Archive

Previous Molecules of the Week:

Perfluorooctanoic Acid

Perfluorooctanoic acid, or PFOA, is a useful industrial surfactant, meaning that it is used to decrease surface tension of water. It is also used as a material feedstock. PFOA is used in a vast number of places and products including clothes, furniture, waxes, and more, and it does its intended job quite well. The small problem with PFOA is that, like other per and poly fluoroalkyl substances (PFAS), it is a forever chemical, meaning it almost never breaks down. This is largely due to the carbon-fluorine bond, one of the strongest single bonds known. PFOA is also a potential (and likely) carcinogen. Combined with the previously discussed bioaccumulation as a forever chemical, it is easy to see why this and similar compounds are being phased out.

EDTA (Ethylenediaminetetraacetic Acid)

Ethylenediaminetetraacetic acid, or EDTA, is an incredibly useful ligand, meaning it binds to metal atoms to form a coordination complex. Due to the abundance of lone pairs on this molecule, once deprotonated, it is a hexadentate ligand, meaning it forms an incredible 6 bonds with a central metal atom/ion. Thus, EDTA can effectively sequester metal ions from solution and lock them away tightly in a coordination complex, preventing any reactions with the metal. Examples of this being useful are abundant. It is used in chelation therapy to treat lead poisoning, in the paper industry to prevent metal ions from helping hydrogen peroxide break down into water and oxygen, as a water softener in agriculture and laundry, and in many other applications and fields. Although not super harmful, its usage is being questioned because it breaks down very slowly in the environment. Mainly, it degrades under UV light, although bacteria that can break down specific EDTA-metal complexes have been discovered.

Melamine

Melamine has a few uses in the plastics and polymers industries for making resins, foams, plasticizers, laminates, and more. Melamine also appears in the structures of a few important drugs, like melarsoprol, which is used to treat African sleeping sickness. However, the most notable aspect of melamine is the fact that it is extraordinarily nitrogen-rich (66% by mass). As a result, it has gained infamy for being added to food as a form of doping. Basically, many tests used to assess the protein content of food rely on measuring nitrogen content because proteins are made of amino acids and linked by amides, resulting in most of the nitrogen of food being in proteins. Thus, when melamine is added to foods, like in the 2008 Chinese milk scandal, it makes it seem like the protein content is much higher. It is then possible to water down the product or sell a less-healthy version while making it seem protein-rich. Not only is this very unethical, melamine is toxic and when consumed, leads to crystal formation in the kidneys which causes severe kidney and bladder damage.

2,3,7,8-Tetrachlorodibenzo-p-dioxin

2,3,7,8-Tetrachlorodibenzo-p-dioxin, also known as TCDD, is an infamous pollutant, toxin, and cancer promoter. TCDD first gained infamy as a contaminant in Agent Orange, leading to a vast number of Vietnamese people being exposed to it. Despite the relatively low concentration of TCDD, health effects including a large number of cancers and birth defects have been observed in the years since. TCDD is not directly carcinogenic except in high doses, but it acts as a cancer promoter. This means that the effects of any other carcinogens in someone are increased, often substantially, leading to cancer. TCDD has also served as a serious pollutant also due to low level contamination. For example, the town of Times Beach, Missouri, was polluted with TCDD after dirt roads were sprayed with waste oil containing traces of it. The town became a Superfund site, was evacuated, cleaned, and is now a ghost town although it is now safe. TCDD serves as an important reminder of the impact of contaminants on people and the environment. In neither of the cases above was TCDD an intended product but it still was present in the low ppm ranges. Our understanding of TCDD and similar compounds continues to grow which will hopefully lead to fewer exposures, better cleanups, and better treatment for victims. In the meantime, it is important we understand the danger of these incredibly dangerous contaminants. For more information, I highly recommend this NIOSH publication: https://www.cdc.gov/niosh/docs/84-104/default.html

