Organic Chemistry Commons^™

Evaluating The Nash Reaction As A Sustainable Alternative To The Snar Reaction In The Synthesis Of Pharmaceutical Intermediates, Allison L. Ryerson, James K. Bashkin, Jessica R. N. Thompson, Adam Weiss, Huy Q. Nguyen

Undergraduate Research Symposium

Nucleophilic aromatic substitution (SNAr) reactions are one of the most widely used reaction classes in pharmaceutical production today, used for example to produce nitroaryl amine intermediates. In comparison to the traditional SNAr pathway, the nucleophilic aromatic substitution of hydrogen (NASH) provides a greener alternative in pharmaceutical production by using cheaper starting materials, eliminating more hazardous solvents, and reducing toxic waste.

Synthesis And Charge Transport Characterization Of 9,9'-Bifluorenylidene-Based Conjugated Molecules For Single-Molecule Conductance, Zach Moughamian, Jahnavi Badiganti, Jinjia Xu

Undergraduate Research Symposium

Molecular electronics explores the use of individual molecules as functional components in nanoscale electronic devices. In this project, fluorenone-based π-conjugated molecules including 9,9'-bifluorenylidene-S and triphenylamine-substituted derivatives were synthesized to investigate structure-property relationships relevant to molecular charge transport. The synthesized compounds were obtained in 13% and 27% yield respectively. ¹H NMR spectroscopy confirms characteristic aromatic resonances in the 7-9 ppm region consistent with the conjugated framework. UV–Vis spectroscopy reveals absorption maxima at 459 nm and 470 nm, indicating extended π-conjugation and donor-acceptor effects. Single-crystal X-ray diffraction confirms the structure of 9,9'-bifluorenylidene-S, which crystallizes in the monoclinic system (space group P2₁/c). In …

Enantioselectivity Of The Photochemical Continuous-Flow Isomerization Of Humulones, Gregory M. Giovine, Trevor Smith, Bruce Hamper

Undergraduate Research Symposium

Humulones, the primary natural product present in the historically significant hop flower, represent a largely unexplored candidate for structure-based pharmaceutical design.  Showing promising biological activity as an anti-bacterial and anti-inflammatory agent, humulones are of interest both for their bioactive properties and for their long-established tolerability and natural abundance.  Humulones undergo a characteristic isomerization reaction, where the six-membered substituted phloroglucinol ring contracts to a five-membered ring isohumulone, under a variety of conditions, including those enabled by brewing conditions (thermal, metal-catalyzed) and by exposure to UV light.  Optimization of the photocatalyzed isomerization of n-humulone to n-isohumulone in flow conditions resulted in a …

Catalytic Synthesis Of Protoberberine Alkaloids And Their Evaluation As Selective Dopamine Receptor Ligands, Ashok Reddy Gudipally

Dissertations, Theses, and Capstone Projects

Dopamine regulates motor control, cognition, reward, motivation, and neuroendocrine signaling. Disruption of dopaminergic neurotransmission is closely linked to central nervous system disorders, including Parkinson’s disease, schizophrenia, addiction, and related neuropsychiatric conditions. Because these functions are mediated by multiple dopamine receptor subtypes with distinct roles in physiology and disease, the discovery of subtype-selective ligands remains an important goal in neuropharmacology. Within this context, protoberberine alkaloids, particularly tetrahydroprotoberberines (THPBs), are attractive molecular frameworks because they combine structural complexity with broad biological relevance, including measurable activity in CNS-related diseases. Prior work from our laboratory and others established (–)-stepholidine (1.60) as an important lead …

Multicomponent Reaction-Initiated Synthesis Of Polyheterocyclic Compounds, Ashutosh Nath

