Abstract
We analyzed the interactions present in complexes that acetone, azomethane, dimethylamine, dimethyl ether, methyl acetate, and oxirane form with 39 different (H2O)n clusters (n = 1-10). A random generation of configurations and a subsequent screening procedure were employed to sample representative interactions. Using quantum chemical computations, we calculated the associated binding energies, which range from -0.19 to -10.76 kcal/mol at the DLPNO-CCSD(T)/CBS level. It was found that the binding energies can be understood in terms of various factors, including the water cluster size, the nature of the organic molecule, and the type of hydrogen bond donor. We find that the most stable complexes often arise from a combination of a strong hydrogen bond plus a secondary interaction between the organic molecule and the water cluster.
Highlights
IntroductionDiels and Alder mixed furan and maleic anhydride in hot water, obtaining a cycloaddition adduct with an increased endoselectivity compared to their organic solvent counterpart.[1] it was not until the 1980s that a systematic and pioneering series of papers by Breslow and coworkers established the paradigm of water as useful and relevant in organic chemistry
Water can be used as a reaction medium in organic chemistry
In the process of our study, we developed a new benchmark data set of hydrogen bonding for organic molecule-water cluster complexes
Summary
Diels and Alder mixed furan and maleic anhydride in hot water, obtaining a cycloaddition adduct with an increased endoselectivity compared to their organic solvent counterpart.[1] it was not until the 1980s that a systematic and pioneering series of papers by Breslow and coworkers established the paradigm of water as useful and relevant in organic chemistry. It was demonstrated that H2O as a solvent increases the reaction rate of Diels-Alder reactions 700-fold, compared to reactions in organic solvents, mainly due to hydrophobic effects.[2,3,4,5] Breslow’s seminal contributions set the foundations of aqueous organic chemistry (AOC) as a new field of research that is highly active today.[6,7,8] One of the key areas of activity is developing chemical procedures that reduce organic solvent usage in favour of H2O;9,10 the non-toxicity, reusability, and low-cost of water perfectly align with the principles of green chemistry.[11] It is expected that further expanding research in AOC will lead to significant discoveries in chemistry
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