Chemistry Commons^™

Gas–Phase Studies Of C–H Activation And Dehydrogenation Of Liquid Organic Hydrogen Carrier Model Compounds, Robert S. King

Graduate Research Theses & Dissertations

In the transport of hydrogen, cryogenic methods are often utilized; however, this method is high in energy cost and not sufficiently safe in terms of release prevention. Liquid organic hydrogen carriers (LOHCs) are one of the many methods being developed for a robust and safe hydrogen energy infrastructure. One aspect of LOHCs with a rich research field as of late is dehydrogenation techniques to liberate stored hydrogen gas for energy consumption. This process currently requires excessive cost (environmental and monetary), specialty catalysts using expensive metals like palladium for the selective dehydrogenation without coking of the catalyst surface. In search for …

Determination Of Structural Factors Contributing To Protection Of Zinc Fingers In Estrogen Receptor Α Through Molecular Dynamic Simulations, Patricia B. Lutz, Wesley R. Coombs, Craig A. Bayse

Chemistry & Biochemistry Faculty Publications

The ERα transcription factor that induces tumor growth is a potential target for breast cancer treatment. Each monomer of the ERα DNA-binding domain (ERαDBD) homodimer has two conserved (Cys)₄-type zinc fingers, ZF1 (N-terminal) and ZF2 (C-terminal). Electrophilic agents release Zn²⁺ by oxidizing the coordinating Cys of the more labile ZF2 to inhibit dimerization and DNA binding. Microsecond-length molecular dynamics (MD) simulations show that greater flexibility of ZF2 in the ERαDBD monomer leaves its Cys more solvent accessible and less shielded from electrophilic attack by sulfur-centered hydrogen bonds than ZF1 which is buried in the protein. In the …

Phytochemical Analysis, Antioxidant, And Antibacterial Properties Of Partition Fractions Of Adansonia Digitata And Annona Muricata Extracts Using Chloroform, Ethyl Acetate, Ethanol, And Aqueous Solvent Systems, Fagbohun Oyenike Bushirat, Hassan Abdusalam Adewuyi, Sakariyau Adio Waheed, Maryam Nana Musa, Timothy God-Giveth Olusegun, Ayomide Babatunde Ishola, Agumage Idoko, Adeola Victor Kolawole, Adesanmi Adefunmilayo Oluwatuyi, Sarah Ngozi Agwasim

Chemistry & Biochemistry Faculty Publications

Adansonia digitata and Annona muricata are traditionally used medicinal plants with reported pharmacological properties. In this study, we aimed to elucidate the phytochemical composition, antioxidant activity, and antibacterial properties of partition fractions of Adansonia digitata and Annona muricata extracts obtained using chloroform, ethyl acetate, ethanol, and aqueous solvent systems. The plant extracts were successively partitioned using chloroform, ethyl acetate, ethanol, and aqueous solvent systems. Phytochemical analysis was performed using standard methods. Antioxidant activity was evaluated using FRAP and DPPH assays. Antibacterial activity was assessed using agar well diffusion and MIC determination. Phytochemical analysis revealed the presence of alkaloids (10.2-15.6%), flavonoids …

The Importance Of Solution Studies For The Structural Characterization Of The Enterovirus 5' Cloverleaf, Morgan G. Daniels, Meagan E. Werner, Xiaobing Zuo, Steven M. Pascal

Chemistry & Biochemistry Faculty Publications

Enteroviruses initiate genomic replication via a highly conserved mechanism that is controlled by an RNA platform, also known as the 5' cloverleaf (5'CL). Here, we present a biophysical analysis of the 5'CL conformation of three enterovirus serotypes under various ionic conditions, utilizing CD spectroscopy, size-exclusion chromatography, and small-angle X-ray scattering. In general, a tendency toward a smaller monomeric hydrodynamic radius in the presence of salts was observed, but the exact structural signature of each 5'CL varied depending upon the serotype. Rhinovirus B14 (RVB14) exhibited at least two monomeric conformations and a low propensity for dimerization, while poliovirus 1 (PV1) showed …

Design And Synthesis Of Organocatalyts For Efficient Decontamination Of Organophosphate-Based Nerve Agents And Pesticides, Emmanuel Kingsley Darkwah

Doctoral Dissertations

Exposure to organophosphate-based nerve agents and pesticides poses significant health and security threats to civilians, soldiers, and first responders. Despite extensive efforts to develop chemical detoxification agents for use in topical applications on exposed skin surfaces and for intravenous injections, there remains an unmet need for effective, non-hazardous decontaminating agents. The current state-of-the-art decontaminating agent, Dekon-139 (2,3-butanedione oxime, potassium salt), exhibits adverse effects when applied to the skin.