Graduate Doctoral Dissertations

Efficient synthesis of novel heterocycles with biological interest remains a challenge in modern organic chemistry. This dissertation presents the development of efficient synthetic strategies that combine multicomponent reactions (MCRs) with sequential reactions for rapid access a diverse array of polyheterocyclic compounds. The projects are: 1) Groebke-Blackburn-Bienaymé (GBB) reaction followed by N-acylation and Friedel-Crafts (FC) cyclization for the construction of imidazopyridine- and indole-fused azepinones involving an unusual ring-expansion process. 2) Modified GBB condensation products for intramolecular Diels-Alder (IMDA) cycloaddition and dehydrative re-aromatization to access imidazopyridine-fused isoquinolinones. 3) Integration of the Ugi-three component reaction (Ugi-3CR) and Pictet-Spengler (PS) reaction followed by …

Techniques, Skills, And Synthesis For “Cooking” In The Organic Laboratory, Emily C. Sylvester, Tim Evans

Open Education Materials

Lab manual for CHEM 211L, Organic Chemistry I Laboratory. Provides background and procedures for laboratory experiments, including fundamental techniques and several organic syntheses.

Creative Commons attribution.

Isolation Of Lavender Compounds Via Steam Distillation, Emma Norris, Gwendolyn Flippin

Discovery Day - Daytona Beach

Steam distillation was used to extract (R)- Linalool, Linalyl acetate, and Camphor from lavender during the steam distillation experiment. The compounds were extracted via a steam distillation apparatus. A 250 mL two-neck round-bottom flask, a thermometer adapter, 25 mL a thermometer, a condenser, a distillation head, a vacuum adapter, lab jacks, and clamps made up the apparatus. Then the lavender was massed out and added to a beaker with 100 mL of water. Over time, the distillate is collected in a vial to be analyzed. (R)- Linalool is a nonaromatic alcohol containing two alkenes with the chemical formula C_10 H_18 …

Chemical Profiling Of Star Anise (Illicium Verum) Via Gc–Ms: Identifying Compounds With Pharmaceutical Potential, Legacy Wilson, Yegor Bushnev

Discovery Day - Daytona Beach

Title: Chemical Profiling of Star Anise (Illicium verum) via GC–MS: Identifying Compounds with Pharmaceutical Potential   Abstract: Star anise (Illicium verum) has been used for both medicinal and culinary applications due to its diverse bioactive compounds. It is a primary natural source of shikimic acid (𝐶7𝐻10𝑂5), a key precursor in the synthesis of the antiviral drug oseltamivir (Tamiflu), used to treat influenza. Additionally, star anise has been used to treat respiratory and digestive conditions and is widely used for flavoring due to its licorice-like aroma, mainly from trans-anethole (𝐶10𝐻12𝑂) , its major component. Previous studies have also demonstrated mild central nervous …

Extracting Aromatic Compounds From Dehydrated Rose Buds, Lana Sheridan

Discovery Day - Daytona Beach

Eugenol (C10H12O2), methyl eugenol (C11H14O2), and 2-phenylethanol (C8H10O) are chemically aromatic, natural compounds commonly present in various botanical sources and essential oils. Structurally, eugenol is a methoxyphenol bearing an allyl side chain; its methyl ether derivative, methyl eugenol, shares a similar framework but features a methoxy group replacing the free phenolic hydroxyl group found in eugenol. 2-Phenylethanol is an aromatic alcohol comprised of a benzene ring linked to an ethanol moiety. The objective of this project was to isolate and characterize these compounds in dried rose buds using distillation followed by chromatographic and spectrometric analysis. For the experiment, a steam …

Steam Distillation Star Anise, Makayla Maso, Kiara Maso

Discovery Day - Daytona Beach

Star anise (Illicium verum) contains several volatile organic compounds responsible for its characteristic aroma, including trans-anethole, estragole, limonene, and linalool. These compounds differ in structure and chemical properties, which influence their behavior during isolation and analysis. Trans-anethole and estragole are classified as aromatic phenylpropene derivatives that contain benzene rings and ether functionalities. In contrast, limonene and linalool are non-aromatic terpenes, with linalool additionally possessing an alcohol functional group. These compounds are widely utilized as flavoring agents and fragrance components, while terpenes such as limonene and linalool are also commonly employed as solvents and in formulation chemistry due to their volatility …

