Loading...
Please wait, while we are loading the content...
Similar Documents
Nucleophilic Radiofluorination Using Tri-tert-Butanol Ammonium as a Bifunctional Organocatalyst: Mechanism and Energetics
| Content Provider | MDPI |
|---|---|
| Author | Oh, Young-Ho Shinde, Sandip S. Lee, Sungyul |
| Copyright Year | 2022 |
| Description | We present a quantum chemical analysis of the$ ^{18}$F-fluorination of 1,3-ditosylpropane, promoted by a quaternary ammonium salt (tri-(tert-butanol)-methylammonium iodide (TBMA-I) with moderate to good radiochemical yields (RCYs), experimentally observed by Shinde et al. We obtained the mechanism of the $S_{N}$2 process, focusing on the role of the –OH functional groups facilitating the reactions. We found that the counter-cation $TBMA^{+}$ acts as a bifunctional promoter: the –OH groups function as a bidentate ‘anchor’ bridging the nucleophile $[^{18}F]F^{−}$ and the –OTs leaving group or the third –OH. These electrostatic interactions cooperate for the formation of the transition states of a very compact configuration for facile $S_{N}$2$ ^{18}$F-fluorination. |
| Starting Page | 1044 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules27031044 |
| Journal | Molecules |
| Issue Number | 3 |
| Volume Number | 27 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2022-02-03 |
| Access Restriction | Open |
| Subject Keyword | Molecules 18f-fluorination Tri-tert-butanol Ammonium Organocatalysis Mechanism |
| Content Type | Text |
| Resource Type | Article |
