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Understanding “on-water” catalysis of organic reactions. Effects of H+ and Li+ ions in the aqueous phase and nonreacting competitor H-bond acceptors in the organic phase: On H2O versus on D2O for Huisgen cycloadditions
For a typical Huisgen cycloaddition, carried out on water, the behavior of water molecules at the oil-water interface depended on the properties of the reactants. With weakly basic reactants, a small quantity of added H+ (HClO4, 0.0001-0.01 M) present in the aqueous phase had negligible effects, but larger quantities of H+ (HClO4, 0.1-3.0 M) increased the catalytic effect and caused protons to cross the water-organic interface and affect the products. Added Li+ ions (LiClO4, 0.1-3.0 M) had no effect for on-water reactions but enhanced the rates and endo products for in-water reactions. For these cycloaddition reactions, the product endo:exo ratios, when compared to those in organic solvents, can be used to distinguish between the on-water and in-water modes. Comparisons of organic reactions on H2O and on D2O indicate that on-water catalysis ranges from weak to strong trans-phase H-bonding for reactants with basic pKa < ca. -6 and to interfacial proton transfer for reactants with higher basic pKa > ca. 2 (pKa of conjugate acid). Water shows a chameleon-type response to organic molecules at hydrophobic surfaces.
We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 253-52-1, and how the biochemistry of the body works.Electric Literature of 253-52-1
Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N90 – PubChem