Electrophilic Displacement Reactions. XI. Solvent Isotope Effects in the Protodeboronation of Areneboronic Acids

Journal Article · Fri May 05 04:00:00 EDT 1961 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja01470a029· OSTI ID:4029997

Kuivila, Henry G.; Nahabedian, K. V.

The effect of solvent hydrogen isotope composition (hydrogen and deuterium) on the rates of protodeboronation of p-methoxybenzeneboronic acid in 6.3 M sulfuric acid and of 2,6-dimethoxybenzeneboronic acid in 0.1 M perchloric acid were studied. In the former case k/sub H//k/sub D/ is 3.7 and the rate constant vaniation with solvent isotope composition is nearly linear. In the latter case k/sub H//k/sub D/ is 1.7 and variation of rate constant with solvent isotope composition is non-linear. This rate behavior is in quantitative accord with that expected for a rate-determining proton transfer. (auth)

• Research Organization: Univ. of New Hampshire, Durham
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-018048
• OSTI ID: 4029997
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 9 Vol. 83; ISSN 0002-7863
• Publisher: American Chemical Society (ACS)
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ARYL RADICALS
BENZENE
BORON COMPOUNDS
BORONIC ACIDS
CHEMISTRY
DEUTERIUM
HYDROGEN
ISOTOPE EFFECTS
METHOXY RADICALS
ORGANIC ACIDS
PERCHLORIC ACID
SOLVENTS
SULFURIC ACID