Search
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
chloride (in CF3CH2OH)  |
TFE | N Param.: 10.30 sN Param.: 0.60 |  | J. Am. Chem. Soc. 2005, 127, 2641-2649 10.1021/ja045562n |
azide ion (in 91M9AN) |
MeOH-MeCN mix | N Param.: 14.54 sN Param.: 0.82 | | J. Phys. Org. Chem. 2006, 19, 706-713 10.1002/poc.1063 |
4-chloropyridine (in CH2Cl2) |
dichloromethane | N Param.: 11.70 sN Param.: 0.67 | | Chem. Eur. J. 2007, 13, 336-345 10.1002/chem.200600941 |
Ph3P=CH-CN |
dichloromethane | N Param.: 12.29 sN Param.: 0.75 | | J. Am. Chem. Soc. 2009, 131, 704-714 10.1021/ja8056216 |
2,5-dimethyl-benzimidazole (in DMSO) |
DMSO | N Param.: 10.21 sN Param.: 0.85 | | Org. Biomol. Chem. 2010, 8, 1929-1935 10.1039/c000965b |
5-(trimethylsiloxy)-2,3-dihydrofuran (in MeCN) |
MeCN | N Param.: 12.34 sN Param.: 0.72 | | J. Am. Chem. Soc. 2013, 135, 6579-6587 10.1021/ja401106x |
p-chloranil (C=O) |
E Param.: -12.13 | | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | |
(E)-1-methyl-4-(styrylsulfonyl)benzene (in DMSO) |
DMSO | E Param.: -24.69 | | J. Am. Chem. Soc. 2017, 139, 13318-13329 10.1021/jacs.7b05106 |
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 sN Param.: 0.80 | | J. Am. Chem. Soc. 2017, 139, 15324-15327 10.1021/jacs.7b10240 |
50% ethanol/50% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 6.37 sN Param.: 0.90 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
N-(p-anisyl)-1,4-dihydronicotineamide |
dichloromethane | N Param.: 8.11 sN Param.: 0.92 | | Angew. Chem. Int. Ed. 2009, 48, 1958-1961 10.1002/anie.200804263 |
(4-Me)2-tritylium ion |
E Param.: -0.70 |  | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y | |
(Z)-1-(1,3-dimesityl-4,5-dihydro-1H-imidazol-3-ium-2-yl)-2-phenylprop-1-en-1-olate (in THF) |
THF | N Param.: 15.92 sN Param.: 0.72 | | Angew. Chem. Int. Ed. 2013, 52, 11163-11167 10.1002/ange.201303524 |
1-(isoquinolin-2-ium-2-yl)-2-oxo-2-phenylethan-1-ide (in DMSO) |
DMSO | N Param.: 20.08 sN Param.: 0.57 | | J. Am. Chem. Soc. 2013, 135, 15216-15224 10.1021/ja407885h |
p-quinone (C-H) |
E Param.: -16.19 | | J. Am. Chem. Soc. 2014, 136, 11499-11512 10.1021/ja505613b | |
methylenecyclobutane |
dichloromethane | N Param.: 1.65 sN Param.: 0.90 | | Acc. Chem. Res. 2003, 36, 66-77 10.1021/ar020094c |
(bis(trimethylsiloxy)amino)styrene |
dichloromethane | N Param.: 4.80 sN Param.: 0.86 | | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 |
cyclohepta-1,3,5-trienyl-Fe(CO)3 |
dichloromethane | N Param.: 3.42 sN Param.: 0.94 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
pop(Ph)CH+ |
E Param.: 2.90 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
20% water/80%EtOH (v/v) |
water-EtOH mix | N Param.: 6.68 sN Param.: 0.85 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
News
- 03/20/26:
NaOCP by Breugst and Lakhdar has been added to the P-nucleophiles (Chem. Sci. 2024, 15, 14406-14414). - 03/20/26:
Glycals (cyclic enol ethers) by Lakhdar, Robiette, Vincent, and Berionni have been added (Angew. Chem. Int. Ed. 2026, EarlyView, e243229). - 03/18/26:
Vinyl azides have been added (Chem. Commun. 2026, 62, 5041). - 02/23/26:
Isochalcogenoureas (O, S, Se & Te derivatives) have been added (ChemistryEurope 2026, 4, e202500443 & Angew. Chem. Int. Ed. 2025, 64, e202514865). - 01/30/25:
Sesamol-derived ortho-quinone methides (o-QM) have been added (ChemEurJ 2024, e202403785 & OBC 2025, 23, 827-834) - 05/22/24:
Lactone enolates have been added (JOC 2024, 89, 6915-6928). - 11/13/24:
2-Methylene-1,2-dihydropyridines (2-pyNHOs) have been added (EurJOC 2024, 27, e202400373). - 05/21/24:
Mesoionic pyridinium-derived N-heterocyclic olefins (py-mNHOs) have been added (Angew. Chem. Int. Ed. 2024, 63, e202318283). - 10/19/23:
Enamines derived from 4-(alkylthio)-3-imidazolines and aldehydes have been added (ChemEurJ 2023, doi: 10.1002/chem.202302764). - 09/28/23:
Mesoionic N-heterocyclic olefins (mNHOs) have been added (Angew. Chem. Int. Ed. 2023, 62, e202309790). - 07/05/23:
S-Cyanomethylated imidazolidine-4-thione-derived enamines have been added (ChemComm 2023, 59, 8091). - 03/16/23:
Cyclic alpha-diazo carbonyl compounds added (EurJOC 2023, 26, e202300005) - 01/30/23:
NADH and NADPH reactivities (in water, pH 7) determined by Mayer and Moran have been added (OBC 2022, 21, 85-88). - 09/20/22:
Alkenyl boronate nucleophilicity by Liu, Ready and co-workers has been added (JACS 2022, 144, 16118). - 01/30/23:
Electrophilicities of diazo compounds in azo couplings (ChemEurJ 2022, 28, e202201376) - 01/30/23:
Diazocyclopentadiene added (Synthesis 2023, 55, 354-358) - 01/30/23:
Electrophilic indoles added (ChemCommun 2021, 57, 10071-10074) - 04/13/21:
Cyclic Michael acceptors added (Chem. Sci. 2021, 12, 4850-4865) - 05/21/21:
Thiophenolates (in DMSO) added (JOC 2021, 86, 5965-5972) - 05/06/20:
Heteroallenes added (JACS 2020, 142, 8383-8402). - 01/27/20:
Pyrrolidines and Imidazolidinones added (JACS 2020, 142, 1526-1547). - 05/06/20:
GSH reactivity added (Angew. Chem. Int. Ed. 2019, 58, 17704-17708) - 01/30/23:
Phenolates added (JOC 2019, 84, 8837-8858) - 04/24/18:
Ketones added (JACS 2018, 140, 5500). - 11/03/17:
Allyl-boron nucleophiles added (JACS 2017, 139, 15324) - 04/23/18:
Peroxide anions added (Angew. Chem. Int. Ed. 2017, 56, 13279). - 04/23/18:
Michael acceptors added (JACS 2017, 139, 13318). - 06/16/17:
Nucleophilicities of VNS reagents (JOC 2017, 82, 1011).