Solvent–solute interactions of isomeric phthalaldehydes in aqueous solutions
| Autor: | Petr Zuman, M.S. Baymak, Eliona Kulla |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Geminal diol
Nucleophilic addition Aqueous solution Condensed Matter Physics Resonance (chemistry) Medicinal chemistry Atomic and Molecular Physics and Optics Electronic Optical and Magnetic Materials Solvent chemistry.chemical_compound chemistry Covalent bond Materials Chemistry Hemiacetal Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Spectroscopy |
| Zdroj: | Journal of Molecular Liquids. :24-28 |
| ISSN: | 0167-7322 |
| DOI: | 10.1016/j.molliq.2006.08.056 |
| Popis: | In contrast to aliphatic and π -deficient N -heterocyclic aldehydes, which readily in aqueous solutions covalently add water, the majority of benzenoid aldehydes is present in aqueous solutions at less than 3% in the hydrated geminal diol form. The only reported exception present some nitrobenzaldehydes. No information has been available on the effect of other electron-withdrawing groups on increased reactivity of the CH O group towards nucleophilic addition of water. Considerable difference between such reactivity of the three isomeric benzenedicarboxaldehydes is reported. Combination of electrochemical and spectrophotometric evidence proved that 1,3-benzenedicarboxaldehyde is less than 3% hydrated and 1,4-benzenedicarboxaldehyde is 24% present as geminal diol. Strong hydration indicates a strong resonance interaction between the two CHO groups in para position. Polarographic investigation demonstrated that in aqueous solution the 1,2-benzenedicarboxaldehyde (orthophthalaldehyde) is present in about 10% in unhydrated, about 20% in an acyclic monohydrated and in 70% in a cyclic hemiacetal form. The latter is generally assumed to be the only form present. |
| Databáze: | OpenAIRE |
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