Mechanism of the Swern oxidation: Associated transition states for K1-k4 vs K0 vs Kinv (Scheme 1)
DOI: 10.14469/hpc/13106 Metadata
Created: 2023-08-22 09:44
Last modified: 2023-10-18 18:26
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
Gaussian 16 calculations for the initial proton transfer to generate the SWERN reagent and the TS for inversion of configuration at Sulfur
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| Scheme4.svg | 53KB | image/svg+xml | Scheme showing rate constant labelling |
| Scheme4.cdxml | 30KB | chemical/x-cdxml | Scheme4 as CDXML |
Member of collection / collaboration
| DOI | Description |
|---|---|
| 10.14469/hpc/13058 | Modelling kinetic isotope effects for SWERN Oxidation. DFT-based transition structure Theory is OK. |
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/13086 | Swern, initial proton abstraction by NMe3 in the presence of Cl(-), TS, Def2-TZVPP, G = -1458.941651 DG = +7.1 kcal/mol, IRC |
| 10.14469/hpc/13087 | Swern, initial reactant prior to proton abstraction by NMe3 in the presence of Cl(-) (next to NMe3), Def2-TZVPP,G = -1458.953205 |
| 10.14469/hpc/13085 | Swern, initial reactant prior to proton abstraction by NMe3 in the presence of Cl(-) (next to S), Def2-TZVPP, G = -1458.965242 |
| 10.14469/hpc/13068 | Swern, TS for exo S-inversion, Def2-QZVPP, superfine, G = -823.604044, ΔG = 30.2 (G = -823.652146 for pericyclic TS) ==> IRC |
| 10.14469/hpc/13090 | Cl(-)NHMe3(+), Def2-TZVPP, iso position for Cl(-) G -635.345558 = (+ TS1 endo = -823.61242) == -1,458.957978 (Supermolecule TS -1458.953030) |
| 10.14469/hpc/13353 | PT mechanism for inversion/endo-exo isomerisation via proton transfer to trimethylamine, B3LYP+GD+BJ/Def2-TZVPP/IEFPCM. G = -1458.946171 |
| 10.14469/hpc/12404 | Swern, TS for exo S-inversion, Def2-QZVPP/CPCM, superfine, G = -823.604044, ΔG= 30.2 kcal/mol (G = -823.652146 for pericyclic H-transfer TS) |
| 10.14469/hpc/13359 | Cl(-)NHMe3(+), Def2-QZVPP, iso position for Cl(-), G = -635.375344 |
| 10.14469/hpc/13358 | Exo_TS1_G16_CPCM_dichloromethane_def2qzvpp_reactant, + dispersion correction, G= -823.663469 |
| 10.14469/hpc/13360 | Swern, TS for exo S-inversion, CPCM, Def2-TZVPP, superfine, G = -823.564166 |
| 10.14469/hpc/13084 | Swern, initial TS for proton abstraction by NMe3 + Cl(-), Def2-TZVPP/CPCM (G = -1458.953030/-1,458.957978, for pericyclic TS, reactant = -1458.965242) G = -1458.941651 DG = 14.8, DDG = +7.1/10.2 kcal/mol |
| 10.14469/hpc/12391 | Swern oxidation, TS1 exo, B3LYP+GD3+BJ/Def2-QZVPP, superfine, SCRF=CPCM/DCM, G = -823.652169 |
| 10.14469/hpc/13366 | Exo_TS1_G16_CPCM_dichloromethane_def2tzvpp + dispersion correction, G =-823.612827 |
| 10.14469/hpc/12396 | Swern, TS in the presence of Cl(-)NHMe3(+), Def2-TZVPP, G = -1458.953030 |
| 10.14469/hpc/12372 | Swern oxidation, TS1 endo, B3LYP+GD3+BJ/Def2-TZVPP, SCRF=CPCM, G = -823.61242 mu -398.1 |
| 10.14469/hpc/13367 | Swern, initial TS for proton abstraction by NMe3 + Cl(-), Def2-QZVPP/CPCM, G = -1459.011059 |
| 10.14469/hpc/13368 | Swern, initial reactant prior to proton abstraction by NMe3 in the presence of Cl(-) (next to S), Def2-QZVPP, G = -1459.034212 |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.14469/hpc/13107 | Mechanism of the Swern oxidation: Models including Me3N/Me3NH/Cl(-) |
Subject Keywords
| Keyword | Value |
|---|---|
| inchi | InChI=1S/C11H17OS/c1-10(2)13(3)12-9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3/q+1/i9D/t9-,13?/m0/s1 |
| inchikey | KOTGBTPJOGQKJE-RRDWHHOZSA-N |