In this study, we designed and synthesized pharmaceutically relevant aminoguanidine-derived aldimines that are relatively non-toxic and substantially more effective at decontaminating nerve agents and pesticides compared to existing agents, and they act …

Products Of Laser Ablated Actinides And Actinide Comparators In The Presence Of Carbonyl Sulfide Characterized By Rotational Spectroscopy, Joshua Edward Isert

Doctoral Dissertations

As the consumption of energy continues to rise globally, so too has interest in alternative energy sources such as nuclear power. However, a fundamental understanding of the actinide series is needed in order to safely and efficiently utilize these elements. Rotational or microwave spectroscopy, depending on if one is speaking of the physical outcome of the experiment or the region of the electromagnetic spectrum being operated in, is a gas phase molecular study utilized for structural determination. This technique can be utilized to gain an in depth understanding of bonding within the actinide series. However, when studying species that are …

Tailoring Selected Aerogels To Targeted Applications, Stephen Yaw Owusu

Doctoral Dissertations

Aerogels are ultra-lightweight, porous solid materials characterized by a three-dimensional nanostructured network. Owing to their exceptional physical and chemical properties, aerogels have garnered considerable attention within the materials science community and were recognized by IUPAC in 2022 as one of the top ten emerging technologies in chemistry. Although numerous aerogels have been synthesized, only a few have been effectively tailored for specific applications. Optimizing the properties of known aerogels for targeted uses remains challenging. This dissertation investigates strategies for tailoring aerogels derived from isocyanate-benzoxazine, benzodiazine, and phenolic resins to meet the requirements of various advanced applications. The approaches employed include …

Unraveling Visible Spectra Of S-Type Stars: The F3Δ–A3Δ (Α System) And E3Π–A3Δ (Β System) Band Systems Of Zro, Manish Bhusal, Peter Bernath, Jacques Liévin

Chemistry & Biochemistry Faculty Publications

ZrO has many low-lying states, and its spectra are essential for the characterization of S-type stars. A high-resolution emission spectrum recorded with a Fourier transform spectrometer at the National Solar Observatory is used for the analysis. The 0–0 and 1–0 bands of the f³Δ-a³Δ system (α system) and the 0–0 band of the e³Π-a³Δ system (β system) have been rotationally analyzed using the modern spectral fitting program PGOPHER. New ab initio calculations of transition dipole moments have been performed to determine the band strengths. These band strengths are used to produce line lists that are suitable for the …

M Star Opacities: The B³Π–X³Δ Band System Of Tio, Peter F. Bernath, Manish Bhusal, Mirek R. Schmidt

Chemistry & Biochemistry Faculty Publications

The spectra of titanium monoxide (TiO) are used to classify M stars. TiO experimental cross sections based on a high-resolution emission spectrum recorded with a Fourier transform spectrometer at the National Solar Observatory are used for the analysis of the TiO B³Π–X³Δ transition (𝛾' system). The 3–2 and 4–3 vibrational bands are analyzed for the first time, and the analysis of the 2–1 band is revised. The transition dipole moment function from an ab initio calculation is used to calculate the band strengths. These band strengths are used to produce a B³Π–X³Δ line list for the vibrational levels v' ⩽ …

Introduction Of Polar Functional Groups To Pyridinedipyrrolide Zirconium Photosensitizers Through Post-Synthetic Modifications, Marisa Nicole Tordella

Graduate Theses, Dissertations, and Problem Reports (ETD)

Photosensitizers are vital components to applications such as photoredox catalysis, photodynamic therapy, and various avenues of solar energy production. The abilities of transition metal photosensitizers containing precious metals have been well studied over the years. However, because of the growing scarcity of these metals, there has been a shift in finding more earth abundant alternatives. To help fill this gap in the literature, the Milsmann group has developed and studied the photophysical properties of Zr(IV) complexes with various ligand systems. Due to the electron deficient metal center, these complexes exhibit ligand-to-metal charge transfer (LMCT), unlike the metal-to-ligand charge transfer commonly …