Extraction Of Cedarwood Essential Oils Via Steam Distillation, Forrest Dohner

Discovery Day - Daytona Beach

Many natural materials, including pine and eucalyptus, produce distinct scents due to the presence of volatile organic compounds. In cedarwood, this aroma arises from a combination of aromatic molecules, which are organic compounds containing conjugated carbon ring systems that interact with olfactory receptors. Specifically, cedarwood contains three primary compounds responsible for its scent: cedrol, cedrene, and thujopene. The objective of this experiment was to extract these essential oils from cedarwood and identify their chemical composition. Steam distillation was used to isolate the volatile components by passing steam through the cedarwood, causing the essential oils to vaporize at temperatures below their …

Production And Analysis Of Lavender Essential Oil: Extraction, Composition, And Applications, Mary Zoeller

Discovery Day - Daytona Beach

Steam distillation was performed to extract essential oil from lavender and analyze its chemical composition. Lavender is known to contain several compounds such as linalool, terpinen-4-ol, and linalyl acetate, which contribute to its characteristic aroma and biological activity. The purpose of this experiment was to isolate these compounds without decomposition and identify them using gas chromatography–mass spectrometry (GC-MS). Approximately 14.851 g of lavender was heated with water to generate steam, which carried the volatile compounds into a condenser where the vapor was cooled and collected. The distillate was transferred to a separatory funnel to isolate the organic layer from the …

Steam Distillation Of Jasmine, Mikayla Hulvey, Meliah Martin

Discovery Day - Daytona Beach

This experiment aimed to isolate various components, including benzyl acetate, linalool, indole, and farnesene, from jasmine buds. The functional groups include an ester in benzyl acetate, an alcohol in linalool, an amine in indole, and alkenes in farnesene. Jasmine buds were combined with distilled water and steam distilled using a standard distillation apparatus. The distillate, containing hydrosol and trace amounts of essential oil, was then collected for extraction using methyl tert-butyl (MTBE) for a liquid-liquid extraction. The organic layer was then separated, washed using brine, dried over anhydrous sodium sulfate, and then transferred for later analysis. The essential oil obtained …

Developing Solvent Tolerant Microbial Membranes: Lipid Extraction And Laurdan Fluorescence Approaches For Biofuel Optimization, Gladstone Anku

Electronic Theses and Dissertations

The high demand for sustainable energy has increased interest in advanced biofuels, though production is limited by solvent toxicity to microbial hosts. This study investigated the role of lipid composition in modulating membrane fluidity and solvent tolerance using Bacillus subtilis as a model organism. Five strains were cultured, and membrane lipids were extracted and analyzed using thin-layer chromatography and gas chromatography–mass spectrometry; however, inconsistent results limited compositional characterization. To address this problem, reconstituted vesicles composed of phosphatidylglycerol (PG) and phosphatidylethanolamine (PE) were used as model membranes. Membrane fluidity was assessed using Laurdan fluorescence spectroscopy by measuring generalized polarization (GP) values …

Solvent-Free Ball-Milling Synthesis Of 1,2-Disubstituted Benzimidazoles, Zachary A. Jaffery, Katherine E. Christopher, Kyle A. Grice

DePaul Discoveries

The search for sustainability in chemistry has led to the development of the field of Green Chemistry, comprised by 12 guiding principles. Existing syntheses of benzimidazoles, a heterocycle widely used in medicinal chemistry, utilize methods with much room for improved sustainability. This work presents a solventless mechanochemical synthesis of 1,2-disubsituted substituted benzimidazoles from the condensation of phenylenediamines and aryl aldehydes. The effect of milling aid on yield and selectivity was investigated and montmorillonite K10 was determined to be the best milling aid. The purification protocol was optimized as well, with a heptane:EtOAc extraction and subsequent recrystallization from EtOH found to …