Atrazine

Atrazine is a controversial 1,3,5-triazine herbicide. Interestingly, we have already seen this structure a few weeks back with melamine, which is a 1,3,5-triazine with amines on the 2,4, and 6 carbons. This structural motif means that atrazine and similar compounds shut the electron transport chain down in plants by binding to the protein plastoquinone normally binds to. Because humans and other animals lack this, we are immune from this effect. However, there is some evidence that atrazine carries a few other negative effects in humans and animals. Studies like Hayes, Tyrone B et al. (2010) suggest that atrazine is an endocrine disruptor and can feminize African clawed frogs. However, this study has been criticized for flaws in the experimental design and has not been replicated. There is also some fear that atrazine may be teratogenic or carcinogenic. This has also not been proven. Although banned in Europe, the EPA has reviewed the compound multiple times and concluded that if there are urgent risks they will take action on atrazine, which is currently legal. Of concern is atrazine’s accumulation in certain watersheds, which can and does exceed established safety limits. To reiterate, atrazine has been studied by the EPA and has not been shown to be dangerous in low concentrations, like in the low 1 digit parts per billion. However, it is concerning that as a pollutant, it has become more concentrated in some bodies of water. Atrazine doesn’t deserve the hate it gets, but that also doesn’t mean it is perfectly safe. For more current information, such as the concentration at which aquatic plants are impacted (as of March 2025, it is 9.7 micrograms per liter), visit the EPA’s page on atrazine at https://www.epa.gov/ingredients-used-pesticide-products/atrazine.

Rapamycin

Rapamycin is an unusual immunosuppressant discovered on Easter Island (Rapa Nui), quite different from the other molecules discussed here in terms of structure, uses, and how it relates to the environment. Rapamycin was extracted from Streptomyces hygroscopicus on Easter Island in 1972. Since then, this drug has gone from being a believed antifungal agent to now being recognized as a life-saving immunosuppressant among other effects. Rapamycin inhibits mTOR (mammalian target of rapamycin) which doesn’t initially tell us anything about its function because it is part of the definition. I am not a biologist so I will try to keep this explanation simple. mTOR is an enzyme which is basically responsible for regulating cell growth and proliferation. By inhibiting it, cell growth is decreased. Besides the simple use of it as an immunosuppressant for transplants, this growth regulation opens numerous possibilities. For example, diseases or conditions which cause growths, whether they be cancerous or not, including tuberous sclerosis complex and potentially even cancer can be treated with rapamycin. In fact, it may even slow aging and increase life spans. It is certain there is a lot to research currently regarding both positive and negative effects of this drug. The main reason I have selected this molecule this week is not due to its potentially miraculous effects: I have selected it due to the question of biodiversity. We know conclusively that biodiversity of flora and fauna are decreasing and that the same holds true for both the skin and gut microbiomes – see Wallen-Russell, Christopher et al (2023). If the biodiversity of bacteria is decreasing in the environment, humanity will be affected in a very interesting way: drug discovery. Drugs like rapamycin are only discovered because they are produced by some strain of bacteria in the wild: even if we can synthesize the drug, we most likely would never have discovered it on our own due to its complexity. It is easy to look at drugs discovered in the Amazon and understand that we are inhibiting the discovery of future drugs due to climate change, fires, and more. But it is also important to consider the molecules discovered in microbes – and the devastating effects of potentially decreasing bacterial biodiversity. What continues to be certain is the vast range of negative effects at all scales due to anthropogenic climate change and pollution.

Vasicine

Vasicine is an alkaloid and quinazoline derivative found mainly in Justicia adhatoda, aka Malabar nut. This plant is a flowering shrub native to Asia, mainly parts of South and Southeast Asia. Vasicine, like many other alkaloids, has been historically used in traditional medicines. Vasicine has multiple effects on the body both as a stimulant and a depressant to different organs and systems. While this may be interesting to certain people, I have picked this molecule for an entirely different reason. While researching the reduction of nitrobenzene to aniline on my quest to determine if I could synthesize deuterated benzonitrile, I discovered a paper detailing the usage of vasicine as a reducing agent. I was looking for preferably a metal-free, non-dangerous, and cost efficient reaction and I was pleasantly surprised to find this paper, Sharma, Sushila et al (2014). I was further shocked to learn that vasicine was an abundant natural product. As a supporter of green chemistry, I was pleased at how well this reaction works and how economical it is. There are many other redox agents used in green chemistry including vitamin C and other plant extracts, and it is always good to see the discovery of another. For the sake of safety and the environment, I hope that eventually the majority of redox reactions will be done using green chemistry. It is also important to remember the conclusion of the previous molecule of the week: as the climate changes, chemistry will become harder as we may lose access to useful natural products. For more information, read the study here: https://pubs.acs.org/doi/10.1021/jo5019415