Catalytic Innovation For Sustainable Styrene Production: Green Chemistry Strategies Utilizing Octahedral Ruthenium (Ii) Complexes Supported By A Single Bipyridine Ligand, Kennedy G. Musso, Brandon Quillian, Clifford Padgett, Jose Jimenez

College of Graduate Studies: Theses & Dissertations

This study investigates: 1) the synthesis and reactivity of the mono- substituted systems, [κ²-(t-bipy)Ru(NCMe)2(Ph)(PR3)][BArF'] supported by different ancillary ligands PR3 = (P(OCH3)3 and P(CH3)3) and a single bidentate ligand, 4,4′-di-tert-butyl-2,2′-bipyridine (t-bipy), and 2) UV/heat formation of di-PR3 and tri-PR3 systems supported by a single bidentate ligand to better understand the mechanism of styrene production. Utilizing [(η6-p-cymene)RuI(µ-I)]2 (1), the complexes (η6-p-cymene)RuI2(P(OCH3)3) (2) and (η6-p-cymene)RuI2(P(CH3)3) (3) were synthesized and phenylated to produce (η6-p-cymene)RuI(Ph)(PR3) (6; PR3 = P(OCH3)3 and 7; PR3 = P(CH3)3). Complex 4, (η6-p-cymene)RuCl2(P(CH3)3), was also synthesized and phenylated to produce (η6-p-cymene)RuClPh(P(CH3)3) (5) to understand the impact of chloride versus iodine …

Analysis Of Gas Station Drugs Using Gas Chromatography Mass Spectrometry And Fourier Transform Infrared Spectroscopy, Megan Joos

All ETDs from UAB

Gas stations and head shops are a seemingly safe and legal marketplace for drug purchase. However, although marketed as dietary supplements or cognitive enhancers, the products sold there have been known to contain psychoactive substances which may be mislabeled or actually contain regulated substances. This study investigates the composition of such products, specifically those labeled as kratom and non-kratom Mitragyna species using gas chromatography-mass spectrometry (GC-MS) and those labeled as phenibut using GC-MS and fourier transform infrared spectroscopy (FTIR). Samples were acquired from retailers in the Birmingham, AL area. The products underwent both qualitative and quantitative analysis of their ingredients …

Metal-Free Photoredox Catalysis For The S-Trifluoromethylation Of Thiols And Investigation Of Ph-Dependent Decontamination Of Dimethyl Chlorophosphate, A Nerve Agent Simulant, Via Hydrolysis With Azoles, Raheemat Rafiu

Doctoral Dissertations

"Organofluorine chemistry plays a critical role in synthetic chemistry due to the unique properties of fluorine. However, the S-trifluoromethylation of thiols remains underexplored, with existing methods often relying on toxic and expensive organometallic catalysts. Given the advantages of S-trifluoromethylated compounds, including enhanced pharmacological activity and improved metabolic stability, we developed a green and cost-effective method for the synthesis of S-CF3 compounds using diacetyl as the organic catalyst and Langloi's reagent as the trifluoromethylating reagent. This reaction, which proceeds under mild conditions using visible light photoredox catalysis, works across various substrate scopes, including aromatic, heteroaromatic, and aliphatic thiols.

Chemical Warfare Agents …

Polybenzodiazine Aerogels: All-Nitrogen Analogues Of Polybenzoxazines - Synthesis, Characterization, And Their Application In Carbon Dioxide Capture, Vaibhav Edlabadkar

Doctoral Dissertations

"The rapidly risen concentration of carbon dioxide in the atmosphere over recent years contributed to global warming and ocean acidification. Carbon capture is viewed as an essential tool from keeping atmospheric CO₂ levels from rising further. This thesis focuses on the development of new materials for high capacity and selective adsorption of CO₂. One such material was based on a newly synthesized tetrahydroquinazoline (THQ), which was designed as an all-nitrogen analogue of main-stream benzoxazine monomers. THQ solutions in DMF gelled at 100 °C via HCl-catalyzed ring opening polymerization to polybenzodiazine (PBDAZ) wet gels, which were dried in …

Applications Of Tetramethyl-Guanidine Supported Cationic Transition Metal Sites Towards C─N Bond Construction Methodologies And [3+2] Cycloaddition Reactions, Suraj Kumar Sahoo

Doctoral Dissertations

"We present a family of divalent cationic bipodal and tripodal M(II) reagents (M = Mn, Fe, Co) supported by superbasic tetramethyl-guanidinyl (TMG) residue framework with applications towards C─N bond construction methodologies. These cationic reagents possess unique characteristics since their enhanced Lewis acidity facilitates in situ elaboration of the primary nitrene-transfer product (aziridine). Indeed, further aziridine-ring opening and cycloaddition of several dipolarophiles (nitriles, alkenes, ketones) permits the three-component synthesis of valuable five-membered N-heterocycles, commonly found in pharmaceuticals and agrochemicals.

