in MeCN)	MeCN	N Param.: 14.11 s_N Param.: 0.71	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
ethanolamine (in DMSO)	DMSO	N Param.: 16.07 s_N Param.: 0.61	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
ethanolamine (in 91M9AN)	MeOH-MeCN mix	N Param.: 13.23 s_N Param.: 0.65	Angew. Chem. Int. Ed. 2006, 45, 3869-3874 10.1002/anie.200600542
ethanol (in MeCN)	MeCN	N Param.: 7.13 s_N Param.: 0.71	Bull. Chem. Soc. Jpn. 2018, 91, 523-530 10.1246/bcsj.20170360
ethanol	EtOH	N Param.: 7.44 s_N Param.: 0.90	J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z
enolate of 3-isochromanone (in DMSO)	DMSO	N Param.: 25.39 s_N Param.: 0.54	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
enolate of 2-coumaranone (in DMSO)	DMSO	N Param.: 19.60 s_N Param.: 0.75	J. Org. Chem. 2024, 89, 6915-6928 10.1021/acs.joc.4c00277
DMSO (O attack)	DMSO	N Param.: 11.30 s_N Param.: 0.74	J. Am. Chem. Soc. 2009, 131, 11392-11401 10.1021/ja903207b
ditert-butyl-phenylphosphane	dichloromethane	N Param.: 12.40 s_N Param.: 0.55	Chem. Eur. J. 2017, 23, 7422-7427 10.1002/chem.201701080
dipropylamine (in MeCN)	MeCN	N Param.: 14.51 s_N Param.: 0.80	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
dipp Imd boronate	dichloromethane	N Param.: 9.55 s_N Param.: 0.81	Org. Lett. 2012, 14, 82-85 10.1021/ol202836p
diphenylsilane	dichloromethane	N Param.: 1.52 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diphenyldiazomethane	dichloromethane	N Param.: 5.29 s_N Param.: 0.92	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
dimethylsulfide (in MeCN)	MeCN	N Param.: 12.70 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
dimethylsulfide (in CH2Cl2)	dichloromethane	N Param.: 12.32 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
dimethylselenide (in CH2Cl2)	dichloromethane	N Param.: 12.60 s_N Param.: 0.72	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
dimethylamine (in water)	water	N Param.: 17.12 s_N Param.: 0.50	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
dimethylamine (in MeCN)	MeCN	N Param.: 17.96 s_N Param.: 0.63	J. Org. Chem. 2012, 77, 8142-8155 10.1021/jo301497g
dimethyl(propoxy)silane	dichloromethane	N Param.: 2.40 s_N Param.: 0.75	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(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(neopentyl)silane	dichloromethane	N Param.: 3.55 s_N Param.: 0.73	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((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 diazomalonate	dichloromethane	N Param.: -1.24 s_N Param.: 0.81	J. Am. Chem. Soc. 2023, 145, 7416-7434 10.1021/jacs.2c13872
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 1,1'-isopropylidenezirconocene	dichloromethane	N Param.: 5.20 s_N Param.: 1.00	Chem. Eur. J. 2016, 22, 11196-11200 10.1002/chem.201602452
dimethoxymethane	dichloromethane	N Param.: -4.90 s_N Param.: 0.80	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
dihexylsilane	dichloromethane	N Param.: 2.27 s_N Param.: 0.73	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
diethylether (in dichloromethane)	dichloromethane	N Param.: -5.10 s_N Param.: 0.80	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethylamine (in water)	water	N Param.: 14.68 s_N Param.: 0.53	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
diethylamine (in MeCN)	MeCN	N Param.: 15.10 s_N Param.: 0.73	Eur. J. Org. Chem. 2009, , 6379-6385 10.1002/ejoc.200900925
diethyl(methyl)silane	dichloromethane	N Param.: 3.40 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
diethyl diazomalonate	dichloromethane	N Param.: -0.35 s_N Param.: 0.93	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diethanolamine (in water)	water	N Param.: 13.00 s_N Param.: 0.61	J. Org. Chem. 2007, 72, 3679-3688 10.1021/jo062586z
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 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
dichloro(methyl)silane	dichloromethane	N Param.: -3.20 s_N Param.: 0.73	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
dibutylsulfide (in CH2Cl2)	dichloromethane	N Param.: 11.86 s_N Param.: 0.74	Chem. Eur. J. 2021, 21, 11367-11376 10.1002/chem.202100977
diazomethane	dichloromethane	N Param.: 10.48 s_N Param.: 0.78	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
diazoacetone	dichloromethane	N Param.: 3.96 s_N Param.: 0.91	Chem. Eur. J. 2003, 9, 4068-4076 10.1002/chem.200304913
diacetamide anion (in DMSO)	DMSO	N Param.: 16.05 s_N Param.: 0.70	J. Org. Chem. 2010, 75, 5250-5258 10.1021/jo1009883
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
DHPB (3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine)	dichloromethane	N Param.: 13.86 s_N Param.: 0.78	J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x
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
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
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 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 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 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
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
DBU (in MeCN)	MeCN	N Param.: 15.29 s_N Param.: 0.70	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
DBN (in MeCN)	MeCN	N Param.: 16.28 s_N Param.: 0.67	Chem. Commun. 2008, , 1792-1794 10.1039/b801811a
DBN (in CH2Cl2)	dichloromethane	N Param.: 15.50 s_N Param.: 0.76	ChemCatChem 2012, 4, 993-999 10.1002/cctc.201200143
Danishefskys diene	dichloromethane	N Param.: 8.57 s_N Param.: 0.84	J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y
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
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
cyclopentene	dichloromethane	N Param.: -1.55 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
cycloocta-1,3-diene	dichloromethane	N Param.: -0.50 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cyclohexa-1,3-diene	dichloromethane	N Param.: 0.67 s_N Param.: 1.10	Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c
cycloheptatriene (in MeCN)	MeCN	N Param.: 0.55 s_N Param.: 0.97	Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839
cycloheptatriene	dichloromethane	N Param.: 0.52 s_N Param.: 0.97	J. Am. Chem. Soc. 2002, 124, 4076-4083 10.1021/ja0121538