Allyl Isothiocyanate

Allyl isothiocyanate, a molecule you may not have heard of, but have certainly encountered. This natural product is present in and responsible for the flavor and pungency of horseradish, wasabi, mustard, and other cruciferous vegetables. As delicious as these foods are, allyl isothiocyanate is rarely found on its own. This is quite fortunate for humans because pure allyl isothiocyanate is actually relatively toxic with an LD50 is 151 mg/kg – slightly more toxic than MDMA and sodium nitrite. In addition, allyl isothiocyanate is a lachrymatory agent, like tear gas. In addition to being used in food, its toxicity in pure form is put to use in the form of insecticides and antibiotics. Additionally, there is some research currently ongoing into possible anti-cancer and anti-tumor effects of allyl isothiocyanate. Allyl isothiocyanate cements itself as one of the most important and most global of flavor molecules. In future weeks, I will discuss other flavor molecules responsible for the taste of foods like garlic, onions, shiitake mushrooms, and the subtle flavors of cheeses, wines, and more. Interestingly, all these molecules share something in common: they contain sulfur, my favorite element.

DDT

In honor of Earth Day being this past week, I have chosen one of, if not the most, important molecules in the history of environmental chemistry and science. Dichlorodiphenyltrichloroethane, also known as DDT, is an insecticide famously or infamously known for its effects on the environment. DDT is actually a very good insecticide – in fact its discovery led to a Nobel Prize due to its use in countering malaria. Despite its hazards, it is still used by the WHO in some countries for this reason. In 1962, biologist Rachel Carson published the book that led to the creation of the EPA: Silent Spring. Carson questioned the indiscriminate usage of DDT in agriculture, discussing the effects of it on humans and birds. Famously, DDT thins the eggshells of birds, most notably bald eagles. DDT also biomagnifies through the food chain, affecting a whole host of other organisms. In addition, DDT is considered to be a carcinogen, but the reason for this is not quite fully understood. Even if DDT only impacted 1 species, the results would be detrimental to the environment. Something that I believe a lot of people still don’t understand is how linked everything is in the environment: removing or introducing a single species can be catastrophic. For those who think this doesn’t happen anymore, look no further than Idaho. Idaho has put into place laws that pay people to kill and mercilessly slaughter wolves: reducing the number from 1500 to 150. It doesn’t take a genius to figure out how much this screws up the ecosystem: too many deer, leading to fewer plants, leading to a whole cascade of catastrophe. In California, it was recently discovered that some marijuana was grown illegally with chlorfenapyr, an absolutely horrendous pesticide illegal in the US that kills nearly everything in the environment, including humans. Dozens of other pesticides were being used with no respect for human health or the environment. 63 years after Silent Spring and 55 years after the creation of the EPA, the ideas expressed regarding fully understanding and regulating molecules we put into the environment and the importance of species (whether it’s just 1 or 100), remain incredibly relevant.

Carvone

This week is unique in that there are 2 molecules, yet both are carvone. How can this be? These 2 molecules are enantiomers of each other, meaning that they are non-superimposable mirror images of each other (it is possible to see this if you rotate each molecule in opposite directions facing each other). The bottom carbon of the cyclohexene ring (the hexagon) is an asymmetric, or chiral, carbon, meaning that it is connected to four different atoms or groups of atoms. I have tried to showcase this chirality (and not the mirror-image) by just focusing on the chiral carbon. On R-carvone, the hydrogen goes back (represented in 2-D with the dashed bond) while the other carbon group comes forward (represented in 2-D with the solid, wedge bond); the inverse is true for S-carvone. These two enantiomers cannot be switched or rotated to get the other without breaking bonds. This chiral carbon is the reason they are enantiomers and is why I have chosen to focus on it. This can be easily seen below in the hypothetical compound, bromochlorofluoromethane, a molecule with just one carbon that is chiral.

I will quickly elaborate on the naming of the 2 carvones. R and S (right and left from the Latin rectus and sinister) refer to the absolute configuration, or 3-D orientation of the enantiomers. The plus and minus refer to the direction at which polarized light is rotated by each enantiomer; this is sometimes written instead with D and L (right and left from the Latin dextro and levo). This seems strange to use, but historically, it was the only way to separate/identify enantiomers. Biologists love naming amino acids and drugs with levo and dextro for some reason but we chemists dislike this for a simple reason: I can look at a molecule and tell you immediately it is R or S, but currently, we cannot look at a molecule and predict which way it will rotate light. In short, if you tell a chemist to draw (R)-carvone, they can, but they wouldn’t know if it was dextro (+) or levo (-) carvone without testing.
Despite the 3-D configuration differences, both molecules have the same physical properties, like boiling/melting points, density, solubility in water, etc. How they smell paints a different picture: both carvones are found in nature in essential oils but (S)-carvone is present in and smells like caraway, and (R)-carvone is present in and smells like spearmint. The reason for this smell difference is quite simple: humans, like all of life, are full of enantiomers, which extends to our smell receptors. Only one of these carvone enantiomers ‘fits’ in one receptor, and the other enantiomer ‘fits’ in another receptor. These 2 receptors send different signals to the brain and the brain interprets them as 2 very different smells (it’s easy to forget that senses, like smell, aren’t inherent physical properties). This chirality of the body is why the configuration, or what we call stereochemistry, is so important for molecules that go in the body, like drugs. For example methamphetamine is chiral and only one of the enantiomers is what we know as ‘meth’; the other, levomethamphetamine, is an over-the-counter nasal decongestant.