We undertake a more systematic study to unravel parameters that make certain divalent metal sites more suitable as catalysts for the in-situ …

Development Of Dual-Scan Nuclear Magnetic Resonance (Nmr) Pulse Programs For Spin-Lattice Relaxation Measurements, Zachary Mayes

Doctoral Dissertations

This research develops and refines the Split Inversion Pulse and Recovery (SIP R) methodology for spin-lattice relaxation (T₁) measurements in NMR spectroscopy. SIP R introduces a two-scan difference technique using a split inversion pulse sequence, where the 180° pulse is split into two 90° pulses phase-shifted with respect to each other. This approach simplifies data fitting, requiring only two parameters to extract T₁ values, compared to the traditional inversion-recovery method, which needs three. The SIP-R-DS and SIP-R-S adaptations extend this framework by incorporating selective NMR resonance excitations, enhancing its applicability to cross-polarization experiments and enabling unobstructed NOE measurements. These adaptations …

Characterization And Optimization Of Sand And Tung Oil-Based Resins For Binder-Jet 3d Printing, Daniel I. Ajiola

College of Graduate Studies: Theses & Dissertations

Binder-jet 3D printing as a transformative technology in additive manufacturing, offers the ability to fabricate complex structures with diverse materials. This thesis investigates the use of a sustainable tung oil-based resin to create composites, exploring the potential for an eco-friendly alternative to synthetic binders.

The aim of this research is to develop and characterize a bio-based resin formulation, using tung oil as the primary binder, for application in binder-jet 3D printing with sand as the reinforcement. The resin formulation was prepared by combining tung oil, n-butyl methacrylate, divinylbenzene, and di-tert-butyl peroxide in precise proportions, ensuring a balanced mixture that supports …

Synthesis And Characterization Of A Biobased Polymer From Tung Oil And Pine Rosin & Characterization Of Polyhydroxybutyrate., Arijanet P. Osumah

College of Graduate Studies: Theses & Dissertations

This thesis presents two independents but thematically aligned research projects focused on the development and evaluation of sustainable polymers. The first involves the synthesis and characterization of a biobased polymer derived from tung oil and pine rosin. Tung oil, which is a triglyceride was chemically modified to produce tung oil diglyceride (TDG), which subsequently reacted with abietic acid-rich pine rosin to yield tung oil abietate (TOA), a biobased monomer. The TOA monomer was polymerized with butyl methacrylate (BMA) and divinylbenzene (DVB) using di-tert-butyl peroxide (DTBP) as a thermal initiator. The resulting polymer was thoroughly characterized using Fourier transform infrared spectroscopy …

Assessment And Health Benefit Of Vitamin C Using A549 Cell, Yetunde Adepoju

College of Graduate Studies: Theses & Dissertations

Vitamin C (ascorbic acid) is a vital micronutrient recognized for its antioxidant capacity and essential bodily functions, such as collagen formation, neurotransmitter activity, and regulation of the immune system. This study explores how vitamin C can protect and potentially heal cells under oxidative stress and inflammation, using A549 cells, a human lung epithelial cell line, as the model system. The cells were exposed to varying concentrations of vitamin C dissolved in water, DMSO, and 5% DMSO. To assess the outcome, cell viability was measured with an MTT assay. In addition, the expression of key genes related to oxidative stress and …

Cui-Derived Cuxo Thin Films Development Via Thermal Oxidation For Lead-Free Perovskite Solar Cells, Md Jakir Hossen, Md Shahinuzzaman, M. S. Jamal, Suhana Mohd Said, S. F.W.M. Hatta, Md Helal Miah, Mayeen Uddin Khandaker, Mohammad Nur-E-Alam, Mohammad Aminul Islam

