When two compounds whose molecules form hydrogen bonds with each other
are both dissolved in water, the hydrogen bond between the two molecules is usually
greatly weakened or completely removed,19 because the molecules generally
form hydrogen bonds with the water molecules rather than with each other, especially
since the water molecules are present in such great numbers. In amides, the
oxygen atom is the preferred site of protonation or complexation with water.20 In
the case of dicarboxylic acids, arguments have been presented that there is little or
no evidence for strong hydrogen bonding in aqueous solution,21 although recent
studies concluded that strong, intramolecular hydrogen bonding can exist in aqueous
acetone solutions (0.31 mole-fraction water) of hydrogen maleate and hydrogen
cis-cyclohexane-1,2-dicarboxylate.22
When two compounds whose molecules form hydrogen bonds with each other
are both dissolved in water, the hydrogen bond between the two molecules is usually
greatly weakened or completely removed,19 because the molecules generally
form hydrogen bonds with the water molecules rather than with each other, especially
since the water molecules are present in such great numbers. In amides, the
oxygen atom is the preferred site of protonation or complexation with water.20 In
the case of dicarboxylic acids, arguments have been presented that there is little or
no evidence for strong hydrogen bonding in aqueous solution,21 although recent
studies concluded that strong, intramolecular hydrogen bonding can exist in aqueous
acetone solutions (0.31 mole-fraction water) of hydrogen maleate and hydrogen
cis-cyclohexane-1,2-dicarboxylate.22
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