Osmium Tetroxide

Osmium tetroxide is an interesting molecule: it is colorless but it usually appears yellow from impurities, it forms crystals, it is volatile and sublimes readily at room temperature, and its bonds are mostly covalent (as opposed to osmium having a charge of 8+). Osmium tetroxide is also quite toxic because it can enter cells due to its nonpolar nature. It can cause chemical burns to the skin, eyes, and respiratory tract, stain corneas causing blindness (permanent), and chronically damages the liver and kidneys over time. If these weren’t bad enough, osmium tetroxide is very expensive and can cost hundreds of dollars per gram. Finally, potassium permanganate (which is far cheaper, safer, and easier to handle) can perform a similar reaction. Despite this all, osmium tetroxide is arguably one of the most important reagents in organic synthesis. Both osmium tetroxide and potassium permanganate react with alkenes to form an interesting cyclic intermediate; upon hydrolysis, the alkene has been converted to an alkane and the 2 adjacent carbons have a hydroxy/alcohol group attached (vicinal diol). Due to the structure of the ring intermediate, the addition is syn, meaning that both additions happen on the same face of the molecule and the bonds are pointed in the same direction (recall the stereochemistry discussion from last week). To summarize, an alkene has been converted to an alkane and now both carbons have an alcohol group pointing in the same direction (cis diol). You often still get enantiomers depending on which side of the alkene is attacked by the osmium tetroxide, however.

This reaction is quite important because of the syn addition, but it doesn’t explain why anyone would use this seemingly horrible reagent over potassium permanganate. The first topic is reactivity: potassium permanganate is a stronger oxidizer and it can over-oxidize and break apart the diol, even if the solution is cool and dilute. This can lead to impurities and lower yields for potassium permanganate. Also due to this higher reactivity, potassium permanganate can react with alkynes, unlike osmium tetroxide; sometimes, though not always, this reaction is not desired. Finally, osmium tetroxide is used in some modified oxidation reactions. I don’t want to spoil things too much for the next 2 weeks as we discuss some of these other reagents, but some molecules can regenerate the osmium tetroxide, meaning that you can use a tiny, far less expensive amount. Furthermore, with the addition of certain ligands, you can tune the reaction so just one enantiomer is produced, allowing for the stereoselective synthesis of molecules like drugs as discussed last week. It is important to remember however that potassium permanganate is still very useful; in fact, in many if not most cases, it is the better reagent. As we will see in the next 2 weeks, osmium tetroxide can really only do a few things, but it can do them at a level no other molecule can compete at.

N-Methylmorpholine N-oxide

N-methylmorpholine N-oxide, commonly known as NMO, is one example of a molecule hinted at last week. NMO is a sacrificial catalyst and reoxidant, meaning that it is responsible for catalyzing a reaction by oxidizing the actual catalyst in a reaction. Technically, because it is not regenerated in a reaction like a catalyst, sacrificial catalysts are actually just reagents, despite the name. NMO is often used (other reoxidants like potassium ferricyanide also can work) as a method of regenerating osmium tetroxide, which itself is used in special oxidation reactions as discussed last week. For example, in Upjohn dihydroxylation (named after the former Upjohn Company), NMO is used in reagent/stoichiometric quantities to help regenerate osmium tetroxide, which is used very sparingly. Through this reaction, you can get all the benefits of osmium tetroxide while only using a tiny amount of it (which is both safer and cheaper) due to NMO regenerating osmium tetroxide after it has already reacted. This reaction, just like the normal osmium tetroxide oxidation reaction, is not stereospecific, meaning that the osmium tetroxide can attack from either face of the alkene, often resulting in a mixture of enantiomers. This mixture is known as a racemic mixture. Surprisingly, forcing this reaction to be stereospecific and produce just one enantiomer – as we will see next week – makes this reaction work faster and give higher yields, which is somewhat counterintuitive. Overall, so-called sacrificial catalysts and reoxidants represent a great way of regenerating catalysts, allowing reactions to proceed smoothly with only a very tiny amount of what may be a dangerous and/or expensive catalyst.