Research outputs 2022 to 2026

The development of low-cost, stable, and efficient hole transport layers (HTLs) is crucial to the advancement of lead-free perovskite solar cells. In this work, a solution-based oxidation process is employed to convert spin-coated copper iodide (CuI) films into mixed-phase copper oxide (CuxO) thin films comprising Cu₂O and CuO. Oxidation occurs under moderate temperatures (200–300°C), leading to uniform, compact, and highly conductive p-type films with tunable bandgaps. Structural, morphological, and optical analysis confirms successful phase transformation, and measurements of Hall effect reveal maximum mobility of holes of 26.7 cm² V⁻¹ s⁻¹ for double-coated films annealed at 300°C. Device …

Lead-Free Alternatives And Toxicity Mitigation Strategies For Sustainable Perovskite Solar Cells: A Critical Review, Md Helal Miah, Mayeen Uddin Khandaker, Md Jakir Hossen, None Noor-E-Ashrafi, Ismat Jahan, Md Shahinuzzaman, Mohammad Nur-E-Alam, Mohamed Y. Hanfi, Md Habib Ullah, Mohammad Aminul Islam

Research outputs 2022 to 2026

The growing global energy demand has prompted an increase in research into renewable energy conversion technologies. Although lead-based perovskite solar cells (PSCs) offer high efficiency as well as low manufacturing costs, the toxicity of the material is still a serious hurdle to their commercialization and widespread adoption. Amid ongoing efforts to develop lead-free perovskites, over the last few years, growing attention on mitigating the toxicity of lead by inhibiting the leakage of lead from PSCs has been observed. This review discusses the potential replacement of lead from PSCs and explores various approaches to mitigate lead leakage from PSCs. In addition, …

Cloud Condensation Nuclei Activity Of Fresh And Aged Phenolic Acid Aerosol Particles, Emily A. Nortmann

Honors Undergraduate Theses

In recent years, the incidence of wildfires has considerably increased, with fire seasons starting earlier and ending later than usual due to changes in snowpack, precipitation, and temperature, which are attributed in part to climate change. Wildfires are responsible for the emission of a variety of gases and organic aerosol particles in the atmosphere with profound impacts on air quality, visibility, and human health. The aerosol particles produced by wildfires can contribute to climate change by scattering or absorbing solar radiation, affecting the radiative balance of the planet through cooling or warming effects, or by acting as cloud condensation nuclei …

Separation And Surface Examination Of Spacecraft Cabin Particulates, Grace A. Belancik

Master's Theses

Particulate matter in the atmosphere is a known detriment to human health, but several factors affect any particulate’s particular toxicity including particle size, surface area, and chemical composition. Extensive studies have been conducted to examine particulate hazards on Earth, but in crewed spacecraft, like the International Space Station (ISS), the particulate environment is wholly unique due to both the controlled environment and lack of gravity. Atmospheric sampling studies are underway, but another convenient source of airborne particulates for analysis is the contents of the vacuum bags used by the astronauts to clean the air vents. However, no method currently exists …

Photoswitchable Inhibitors Of Eaat3, Karly Suhr

Electronic Theses & Dissertations (2024 - present)

Azobenzene is a photoswitchable molecule known for its high conversion yield and repeatability. The inclusion of an azobenzene moiety with a known inhibitor of your target of interest allows for greater study of function as well as potential therapies. Three derivatives were designed from azobenzene and known inhibitor of EAATs, TBOA, to synthesize photoswitchable inhibitors of EAATs. Further investigation into the function of EAATs and development of a specific inhibitor for EAAT3, an important glutamate transporter in the brain required for proper function, can then be conducted. Photoisomerization studies on the derivatives were conducted using UV/vis spectroscopy and NMR spectroscopy. …

Modification Of Nanoparticles For Designed Interfaces, Tony Lee Neely, Jr.

Theses and Dissertations

The work contained herein, is focused on the design, synthesis, and characterization of polymer nanocomposite interfaces and the property enhancement afforded from said interface design. Through the use of reversible addition fragmentation chain transfer (RAFT) polymerization for the grafting of polymer chains to silica nanoparticles, the surface of silica nanoparticles can be manipulated to tune the properties of the nanocomposite as a whole.

