Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
نویسندگان
چکیده
We describe here the determination of the alkylation rate of a set of organic superbases by iodomethane in DMF using a microfluidic continuous flow reactor. Surprisingly, log k(Alkylation) follows the inverse trend of pK(BH+) of the base. Mayr's equation allows a more quantitative approach. From a synthetic point of view, TMGN and BEMP are demonstrated to be the best choices.
منابع مشابه
Simultaneous solvent screening and reaction optimization in microliter slugs.
An automated, continuous flow droplet screening system is presented, enabling real-time simultaneous solvent and continuous variable optimization. An optimal design of experiments strategy is applied to the alkylation of 1,2-diaminocyclohexane in 16 μL droplets, with scale-up demonstrated. Analysis of segmented flow results suggests correlation of yield with solvent hydrogen bond basicity.
متن کاملNumerical Study of Droplet Generation Process in a Microfluidic Flow Focusing
Microfluidic flow focusing devices have been utilized for droplet generation on account of its superior control over droplet size. Droplet based microfluidics addressed many scientific issues by providing a novel technological platform for applications such as biology, pharmaceutical industry, biomedical studies and drug delivery. This study numerically investigated the droplet generation proce...
متن کاملN-Methylation of 2-Furylhenzothiazoles. The Influence of Substituents on the Rate of Quaternizationa,b
Recently we reported the preparation and properties of some 2-(2or · 3-furyl)benzothiazoles1• Like many other thiazoles2 , due to their weak basic character they can give quaternary salts. Comparing 2-(2-methyl-3-furyl)benzothiazoles with the 2-(5-methyl-2-furyl) analogue it was observed that the nucleophilicity (and basicity) of benzothiazole nitrogen is influenced by the position of the methy...
متن کاملMicrofluidic extraction of tannic acid from Quercus leaves
In this study, extraction of tannic acid using microchannel was investigated. Affective parameters were optimized. Different solvents including buthanol, ethylacetate and n-hexane as organic phase, methanol, propanol, ethanol and water as aqueous phase investigated. Microchannels with different confluence angles and diameters were examined. Microchannels with different confluence angles and dia...
متن کاملMeasurement of enzyme kinetics using a continuous-flow microfluidic system.
This paper describes a microanalytical method for determining enzyme kinetics using a continuous-flow microfluidic system. The analysis is carried out by immobilizing the enzyme on microbeads, packing the microbeads into a chip-based microreactor (volume approximately 1.0 nL), and flowing the substrate over the packed bed. Data were analyzed using the Lilly-Hornby equation and compared to value...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 10 40 شماره
صفحات -
تاریخ انتشار 2012