Enhancement of the water solubility of aromatic molecules via the heck reaction. A comparison of ethano-ammonium, carboxylate and -phosphonate functional groups

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Abstract

The solubility of aromatic compounds in aqueous solution is difficult to predict due to the lack of systematic solubility data and the inherent difficulties associated with theoretical predictions. Synthetic methodology is introduced for incorporating an ethano-phosphonate solubilizing group into aromatics, which has been used previously to introduce ethano-carboxyl and ethano-amino groups into aromatics. The aqueous solubility of these derivatized aromatics were carefully evaluated at 25°C so that others may use this data to further develop prediction algorithms and make simple predictions regarding solubility.

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LaBrenz, S. R., Bekele, H., & Kelly, J. W. (1998). Enhancement of the water solubility of aromatic molecules via the heck reaction. A comparison of ethano-ammonium, carboxylate and -phosphonate functional groups. Tetrahedron, 54(30), 8671–8678. https://doi.org/10.1016/S0040-4020(98)00505-5

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