A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab

Wade, Peter A.; Rutkowsky, Susan A.; King, Daniel B.

doi:10.1021/ed083p927

Cited by 18 publications

(22 citation statements)

References 6 publications

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“…This method then is named solvent dropped grinding assisted crystallization (SDGR). Next, the mixture was crystallized using a slow evaporation method at 6–12°C/1 Atm/RH 72%, followed by direct cocrystallization using the Fischer reaction [8], named as FR method, which was performed using a similar procedure for ethyl diclofenac with 95% ethanol as the solvent. The existence of water maintains the equilibrium state between ethyl diclofenac with diclofenac acid, which was then expected to form cocrystals after the solvent has evaporated.…”

Section: Methodsmentioning

confidence: 99%

“…Salts may also be produced with this cocrystal besides esters [6, 7]. During esterification, the presence of water can disturb the process, causing a reversible reaction between the product and educt, namely, the Fischer equilibrium reaction [8]. When the mixture is recrystallized, intermolecular bonds are constructed and co-arranged into a new solid phase.…”

Section: Introductionmentioning

confidence: 99%

“…The EDDA crystal was constructed using two methods. The first method involved solvent-drop grinding, followed by recrystallization (SDGR) [16, 18, 19], while the second was a combination of Fischer reaction esterification and cocrystallization (FR) [5, 6, 7, 8].…”

Section: Introductionmentioning

confidence: 99%

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Cocrystal construction between the ethyl ester with parent drug of diclofenac: structural, stability, and anti-inflammatory study

Nugrahani

Utami

Nugraha

et al. 2019

Heliyon

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This study aimed to collect the crystallographic data of ethyl diclofenac and discover a cocrystal from this ester with its parent, diclofenac acid, and to investigate their physicochemical properties and anti-inflammation activity. Firstly, ethyl diclofenac single crystal was isolated and continued by the cocrystal screening and isolation. Solid characterization was conducted by thermal analysis, infrared spectroscopy, powder x-ray diffractometry, followed by structural determination using a single crystal x-ray diffractometer. The stability of the cocrystal toward heating and high humidity, followed by the anti-inflammatory activity, was also studied. Ethyl diclofenac and the cocrystal were successfully isolated and subsequently subjected to lattice system determination. Interestingly, the new cocrystal can be generated directly by Fischer equilibrium reaction during esterification of diclofenac acid. Structurally, ethyl diclofenac reveals a P21/c monoclinic and the cocrystal between this ester with its parent drug is a P-1 triclinic system. A hydrophobic interaction-C-Cl-, which is rarely found in a cocrystal, involved in the molecular interaction between ethyl diclofenac and the parent drug, besides the hydrogen bonds. The newly isolated cocrystal has a melting point AE103-104 C, which is higher than that of ethyl diclofenac (AE67.5 C) but lower than that of diclofenac acid (AE173 C). Hence, this cocrystal is stable towards accelerated stability testing by heating in a microwave, as well as storing in high relative humidity. Moreover, the antiinflammation test also showed promising activity improvement.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cocrystal construction between the ethyl ester with parent drug of diclofenac: structural, stability, and anti-inflammatory study

Nugrahani

Utami

Nugraha

et al. 2019

Heliyon

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“…4. Estudiar los efectos estructurales, de resonancia, inductivos y/o estéricos de diferentes sustituyentes, sobre la reactividad de un grupo funcional en una familia de moléculas, en una reacción dada, a través del diseño de problemas adecuados y el uso de la química combinatoria (Birney y Starnes, 1999;Duarte et al 2004y Wade et al, 2006) y la aplicación de diferentes escalas de trabajo (Pavia et al, 1990).…”

Section: El Método Propuestounclassified

Enseñanza Experimental y Química Combinatoria: Obtención de Esteres y Amidas, utilizando dos Fuentes de Energía Térmica y Microondas

Santos¹,

Lejarazo²,

Vilchis‐Reyes³

et al. 2011

Form. Univ.

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Se han diseñado una serie de experimentos de laboratorio con el fin de permitir a los alumnos resolver problemas para que a través del trabajo experimental individual y el trabajo en equipo utilizando las bases de la química combinatoria. Se ha usado la síntesis de ésteres del ácido paminobenzoico con alcoholes primarios con un número de átomos de carbono creciente y alcoholes ramificados para ver cómo se modifica la reactividad. Además se exploró el efecto que tiene el utilizar dos fuentes de energía: el calentamiento por conducción y el uso de microondas. Por otro lado, se realizó la síntesis de acetanilidas con p-aminofenol o anilina con el fin de comparar la reactividad de las aminas aromáticas. Los estudiantes desarrollaron aptitudes críticas del laboratorio de química orgánica y aumentaron sus habilidades del trabajo en equipo.

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“…Esterification reactions catalyzed by lipase to synthesize isoamyl and geranyl ester derivatives in a solvent-free system were used as a model for the study. Generally, esterification is a vital experiment that science students are required to learn. , Therefore, there are many esterification laboratory experiments for undergraduate students, including both science and nonscience majors, to help them learn this concept, especially esterification to synthesize flavors and fragrances compounds. − Most experiments use an acid-catalyzed reaction, − ,− in which the catalyst is not typically recovered and reused. During recent years, some greener esterification experiments have been developed that use microwave-assisted esterification and reusable catalysis. , However, there is no chemistry education lesson using an enzyme as a green catalyst to catalyze esterification, and thus, we lack a good example of the use of enzyme-catalyzed esterification to introduce the concept of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Lipase-Catalyzed Esterification: An Inquiry-Based Laboratory Activity To Promote High School Students’ Understanding and Positive Perceptions of Green Chemistry

2019

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An inquiry-based laboratory learning unit was designed to enhance high school students' understanding of the application of lipase as a catalyst to synthesize isoamyl and geranyl ester derivatives as well as to promote their understanding and positive perceptions of green chemistry. The learning unit consisted of three laboratories and a final presentation. The first laboratory activity allowed students to learn how to adjust macroscale titration techniques to microscale titration techniques so that the method could be used for quantitative determination of ester products in the next two laboratory activities. The second laboratory activity introduced students to a greener way to synthesize ester compounds by replacing a harmful strong acid catalyst with a more environmentally friendly catalyst, an enzyme lipase. The third laboratory activity challenged students to design their own experiments to synthesize other esters using lipase-catalyzed esterification reactions. At the end of the learning unit, students in each group presented the results and conclusions of the third laboratory activity to the whole class and explained how the 12 principles of green chemistry were applied in the laboratory. The results from the Learning Unit Conceptual Test and Learning Unit Perceptions Questionnaire indicate that the learning units can promote students conceptual understanding. They also have positive perceptions toward green chemistry and learning units.

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A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab

Cited by 18 publications

References 6 publications

Cocrystal construction between the ethyl ester with parent drug of diclofenac: structural, stability, and anti-inflammatory study

Cocrystal construction between the ethyl ester with parent drug of diclofenac: structural, stability, and anti-inflammatory study

Enseñanza Experimental y Química Combinatoria: Obtención de Esteres y Amidas, utilizando dos Fuentes de Energía Térmica y Microondas

Lipase-Catalyzed Esterification: An Inquiry-Based Laboratory Activity To Promote High School Students’ Understanding and Positive Perceptions of Green Chemistry

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