Maleic acid (
ionised maleate in biology) or (Z)-butenedioic acid or cis-butenedioic acid or malenic acid or maleinic acid or toxilic acid is an
organic compound which is a di
carboxylic acid (molecule with two
carboxyl groups). The
molecule consists of an
ethylene group flanked by two carboxylic acid groups. Maleic acid is the
cis isomer of butenedioic acid, whereas
fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in
heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 139 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the
intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions.
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