Computational prediction of structure and catalytic activity of new organic superacids
Principal investigator
This project aims at computational design of extremely acidic organic molecules called superacids. Based on a simple strategy of finding a suitable, well-known and available molecular skeleton subsequently polysubstituted by electron-withdrawing cyano groups, it is expected that a whole catalog of new superacids will be obtained. The latter will be compared to traditional inorganic mineral acids, like sulfuric and triflic acid, on the basis of their intrinsic and solution-phase acidities as well as in their catalytic activity. It is anticipated that the predicted compounds should exceed the acidity of sulfuric acids by more than 50 orders of magnitude, which is remarkable indeed. On the other hand, a significant improvement in catalytic activity is also foreseen. This is of particular importance, since mineral acids are still the most used catalysts in a large variety of chemical and industrial reactions, although their application is associated with a number of drawbacks and environmentally intolerable solutions. Having in mind that in general acid-catalysis stronger acids make better and more efficient catalysts, it is easy to assume that the molecules studied here would resolve a lot of experimental problems brought up by the usage of mineral acids. Therefore, driven by practical demands and fundamental challenges the objectives of this project are well justified. Once available, the proposed molecules would improve existing chemical processes and would make possible some new chemical transformation. This achievement would be of paramount importance to Croatian chemistry and chemical industry in general as it would enable them to access new markets by introducing modern, fast, cheap and environment-friendly technologies. Application of proposed molecules would facilitate that by reducing waste production, decreasing process time and additional work-up costs, increasing process yields and making chemistry safer and more economical. The primary outcomes of this fundamental research will be scientific papers published in high-quality peer-reviewed international journals of high impact-factor. This would propel overall competitiveness of main applicant in the field of computational physical-organic chemistry. Since our strategy in designing exceptionally acidic molecules involves polycyanation of organic compounds, it has to be strongly emphasized that the synthetic pathways of polycyanation are well-known and well-documented in the literature. It is, therefore, very likely that some of the suggested molecules could be prepared in the laboratory and their synthesis is highly recommended.