Recent Advances In Phosphatidylinositol Phosphate Kinases (Pipks) And Their Inhibitors, Mengxia Sun, Jian Hu, Xuefei Huang

BAU Journal - Science and Technology

Phosphatidylinositol phosphate kinases (PIPKs) are an important class of enzymes in humans, which produce lipid signaling molecules playing central roles in pathogenesis of diseases such as cancer, neurodegenerative diseases, and viral infection. Consequently, they are attracting increasing attention as drug targets for disease treatment. This review summarizes the functions of the PIPK family enzymes and highlights recent efforts on designing novel inhibitors against PIPKs. These advances are extensively discussed to stimulate interest in this field and promote further development of highly potent and selective inhibitors for innovative therapeutic applications.

Regioselective Tellurination Reactions And Their Utilities, Itunu Comfort Olanrewaju

Masters Theses

This thesis provides a comprehensive study of regioselective tellurination and its applications by integrating experimental and computational techniques, with an aim of synthesizing libraries of organotellurium heterocycles. This study addresses existing challenges in regioselective tellurination, such as unpredictable regioselectivity and avoidance of toxic reagents by harnessing intramolecular Te…O coordination and electrophilic aromatic tellurination. This strategy enables the development of previously poorly accessible compounds including benzotellurazinones, 2-acylaminobenzotellurazoles, and previously unknown 2,3-dihydrobenzo [b] oxatelluranes, which were prepared by antiMarkovnikov anti-addition of TeCl4 to C-C triple bonds. Experimental studies were complemented by computational DFT analyses to provide mechanistic and energetic insight into the …

Oer Organic Chemistry I Lab Manual, Ji Kim

Open Educational Resources

This Organic Chemistry I Lab Manual presents ten inquiry-based modules that integrate green chemistry principles into every stage of the microscale laboratory experience. Students use Kontes microscale glassware to perform essential techniques, including distillation, recrystallization, extraction, chromatography, and nucleophilic substitution reactions. Each module features standardized learning objectives, pre-lab questions, microscale procedures, data tables, and post-lab analysis. Green Chemistry Connections explicitly links each experiment to the Twelve Principles, emphasizing waste prevention, safer solvents, renewable feedstocks, and accident reduction. From isolating caffeine from tea and lycopene from tomato paste to synthesizing cyclohexene via E1 elimination, students learn classical organic chemistry through an …

Biomedical Applications Of Structurally Defined Natural And Semi-Synthetic Saponins, Chaeeun Lim-Paik

ETDs from 2020-2029

Triterpenoid saponins are amphiphilic glycosides that exhibit a wide range of biological and pharmacological properties, including antifungal, antiviral, molluscicidal, hypoglycemic, and hypocholesterolemic effects. These biological and pharmacological properties make saponins attractive for diverse applications. In this work, we demonstrate three biological applications: (i) immunostimulant vaccine adjuvant, (ii) protein delivery enhancement, and (iii) gene transfection enhancement. In light of the strong structure dependence of saponin activity, expanding the structural diversity of available scaffolds is essential for establishing structure-activity relationships (SAR) across these applications. Here, we expanded our saponin collection through semi-synthetic derivatization and the isolation of new saponins from distinct natural …

Computer-Aided Development Of Novel Antioxidants, Rita Bernadett Vlocsko

Graduate Doctoral Dissertations

Physiological redox homeostasis is a fine balance between prooxidants and antioxidants that are integrated elements of several reduction-oxidation mechanisms at molecular, organellar, cellular and tissue levels. When this equilibrium is disrupted and prooxidants become dominant, the body relies on endogenous and exogenous antioxidants to counterbalance the dysregulation and ultimately prevent the progression of oxidative stress. Reactive species (reactive oxygen species, reactive nitrogen species, or reactive sulfur species) are significant contributors to prooxidant activity. Over the years, substantial knowledge has been accumulated regarding their origin and roles in disease development, leading to the discovery and development of antioxidants that effectively target …