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Pseudoacids. I. 4- and 5-oxoacids

E J Valente1, J F Fuller, J D Ball

  • 1Department of Chemistry, Mississippi College, Clinton 39058, USA. valente@mc.edu

Acta Crystallographica. Section B, Structural Science
|May 15, 1998
PubMed
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Certain oxoacids cyclize into lactol forms, existing in solid states and chloroform solutions. These cyclic structures exhibit distinct bond lengths and hydrogen-bonding patterns, influencing their solid-state and solution behavior.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Physical Chemistry

Background:

  • Oxoacids with proximate carboxylic acid and carbonyl groups can form cyclic lactol (pseudoacid) structures.
  • These cyclic forms are relevant for understanding the chemical behavior and structural diversity of organic acids.

Purpose of the Study:

  • To investigate the crystal structures of various oxoacids that can exist in cyclic lactol forms.
  • To analyze the structural characteristics and hydrogen-bonding patterns of these cyclic compounds in both solid and solution states.

Main Methods:

  • X-ray crystallography was employed to determine the solid-state structures of several oxoacids, including trans-4-methyl-3-oxo-6-hydroxytetrahydropyran-3-carboxylic acid, penicillic acid, mucochloric acid, 2-methanoylbenzoic acid, 2-ethanoylbenzoic acid, 2-(2'-oxoethyl)benzoic acid, and 5-oxopentanoic acid.

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  • Solution behavior was studied using NMR spectroscopy, and structural analysis included bond length measurements and hydrogen bonding characterization.

    • Main Results:

    • Crystal structures confirmed the cyclic lactol forms for several oxoacids, including a trimeric cyclic trioxane for 5-oxopentanoic acid.
    • In solution, mixtures of open-chain and cyclic forms were observed.
    • Analysis revealed lengthened endocyclic lactol C-O bonds (1.46-1.48 Å) and shortened exocyclic C-O(H) bonds (1.38 Å) in furanoid and pyranoid pseudoacids. Distinct hydrogen-bonded dimers were observed for 3-hydroxy-3,4-dihydroisobenzopyran-1-one.

    Conclusions:

    • The study confirms the existence and structural details of cyclic lactol forms of oxoacids in both solid and solution states.
    • Specific hydrogen-bonding motifs, such as chains and dimers, are characteristic of these cyclic structures and influence their properties.