Dihydroquinine

Dihydroquinine (DHQ), also known as hydroquinine, is a derivative of quinine with usage in asymmetric synthesis. In 2001, K. Barry Sharpless won his first of 2 Nobel Prizes in Chemistry partially for the discovery of what is now known as Sharpless asymmetric dihydroxylation. This reaction uses osmium tetroxide as an oxidizer and uses a reoxidant, commonly potassium ferricyanide or NMO (sound familiar?). However, what makes this reaction special is the usage of an asymmetric catalyst which makes the dihydroxylation enantioselective. Both of the catalysts use phthalazine as an adduct (not actually important), but use different chiral ligands to make the reaction enantioselective. One of these ligands is the molecule of the week, DHQ, while the other ligand you use for the opposite stereochemistry is the closely related dihydroquinidine, which is the enantiomer of DHQ (just change the wedge bonds to dashed bonds). With Sharpless asymmetric dihydroxylation, alkenes can be dihydroxylated selectively such that only 1 enantiomer is made. This has huge implications in cases where a molecule has to have a certain stereochemistry, like drugs. Although this reaction isn’t perfect (depending on the steric environment of the alkene and whether it is cis or trans, selectivity varies somewhat), it is a great and relatively easy way of synthesizing 1 enantiomer. In fact, Sharpless asymmetric dihydroxylation is actually faster than Upjohn dihydroxylation (non-asymmetric) as a result of what Sharpless called ligand accelerated catalysis. Additionally, the various reagents or compounds used to generate them in situ are commercially available in what is called AD-mix. For just the low, low price of $59.28, you too (provided you can actually order it) can buy 10 grams of AD-mix-alpha from Sigma-Aldrich and perform a Nobel Prize winning reaction.

Ascorbic Acid

Ascorbic acid, aka Vitamin C, aka L-ascorbic acid (unnecessary because D-ascorbic acid is actually called erythorbic acid) is an incredibly useful molecule, perhaps more so than anything seen so far. In addition to being a vitamin found in countless fruits and vegetables, an antioxidant added to foods, and a dietary supplement used to treat or prevent scurvy, ascorbic acid finds countless uses in organic chemistry, specifically pertaining to green chemistry. Vitamin C is often first encountered in the beloved iodine clock reaction, a classic science fair or chemistry magic show demonstration that first captured my heart many years ago (watch a video of this reaction if you haven’t seen it; it’s more magical than I can describe with words). This reaction showcases the redox capabilities of ascorbic acid: the iodine is reduced (gains electrons) by ascorbic acid to form colorless iodide ions. Once the ascorbic acid has become fully oxidized (loses electrons) with the help of hydrogen peroxide, the iodine will be able to freely complex with starch, leading to a very sudden color change. Ascorbic acid finds use as a reducing agent outside of science fairs though. Ascorbic acid has historically been used as a reducing agent in green chemistry (see vasicine from 7 weeks ago) with roles like reducing graphene oxide and reducing many functional groups. Ascorbic acid has also been used as a reducing agent in atom transfer radical polymerization. Furthermore, recent research has highlighted the usage of ascorbic acid as a catalyst in organic synthesis, both due to its redox capabilities as well as its stereochemistry which can help with asymmetric synthesis. It’s rare to find a molecule that is either a good agent in synthesis or useful biologically, but ascorbic acid manages to do both.

