Rappe Rearrangement. The origin of cis-stereoselectivity in the conversion of 2,3-dibromo-2-methyl-cyclopropan-1-one to (Z)-but-2-enoic acid. Products and Thermochemistry of overall reaction
DOI: 10.14469/hpc/15063 Metadata
Created: 2025-03-24 13:11
Last modified: 2025-05-14 09:11
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
Gaussian16 calculation
Member of collection / collaboration
| DOI | Description |
|---|---|
| 10.14469/hpc/11172 | The Mechanism of the Rappe Rearrangement – a stereochemical investigation using Density Functional Theory. |
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/15069 | Rappe, Product 3, G = -5379.196842 |
| 10.14469/hpc/15071 | Rappe product 5, trans alkenoic acid, G = -306.457027 |
| 10.14469/hpc/15068 | Rappe Rearrangement. Water, ωB97XD/Def2-TZVPP G = -76.444400 |
| 10.14469/hpc/15078 | Rappe Rearrangement. HBr, wB97XD/Def2-TZVPP G = -2574.836655 |
| 10.14469/hpc/15079 | Rappe rearrangement, 7, wB97XD/Def2-TZVPP, cis G = -2881.232889 |
| 10.14469/hpc/15066 | Rappe Rearrangement. Br(-) ωB97XD/Def2-TZVPP G = -2574.417150 |
| 10.14469/hpc/15072 | Rappe Rearrangement, product 5, cis alkenoic acid, G = -306.453670, ΔG = 2.1 kcal/mol |
| 10.14469/hpc/15067 | Rappe Rearrangement. Hydroxide anion, ωB97XD/Def2-TZVPP G = -75.928002 |
| 10.14469/hpc/15070 | Rappe Rearrangement. Reactant 1. ωB97XD/Def2-TZVPP, G = -5379.662078 |
Associated DOIs
| Current dataset ... | DOI | Description |
|---|---|---|
| References | 10.14469/hpc/10996 | Rappe Rearrangement. TS1a. G = -5379.163716 |
| References | 10.14469/hpc/11037 | Rappe Rearrangement. 2, G = -5379.184488 |
| References | 10.14469/hpc/11046 | Rappe Rearrangement. 7, G = -2881.232889 |
| References | 10.14469/hpc/11053 | Rappe Rearrangement. TS2 (cis), G = -2880.744525 |
| References | 10.14469/hpc/11175 | Rappe Rearrangement. 4, G = -2880.751741 |
| References | 10.14469/hpc/11223 | Rappe Rearrangement. TS8, G = -2804.748221 |