Buijs, W. A Molecular Modeling Study into Brønsted and Lewis Acid Catalyzed Conversion of CBD into Other Cannabinoids. Biologics2024, 4, 75-87.
Buijs, W. A Molecular Modeling Study into Brønsted and Lewis Acid Catalyzed Conversion of CBD into Other Cannabinoids. Biologics 2024, 4, 75-87.
Buijs, W. A Molecular Modeling Study into Brønsted and Lewis Acid Catalyzed Conversion of CBD into Other Cannabinoids. Biologics2024, 4, 75-87.
Buijs, W. A Molecular Modeling Study into Brønsted and Lewis Acid Catalyzed Conversion of CBD into Other Cannabinoids. Biologics 2024, 4, 75-87.
Abstract
There is a continuous interest in cannabinoids like Δ9-tetrahydro cannabinol (Δ9-THC) and cannabidiol (CBD). A patent of Webster et al., described the conversion of CBD to either D8-THC or D9-THC, depending on the acid catalyst applied. The use of para-toluene sulfonic acid (pTSA) led to the formation of D8-THC, while boron trifluoride etherate (BF3·Et2O) yielded mainly D9-THC. The enormous difference in product selectivity between these two catalysts was investigated with Molecular Modeling. It was found that pTSA leads to fast isomerization of Δ9-CBD to Δ8-CBD and subsequent ring closure to Δ8-THC. BF3·Et2O catalysis leads to the formation of tertiary carbenium ions in the Transition States which yield D9-THC and some iso D8-THC. Under dry conditions in refluxing toluene, it was found that pTSA is predominantly present as a dimer, and only a small fraction is available as monomeric catalyst. Applying the computationally derived activation barriers in Transition State theory yielded reaction rates predicting amounts of cannabinoids that are in close agreement with the experimental findings.
Keywords
cannabinoids; density functional theory; transition state theory
Subject
Biology and Life Sciences, Biochemistry and Molecular Biology
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
