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A substitution revolution: the legacy of Friedel-Crafts reactions in electrophilic aromatic substitution

Substitution reactions are one of organic chemistry’s most powerful tools. With substitutions, chemists can swap one functional group in a molecule for another, and otherwise-common organic compounds can be transformed into tailor-made molecules that are suitable for custom uses. As such, substituted products are often used as intermediates and precursors in a wide range of important pharmaceutical, agrochemical, and industrial applications.

In this blog, we will look at the influential electrophilic aromatic substitution known as the Friedel-Crafts reaction, and the reactions that were discovered as a result of Friedel and Crafts’ pioneering work. Not only did this reaction pave the way for substitutions in general, but Friedel-Crafts substitutions still have a profound impact on modern organic chemistry and underpin a huge number of current chemical processes.

A world of substitutions

While exchanging functional groups may sound straightforward, substitutions are very sensitive to which reagents and conditions are used. They are either electrophilic...

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The long and short of it: how extreme carbon–carbon bond lengths keep surprising chemists

June 13, 2018

The carbon–carbon single bond is the most conventional connection in organic chemistry. It is formed simply by the equal sharing of two electrons from each carbon atom. However, despite this apparent simplicity, it is fair to say that the carbon–carbon single bond is the basis for some of the most complex and important structural components of life.

Carbon is the foundation for all organic molecules as it is one of the few elements that can form long chains of its own atoms. This ability, coupled with the high strength of the single carbon bond, gives rise to an array molecular forms with a variety of differing properties. In this blog post, we will look at why this bond length can vary, and how carbon–carbon bond-forming reactions have become key steps in many syntheses of organic chemicals and natural products.

C–C bond length: testing the limits  

C–C bond length can vary dramatically....

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Going retro: Supporting the 5th National Retrosynthesis Competition 2018

May 10, 2018

A skilled chef can taste a meal they’ve never had before and tell you the list of ingredients, how they were combined, and devise a method to cook it themselves. This idea of working backwards from a final product to work out how it was made can be applied to even the most complex molecules through a technique of organic chemistry called “retrosynthesis”. Talented organic chemists can look at a molecule they’ve never seen before, and through retrosynthetic methods, determine the building blocks from which the molecule is made, and formulate a possible synthesis route.

To showcase the caliber of chemists from across the UK, the Society of Chemical Industry (SCI) and the Royal Society of Chemistry (RSC) have been working in collaboration to create the National Retrosynthesis Competition, which is now in its 5th year. The competition showcases the pioneering retrosynthetic talents of young chemists from both academia and industry,...

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Photovoltaic solar cells: The future's bright

Feb. 6, 2018

In 1839, Edmond Becquerel was tinkering in his father’s lab. He had recently become interested in studying the interaction of light with various materials, and so he decided to take some platinum electrodes and place them in an acidified silver chloride solution. The young Frenchman noted that nothing much happened to this experimental set-up in the dark; however when he illuminated the solution, a combination of these materials and light caused a current to be generated within the electrodes. What Becquerel had just stumbled upon was the world’s first photovoltaic device. But what are photovoltaics, and how are they used today?

What are photovoltaics?

An explanation for how photovoltaics worked eluded scientists for many years. It wasn’t until 1905 that a young Albert Einstein proposed a radical new theory: in a paper on the ‘photoelectric effect’ he stated that light, rather than a beam, is more accurately described as discrete, quantized ‘packets’...

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Beyond the Rule of Five

Jan. 26, 2018

Article featured in The Medicine Maker, January 2018. You can find the original article here
Why we need to explore the chemical space beyond Lipinski’s rules

Two decades on from its initial publication, Lipinski’s “rule of five” is arguably one of the most influential concepts in modern drug discovery. Yet it is also one of the most controversial. Developed with the aim of prioritizing the progression of drug candidates with the most promising oral bioavailability properties, Lipinski’s rules have had a lasting effect on drug discovery strategies and the curation of compound screening libraries. They have also inspired the creation of other similar selection criteria, such as GlaxoSmithKline’s 4/400 and Pfizer’s 3/75 rules.

The origins of the rule of five lie in a study of the favorable absorption properties of orally administered drugs and clinical candidates, conducted by Chris Lipinski and colleagues at Pfizer in 1997 (1). For four...

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