Ferrocene

Ferrocene: the first of many molecules I have been interested in writing about for a while, but have been scared away by the task of trying to represent their structures. You may have noticed that I have not posted a 3-D structure due to this compound’s unique geometry; this may happen again with other similar compounds or ionic salts, which cannot be represented as just a 3-D molecule. With these logistics out of the way, I proudly present ferrocene.
Ferrocene is the prototypical metallocene, an interesting group of molecules which are the most common of the sandwich compounds – a name which is rather appropriate. First synthesized in 1951, ferrocene led to a Nobel Prize in Chemistry in 1973 for two of the chemists involved: Ernst Otto Fischer and Geoffrey Wilkinson. What is interesting about ferrocene and led to the Nobel Prize was not any reactions or applications of ferrocene, but the unique sandwich structure. The iron(II) in the middle of the sandwich isn’t really connected to any 1 carbon atom, as evidenced by the bonds which pass directly into the center of the cyclopentadienyl rings. Although this appears, and is complicated, these compounds have the same electron configuration of the noble gas in the period (6 pi electrons per cyclopentadienyl and 6 from iron(II)), somewhat explaining the stability of ferrocene and similar metallocenes. Even more complicated is the orientation of the cyclopentadienyl rings: depending on the temperature and phase, the rings may obtain various staggered or eclipsed conformations. For more information, I recommend checking out the Dewar-Chatt-Duncanson model, but this is far outside the scope of this blog and my understanding of organometallic chemistry. To be honest, I just picked ferrocene as a molecule because it is a relatively silly molecule: the electrons seemingly disobey rules, the molecule is relatively useless besides a few niche applications, and sandwich compound is a funny name. Chemistry is full of these rather unusual, if not silly, molecules that upon inspection, push the limits of our understanding of electrons and bonding. I hope to show a few more of these molecules eventually.

Ascaridole

Ascaridole is an interesting, naturally-occurring monoterpenoid that happens to look like a face in 2-D. Ascaridole occurs in the boldo tree of Chile and epazote, an herb which grows across Latin America. Bicyclic compounds are quite common in nature (camphor, eucalyptol, pinene, etc.) but I can’t say that I have ever seen a natural bicyclic bridging peroxide. It isn’t surprising as a result of this peroxide bridge to reveal that this molecule is relatively flammable, and some sources online regard ascaridole as being quite explosive. However, this is wrong: the peroxide bond of ascaridole does violently break with heat, but the main cycloalkene structure remains intact (unlike with other organic peroxide explosives where the entire molecule breaks apart). Hence, ascaridole is not very explosive. Besides this unusual property, ascaridole has an interesting use as an anthelmintic drug, meaning that it expels parasitic worms. However, ascaridole has mainly been used historically because it is a strong irritant and a potential carcinogen. As far as pre-1970s anti-parasitic drugs go in terms of danger (I’m looking at you, melarsoprol), this isn’t actually too bad if it means treating a parasitic infestation. There are certainly better options now, but they probably won’t be as interesting-looking of a molecule.

Previous Interesting Chemistry Publications With Environmental Applications:

Harnessing Non-Thermal External Stimuli for Polymer Recycling

Glen R. Jones, Richard Whitfield, Hyun Suk Wang, Nethmi De Alwis Watuthanthrige, Maria-Nefeli Antonopoulou, Victoria Lohmann, and Athina Anastasaki
Macromolecules Article ASAP
DOI: 10.1021/acs.macromol.4c02690

Iron-Catalyzed Hydrogenation of Alkyl Formates and Carbon Dioxide

Israel T. Pulido-Díaz, Karla P. Salas-Martin, Juan C. Montaño-Pimentel, Hector García-Mayerstein, and Itzel Guerrero-Ríos
Organometallics Article ASAP
DOI: 10.1021/acs.organomet.5c00021

Solving the Conundrum of the Influence of Irradiation Power on Photothermal CO2 Hydrogenation

Horatiu Szalad, Yong Peng, Jonas Werner Gosch, Andrea Baldi, Sven H. C. Askes, Josep Albero, and Hermenegildo García
ACS Catalysis 0, 15
DOI: 10.1021/acscatal.5c00247

Structural Stability and Photoluminescence Property of Cs2UCl6 Single Crystal Derived from Spent Nuclear Fuel

Yibo Wang, Kun Yang, Feida Chen, Xianlin Qu, Yanmei He, Daniu Han, and Xiaobin Tang
Inorganic Chemistry 2025 64 (7), 3178-3187
DOI: 10.1021/acs.inorgchem.4c04076

Room-Temperature Rh(I)-Catalyzed P(III)-Directed C–H Bond Alkylation: Enhanced Reactivity through Ligand Acceleration

Jian Zhang and Jean-François Soulé
ACS Catalysis 2025 15 (4)
DOI: 10.1021/acscatal.4c05673

Ozone Reactions with Olefins and Alkynes: Kinetics, Activation Energies, and Mechanisms

Yan Wang, Eva M. Rodríguez, Daniel Rentsch, Zhimin Qiang, and Urs von Gunten
Environmental Science & Technology Article ASAP
DOI: 10.1021/acs.est.4c07119

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