Recently, I have attended Dr. Michael Huggins’ from West Florida presentation on Hydrogen Bonding Studies with Simple Pyrrole Derivates. His studies were very complex at an advance level that was hard to comprehend completely. However, I was glad that he is an organic chemist, so some vocabulary were familiar.
He was very interested in the reaction of Dipyrrinone structure because of its rich environment for hydrogen bonding. It has hydrogen-bond pocket that could establish this possibility. The structure is a polar functional group and non-polar ends. It loves to self-associate. Many of Dr. Huggins’ experiments resulted in a failure. He presented many data on different synthesis that his students have worked on.
There was a new synthesis of Dipyrrinone, which incorporated amide. This attempt failed because it could not bond to another compound even when tried with heat. He stated that there was a revised synthesis and it did work, but he didn’t specify it clearly enough for me to gather the data from him.
He mentioned that sulfonamides were created from Sodium metal in ice bath, which created the product pyrrolon. There were other methods that he used including sulfuric acid and water by adding RNH2/Et3N together and get the final sulfamides. I was confused with this compound because he assumed that everyone in the room knew about the compound, so he did not explain any properties or how it created sulfamides.
It was interesting to see how he used a wide variety of methods and compounds to test for the hypothesized product, but many tries failed. Dr. Huggins said he will continue to come up with more different ideas that could work with hydrogen bonding in sulfamides and used Dipyrrinones to create larger structures with a linker in the future.