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Heterocyclic compound formation (if you like it, put a ring on it)

Aug. 29, 2018

A heterocyclic compound is a ring-structured molecule that contains at least two different elements as members of the ring. The sizes can vary, from highly strained, three-membered ring compounds, to larger molecules with eight, nine, or ten-membered ring structures. That being said, five and six-membered rings are usually the most common heterocyclic compounds, as they are less strained and thus more stable, especially in the case of aromatic heterocyclics. This structural variation in heterocycles (from ring size to the constituent elements) gives them a wide range of chemical properties and is a key reason what they have so many applications in organic chemistry.

Heterocyclic molecules make up many of the materials that are vital to life. For example, the fundamental building blocks of DNA (nucleic acids) are heterocyclic compounds, as are most naturally occurring antibiotics, vitamins, and pigments. In fact, heterocycles constitute nearly 50% of known organic compounds and almost 90%...

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Nucleophilic substitution: A powerful strategy for creating diverse chemical structures

Aug. 7, 2018

Nucleophilic substitution reactions are amongst the most widely-used transformations in organic chemistry. They facilitate the interconversion of functional groups, typically at a saturated aliphatic carbon, allowing chemists to swap specific features on one molecule for more desirable ones on another. When it comes to synthetic manipulation, there really isn’t a substitute for nucleophilic substitution!

In this blog, we consider why these reactions are so useful and take a brief look at the history of some of the most important examples.

What is nucleophilic substitution?

Nucleophilic substitution reactions involve the interaction of an electron rich nucleophile (Nuc) with the positive or partially positive charge of one or more atoms on a substrate (R-LG). The neutral or negatively charged nucleophile forms a new bond with the substrate, replacing the neutral or positively charged leaving group (LG). The most general form of the reaction is as follows:

Nuc + R-LG → R-Nuc + LG

Some of...

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

July 11, 2018

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 8, 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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