Monitoring Suzuki Coupling Reactions with Benchtop NMR Spectroscopy

Monitoring Suzuki Coupling Reactions with Benchtop NMR Spectroscopy

The ability to monitor and follow a chemical reaction allows chemists to study and understand the underlying factors that govern the outcome of a reaction. NMR spectroscopy is well suited for this application due to the quantitative nature of the technique as well as its superior structural elucidation capabilities. With the rise of benchtop NMR spectroscopy leading to greater access to this technique, we have previously demonstrated the use of our instrument for such purposes. In this example, adapted from a J. Chem. Ed. article recently published by Thananatthanachon and Lecklider,1 the nickel catalyzed Suzuki cross-coupling reaction of 1-bromo-4-(trifluoromethyl)benzene (1) and phenylboronic acid (2) to form 4-(trifluoromethyl)biphenyl (3) was monitored by 19F NMR spectroscopy with the NMReady-60PRO instrument.

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Eat Your Heart Out Mass Spec: Measuring 10B/11B Isotopic Ratio by NMR Spectroscopy

Eat Your Heart Out Mass Spec: Measuring 10B/11B Isotopic Ratio by NMR Spectroscopy

As I’m sure the readers of this blog know, NMR spectroscopy is used widely across all branches of chemistry due to its powerful structure elucidation capabilities and the inherently quantitative nature of the technique.  Organic relies primarily on 1H/13C  experiments where as inorganic chemistry can expand to other nuclei, like 31P and 11B.  However, there are many other applications for NMR other than just structural elucidation.  Perhaps a lesser known application of NMR spectroscopy, is its ability to determine the isotopic ratio of elements! In this blog post I would like to demonstrate a novel method to determine the 10B/11B isotopic ratio using our NMReady-60e and 1H NMR spectra! 

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Nucleophilic Substitution Reactions and Benchtop NMR

Nucleophilic Substitution Reactions and Benchtop NMR

Nucleophilic substitution reactions are frequently performed as an experiment in undergraduate organic chemistry courses. Reactions taking place at saturated carbons are mainly classified as SN1 or SN2, where S stands for substitution, N for nucleophilic, and the number indicates the molecularity of the reaction (1 for a unimolecular process, 2 for a bimolecular process). In the SN2 reaction the attack of the nucleophile and elimination of the leaving group occur simultaneously in a concerted process and its rate is proportional to the concentration of both the alkyl halide and the nucleophile.

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To apodize or not to apodize - the age old question

To apodize or not to apodize - the age old question

Are you familiar with the Apodization tool in Mnova? Apodization (also referred to as Weighting or Windowing) literally translates to ‘cutting off the feet’ from the original Greek. In this case, the ‘feet’ are the leakage or wiggles that appears when the NMR signal rapidly decays to zero. As such, apodization can enhance the resolution or the sensitivity (S/N ratio) in the spectrum and even remove truncation artefacts after data has been collected. This function is particularly useful for spectra acquired on a benchtop NMR instrument due to the lower S/N ratio compared to spectra collected on high-field instruments.

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Small Molecule Drug Discovery: From countertop to over-the-counter

Small Molecule Drug Discovery: From countertop to over-the-counter

Drug discovery is a multi-billion dollar industry and chemists play an integral role in many points on the drug discovery roadmap.  To ensure the best possible drug candidate can be produced in the fastest, most efficient and economically friendly fashion, chemists perform innovative research from early-state development through the scaling-up process.  Many analytical techniques including Nuclear Magnetic Resonance (NMR) spectroscopy are crucial in the drug discovery process and chemists use these tools daily to characterize reaction products every step of the way.  Once a chemist’s reaction is complete and the desired product isolated, an NMR spectrum of the isolate is acquired.  The chemist then interprets the spectrum by assigning the peaks in the spectrum to the unique sets of protons (1H), or other atoms (13C, 31P, 19F, 11B, etc.), in their desired molecule; corroborating they have made what they sought to make when the reaction was started.

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Think INSIDE the box! Running NMR in the Glovebox

Think INSIDE the box! Running NMR in the Glovebox

There are all sorts of different research areas in chemistry. Consider my path, for example. When I was just a young undergrad trying to find my calling, I loved tackling mechanisms for organic reactions, but I also loved the “breaking all the rules” in inorganic chemistry. In trying to decide which route I wanted to take, Prof. Stephen Westcott introduced me to the best of both worlds: organo-metallic chemistry. You get all sorts of crazy colours and many of the molecules disobey the conventional rules! You need to be careful though, because many of them will react instantly with water and oxygen. And I mean instantly! For example, although an incredibly simple organometallic molecule, tert-butyllithium (t-BuLi) is incredibly dangerous since it catches fire at the slightest hint of air.

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How strong was your coffee this morning?

How strong was your coffee this morning?

Who doesn’t want to start the day with a warm cup of coffee? Coffee has a stimulating effect on humans because of its caffeine content and for that reason it has become one of the most popular drinks in the world. Some clinical studies actually suggest that small amounts of caffeine everyday might be beneficial for adults. In this blog I am going to highlight an experiment done in collaboration with the Swager group at MIT using an organometallic complex to quantify the caffeine content in regular coffee without sample preparation!

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A bright application…

A bright application…

BODIPY dyes, which are boron difluoride compounds supported by dipyrrinato ligands, have gained recognition as being one of the more versatile fluorophores due to their superior photophysical properties.[1,2] BODIPY derivatives are used as stable functional dyes in several fields such as light harvesters, laser dyes, fluorescent switches, and biomolecular labels.[3-6] They gained popularity as biological probes due to the easy modification of the ligand framework, extension of the chromophore, and substitution of the fluorine atoms.6 Figure 1 shows some commercially available BODIPY dyes used as biological probes.

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2017 Year in Review

2017 Year in Review

With great advances in areas such as metabolomics, quantitative NMR, and online analysis, 2017 was a very exciting year for NMR in general, but specifically so for Benchtop NMR! Benchtop NMR has continued to make NMR, one of the strongest characterization techniques, become a mainstream staple in teaching and research laboratories. As users realize how easy it is to incorporate the NMReady-60 spectrometers into their laboratories, they have continued to breakthrough into new and exciting applications.

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