Molecule of the Week Updates

Editor’s note: Molecule of the Week has been around for more than 20 years, and new information about previous MOTWs increasingly appears in the chemical literature. This week, we catch up on four former MOTWs.

Benzoic acid¹ (Figure 1) was the Molecule of the Week for December 21, 2020. The simplest aromatic carboxylic acid, it is a commonly used preservative in foods and a snowflake mimic in holiday snow globes.

This past August, Yifan Meng, Richard N. Zare*, and Elumalai Gnanamani* at Stanford University (CA) and the Indian Institute of Technology Roorkee reported a catalyst-free method for producing phenol from benzoic acid. They electrosprayed ≈10-μm microdroplets of the acid dissolved in water into a chamber (e.g., a mass spectrometer port) to realize a calculated yield of ≈4.7%. The method has yet to be scaled up.

Formamide² (Figure 2) was the Molecule of the Week for June 22, 2015. The simplest carboxylic acid amide, it is made commercially via the reaction of methyl formate with ammonia. It is found widely in outer space.

In August, Tuğçe Beyazay, William F. Martin, and Harun Tüysüz* at the Max Planck Institute for Coal Research (Mülheim an der Ruhr) and the University of Düsseldorf (both in Germany) described a simple way to synthesize formamide. Under mild, hydrothermal conditions, they passed carbon dioxide and water over Ni–Fe nitride heterostructures, which act as both a catalyst and a nitrogen source. No yield data were reported, but the authors stated that under optimized conditions, significant quantities of formamide and formic acid were produced.

Cannabidiol³ (CBD, Figure 3) was the Molecule of the Week for February 6, 2017. It is a non-psychoactive cannabinoid from marijuana that is used for pain relief and has been approved by the US Food and Drug Administration for treating seizures caused by epilepsy and other conditions.

Earlier this month, Antoinette S. Perry and co-workers at University College Dublin reported that cannabidiol inhibits the proliferation and invasiveness of prostate cancer cells. In an in vitro study, the researchers observed that CBD inhibited cell viability and proliferation, accompanied by reduced expression of key cell-cycle proteins and inhibition of phosphorylation of the protein kinase AKT.

Cubane⁴ (Figure 4) was the Molecule of the Week for March 10, 2008. Once thought to be impossible to synthesize because of its high angle strain, the feat was finally accomplished in 1964 by Philip E. Eaton* and Thomas W. Cole, Jr, at the University of Chicago. In 2015, Ronny Priefer at Western New England University (Springfield, MA) and coauthors at other institutions wrote a 50-year review of the molecule.

Last December, Xujun Zheng, Stephen L. Craig, and colleagues at Duke University (Durham, NC) described a study of the mechanochemistry of cubane. In one example, they found that force applied to a 1,2-disubstituted cubane produced a single tricyclic cubane isomer, whereas heating the same derivative led to multiple decomposition products.⁵

1. CAS Reg. No. 65-85-0.
2. CAS Reg. No. 75-12-7.
3. CAS Reg. No. 13956-29-1.
4. CAS Reg. No. 277-10-1.
5. This update was suggested by a reader.