In the first part of this work, heterogeneity is introduced onto the surface of silica nanoparticles via a sequential RAFT polymerization to afford a bimodal brush system. A densely grafted, short brush population is polymerized from the …

Calcium Carbonate Microparticles As Acid Responsive Targeted Drug Delivery Carriers For Oral Diseases And Its Anti-Bacterial Activity, Hem Raj Joshi

Dissertations and Theses

Dental diseases are mostly caused by bacterial infections in the teeth, forming biofilms that release acids and decay the enamel of the teeth. More than half of the world's population were affected by oral diseases, including periodontitis (gum disease), dental caries (cavities), and oral cancer. Chlorhexidine (CHX) is the mostly used antimicrobial drug for dental diseases, but its overexposure to the healthy teeth causes many side effects, such as tooth staining, taste alteration, and many more. Taking advantage of the acidic environment of infected teeth, we designed a pH responsive targeted drug delivery system using calcium carbonate microparticles (CCMPs) as …

A Potentially Fruitful Path Toward A Cleaner And Safer Environment: Mxenes Uses In Environmental Remediation, Ali Mohammad Amani, Milad Abbasi, Atena Najdian, Farzaneh Mohamadpour, Seyed Reza Kasaee, Hesam Kamyab, Shreeshivadasan Chelliapan, Hanieh Ardeshiri, Lobat Tayebi, Ehsan Vafa, Sarah Mosleh-Shirazi, Alireza Jahanbin, Saravanan Rajendran, Daniel Simancas-Racines

Electrical & Computer Engineering Faculty Publications

The rapid industrialization of the world has resulted in severe environmental pollution, necessitating the development of new materials such as pollution remediation. Two-dimensional (2D) MXenes have emerged as a promising family of materials due to their unique physicochemical properties, making them ideal for environmental remediation. The article sheds light on the new opportunities of MXenes in the removal of organic and inorganic contaminants, including organic dyes, pharmaceuticals, heavy metals, radionuclides, and gas pollutants. MXenes also show excellent performance in photocatalytic degradation, adsorption, and microbial inactivation with environmental safety. Moreover, their application in recovering valuable elements from waste streams is also …

Technological Development Of In-Cell Nmr: Microfluidic, Metabolomic, And Fluxomic Approaches, Nicholas Sciolino

Electronic Theses & Dissertations (2024 - present)

In the fields of structural biology, metabolomics, and fluxomics, there is a driving, technique-based concern when it comes to high-resolution spectrometry and its marriage to biological and physiological relevance. Sample preparation often involves cellular perturbation, lysate separation schemes, combinations with non-biological reagents, and timeline slack. Conceptually, the farther we get from the cell, the greater the potential disparity between what exists in vivo and our in vitro manipulations. This is particularly true when seeking to collect data on transfected targets of interest, and on sensitive metabolic equilibria that occur on the order of minutes. The question remains: if we are …

Development Of Catalytic Membranes And Composites For Energy Storage Devices And Nonenzymatic Biosensors, Harish Singh

Doctoral Dissertations

The excessive use of fossil fuels has led to their rapid depletion, causing an energy crisis and environmental issues. Consequently, there's a growing focus on sustainable energy conversion. Electrocatalysts are pivotal in this development, particularly for fuel cells and solar fuel generators, necessitating high-efficiency, cost-effective catalysts for large-scale adoption. Transition metal chalcogenides have emerged as promising electrocatalysts due to their high efficiency, electrochemical tunability, and abundant active sites. This work is divided in two parts. In Part A, we have investigated transition metal chalcogenide and few atom clusters FACs as electrocatalysts for oxygen evolution and reduction, highlighting their structure-property relationships …

Scope And Mechanism Of The Ruthenium-Catalyzed Sp3 C–H Coupling Reaction Of 2-Alkylindoles With Enones For The Synthesis Of Carbazole Derivatives, Krishna Prasad Gnyawali, Mina Son, Donghun Hwang, Nuwan Asanka Pannilawithana, Mu-Hyun Baik, Chase S. Yi

Chemistry Faculty Research and Publications

The catalytic system consisting of a cationic Ru–H complex 1 and 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for the dehydrative sp³ C–H coupling reaction of 2-alkyl substituted indoles with enones to form 2,4-disubstituted carbazole products. The analogous coupling reaction of 2-alkylindoles with linear enones bearing the cyclic olefinic group afforded tetracyclic carbazole products. A normal deuterium kinetic isotope effect was measured from the coupling reaction of 1,2-dimethylindole versus 1-methyl-2-(methyl-d₃)indole with (E)-3-penten-2-one (k_H/k_D = 2.5). The Hammett plot was constructed from the reaction of para-substituted …