Chemical separations are an important part of an undergraduate chemistry curriculum. Sophomore students often get experience with liquid−liquid extraction in organic chemistry classes, but liquid−liquid extraction is not as often introduced as a quantitative sample preparation method in honors general chemistry or quantitative analysis classes. This experiment offers a relevant, interesting way to use liquid−liquid extraction and high-performance liquid chromatography (HPLC) to analyze popular lotions and creams for niacinamide content. After completing the experiment, students will have a better understanding of the extraction technique, Beer−Lambert law, and HPLC. The percent recovery from a spiked sample of Olay Original Active Hydrating Beauty Fluid was found to be 99.22% with a standard deviation of 0.01%.
In this Article, we present a new method for the synthesis of diarylnorbornadiene derivatives. Through the use of a two-step procedure consisting of a tandem alkene insertion-Suzuki coupling reaction followed by a DDQ dehydrogenation, we have been able to synthesize derivatives with a wide variety of substituents. We also present the results of UV-visible spectroscopy studies and kinetics experiments that show the effect of substituent on light absorption properties of the norbornadienes as well as the kinetic stability of the quadricyclanes that result from their photochemical conversion. While substitution on the aromatic rings had comparatively little effect on quadricyclane lability, substitution at a bridgehead position with a methyl group produced a quadricyclane that thermally reverted to the norbornadiene at a rate that was significantly slower than that for the quadricyclane without the methyl substituent. From the results of the kinetics experiments, we determined that the reversion of the quadricyclanes occurs via a free radical mechanism with very little contribution from polar effects. This observation led us to speculate as to whether our data may form the basis for a free radical substituent constant, σ•, analogous to the traditional Hammett σ parameter.
A chemical separation experiment can be an interesting addition to an introductory analytical chemistry laboratory course. We have developed an experiment to extract FD&C Red Dye #40 from beverages containing cranberry juice. After extraction, the dye is quantified using colorimetry. The experiment gives students hands-on experience in using solid phase extraction to extract the red dye from other colorants in the red beverages. Students are also given experience with colorimetry, the Beer−Lambert law, and some wet chemical techniques. The recovery of the red dye from spiked cranberry juice was found to be 99% with a standard deviation of 2%.
We report herein the synthesis and characterization of 9-(2-diallylaminoethyl) adenine. We evaluated two different synthetic routes starting with adenine where the optimal route was achieved through coupling of 9-(2-chloroethyl)adenine with diallylamine. The cyclopolymerization and cyclo-copolymerization of 9-(2-diallylaminoethyl)adenine hydrochloride salt resulted in low molecular weight oligomers in low yields. In contrast, 9-(2-diallylaminoethyl)adenine failed to cyclopolymerize, however, it formed a copolymer with SO2 in relatively good yields. The molecular weights of the cyclopolymers were around 1,700–6,000 g/mol, as estimated by SEC. The cyclo-copolymer was stable up to 226 °C. To the best of our knowledge, this is the first example of a free-radical cyclo-copolymerization of a neutral alkyldiallylamine derivative with SO2. These polymers represent a novel class of carbocyclic polynucleotides.
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