Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Z. physik. Chem. called The heats of hydration and energy contents of cis- and trans-cyclohexane-1,2-dicarboxylic acids, and their primary ions, Author is Wassermann, Albert, which mentions a compound: 610-09-3, SMILESS is O=C([C@H]1[C@@H](C(O)=O)CCCC1)O, Molecular C8H12O4, Synthetic Route of C8H12O4.
The following values were obtained for the cis- and trans-cyclohexane-1,2-dicarboxylic acids and their ions, resp.: heat of combustion, kg.-cal./mole (constant temperature) 931.9, 929.5; heat of solution + first heat of ionization, -7.49, -6.48; energy content of primary anion in dilute solution, kg.-cal./mole 939.4, 936.0; mol. volume at 0° 126.5, 120.4; second heat of ionization +0.30, +0.24. The first ionization constant of the cis acid increases with rise in temperature, while that of the trans decreases. This leads to the conclusion that the trans ion is more hydrated than the cis ion, although the heat of hydration of the undissociated cis is not measurably greater than that of the trans acid.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics