Search
| Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
|---|---|---|---|---|
3,5-bis(trifluoromethyl)thiophenolate (in DMSO)  |
DMSO | N Param.: 19.71 sN Param.: 0.86 |  | J. Org. Chem. 2021, 86, 5965-5972 10.1021/acs.joc.1c00025 |
3,5,6,7-tetrahydro-2H-imidazo[2,1-b][1,3]thiazine |
dichloromethane | N Param.: 13.00 sN Param.: 0.83 | | J. Org. Chem. 2011, 76, 5104-5112 10.1021/jo200803x |
3,3-dimethyl-2-(trimethylsiloxy)buten |
dichloromethane | N Param.: 3.78 sN Param.: 0.79 | | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y |
3,3,3-trifluoro-2-(trimethylsiloxy)propene |
dichloromethane | N Param.: -2.94 sN Param.: 1.11 | | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w |
3% water/97% HFIP (w/w) |
water-HFIP mix | N Param.: -1.19 sN Param.: 1.08 | | J. Phys. Org. Chem. 2013, 26, 59-63 10.1002/poc.3064 |
2H-benzo[d][1,3]dithiol-2-ide 1,1,3,3-tetraoxide (in DMSO) |
DMSO | N Param.: 16.06 sN Param.: 0.69 | | Angew. Chem. Int. Ed. 2016, 55, 12845-12848 10.1002/anie.201605616 |
20% water/80%TFE (v/v) |
water-TFE mix | N Param.: 3.20 sN Param.: 0.88 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
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 |
20% water/80% MeCN (v/v) |
water-MeCN mix | N Param.: 5.02 sN Param.: 0.89 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% water/80% acetone (v/v) |
water-acetone mix | N Param.: 5.77 sN Param.: 0.87 | | Angew. Chem. Int. Ed. 2004, 43, 2302-2305 10.1002/anie.200353468 |
20% methanol/80% MeCN (v/v) |
MeOH-MeCN mix | N Param.: 6.04 sN Param.: 0.94 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
20% ethanol/80% MeCN (v/v) |
EtOH-MeCN mix | N Param.: 5.77 sN Param.: 0.92 | | J. Am. Chem. Soc. 2004, 126, 5174-5181 10.1021/ja031828z |
2-tritylpyrrolidine |
MeCN | N Param.: 9.16 sN Param.: 1.39 | | J. Am. Chem. Soc. 2020, 142, 1526-1547 10.1021/jacs.9b11877 |
2-thiobarbiturate anion (in DMSO) |
DMSO | N Param.: 14.24 sN Param.: 0.82 | | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 |
2-sulfidoacetate (in water) |
water | N Param.: 22.62 sN Param.: 0.43 | | J. Am. Chem. Soc. 2003, 125, 286-295 10.1021/ja021010y |
2-pyridone anion (in water) |
water | N Param.: 12.47 sN Param.: 0.52 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in MeCN) |
MeCN | N Param.: 20.11 sN Param.: 0.57 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-pyridone anion (in DMSO) |
DMSO | N Param.: 19.91 sN Param.: 0.60 | | J. Am. Chem. Soc. 2010, 132, 15380-15389 10.1021/ja106962u |
2-propyl-1,3-dioxolane |
dichloromethane | N Param.: -1.06 sN Param.: 0.81 | | Chem. Eur. J. 2013, 19, 249-263 10.1002/chem.201202839 |
2-phenylperoxyacetate (in H2O) |
water | N Param.: 15.63 sN Param.: 0.56 | | Angew. Chem. Int. Ed. 2017, 56, 13279-13282 10.1002/anie.201707086 |
News
- 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).