Site activation effects promoted by intramolecular hydrogen bond interactions in SNAr reactions?
RSC Advances Pub Date: 2014-07-02 DOI: 10.1039/C4RA04725G
Abstract
The nucleophilic aromatic substitution reaction of benzohydrazide derivatives towards 2-chloro-5-nitropyrimidine is used as model system to experimentally and theoretically show that intramolecular hydrogen-bond formation operates as a perturbation that elicits a dual response at the reaction center of the transition state (TS) structure, by enhancing the electrophilicity of the pyrimidine moiety and the nucleophilicity of the nitrogen atom of the benzohydrazide fragment. The electronic mechanism can therefore be described as a (non-local) site activation problem.
Recommended Literature
- [1] An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon SongPhys. Chem. Chem. Phys., 2014,16, 5295-5300 10.1039/C3CP54624A
- [2] An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction? Sandip Gangadhar Balwe,Yeon Tae JeongOrg. Biomol. Chem., 2018,16, 1287-1296 10.1039/C7OB02933K
- [3] An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs) R. M. Pemberton,J. P. Hart,T. T. MottramAnalyst, 2001,126, 1866-1871 10.1039/B104874K
- [4] An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage Mark D. Allendorf,Alauddin Ahmed,Tom Autrey,Jeffrey Camp,Eun Seon Cho,Maciej Haranczyk,Abhi Karkamkar,Di-Jia Liu,Katie R. Meihaus,Iffat H. Nayyar,Roman Nazarov,Donald J. Siegel,Vitalie Stavila,Jeffrey J. Urban,Srimukh Prasad Veccham,Brandon C. WoodEnergy Environ. Sci., 2018,11, 2784-2812 10.1039/C8EE01085D
- [5] An investigation of the electrochemical delithiation process of carbon coated α-Fe2O3nanoparticles Adrian Brandt,Florian Winter,Sebastian Klamor,Frank Berkemeier,Jatinkumar Rana,Rainer P?ttgen,Andrea BalducciJ. Mater. Chem. A, 2013,1, 11229-11236 10.1039/C3TA11821E
- [6] An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives? James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. HarrityChem. Commun., 2010,46, 5154-5156 10.1039/C0CC01345E
- [7] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [8] An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation?? M. Sheykhan,S. Khani,S. Shaabanzadeh,M. JoafshanGreen Chem., 2017,19, 5940-5948 10.1039/C7GC03141F
- [9] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
- [10] An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting? Lab Chip, 2019,19, 524-535 10.1039/C8LC01170B
Journal Name：RSC Advances
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)