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The strength of a low-barrier hydrogen bond in water

✍ Scribed by Freeman M Wong; James R Keeffe; Weiming Wu

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
96 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

There are large differences between the acidity of the enol of the acyclic diketone, 2,4-pentanedione and those of two cyclic diketones, 1,3-cyclopentanedione and 1,3-cyclohexanedione. Computational studies have demonstrated that these differences are largely due to the strength of the internal low-barrier hydrogen bond (LBHB) in the enol of 2,4-pentanedione. It is thus estimated that the lower limit of the additional free energy of formation in water for this LBHB over that of a conventional hydrogen bond is 4.1-5.3 kcal mol -1 .

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