Reactivity indices profile: a companion tool of the potential energy surface for the analysis of reaction mechanisms. Nucleophilic aromatic substitution reactions as test case
| dc.contributor.author | Ormazábal-Toledo, Rodrigo | |
| dc.contributor.author | Contreras, Renato | |
| dc.contributor.author | Campodónico, Paola | |
| dc.date.accessioned | 2017-04-10T13:03:44Z | |
| dc.date.available | 2017-04-10T13:03:44Z | |
| dc.date.issued | 2013 | |
| dc.description | Centro de Química Médica | |
| dc.description.abstract | We herein report on the usefulness of the reactivity indices profiles along a reaction coordinate. The model is tested to fully describe the reaction mechanism of the title reactions. Group nucleophilicity and electrophilicity profiles help describe the bond-breaking/bond-formation processes and the intramolecular electron density reorganization. The reactivity indices’ profile analysis is consistently complemented with hydrogen bonding (HB) effects along the reaction coordinate: the final outcome of the reaction is determined by the stage at which the HB complex can be formed. Transition-state structures located for six reactions studied, including the charged nucleophile thiocyanate, show that the main stabilizing interaction is that formed between the hydrogen atom of the nucleophile and the o-NO2 group. This result discards the role of HB interaction between the nucleophile and the leaving group previously proposed in the literature. | |
| dc.format.extent | 7 | |
| dc.identifier.citation | The Journal of Organic Chemistry, 2013, 78 (3):1091–1097 | |
| dc.identifier.uri | http://hdl.handle.net/11447/1119 | |
| dc.identifier.uri | http://dx.doi.org/10.1021/jo3025048 | |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society | |
| dc.subject | Reactivity Indices | |
| dc.subject | hydrogen bonding | |
| dc.subject | reaction coordinate | |
| dc.title | Reactivity indices profile: a companion tool of the potential energy surface for the analysis of reaction mechanisms. Nucleophilic aromatic substitution reactions as test case | |
| dc.type | Artículo |
Files
Original bundle
1 - 1 of 1
Loading...
- Name:
- Reactivity Indices Profile A companion tool of the potential energy surface for the analysis of reaction mechanims. Nucleophilic aromatic substitution reactions as test case.pdf
- Size:
- 1.92 MB
- Format:
- Adobe Portable Document Format
- Description:
- Texto completo