Kinetics and mechanism of the hydration of the equilibrium mixture of 3-methyl-1-buten-3-ol and 3-methyl-2-buten-1-ol with isoprene in aqueous solutions of sulfuric acid

Ryabova, R. S.; Osipova, G. F.; Винник, М. И.

doi:10.1007/bf00866577

Cited by 6 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Dimethylallyl diphosphate (DMADP) is an acid‐labile compound which can be hydrolysed to 3‐methyl‐2‐buten‐1‐ol (dimethylallyl alcohol, DMAA), 2‐methyl‐3‐buten‐2‐ol (dimethylvinyl carbinol, DMVC), and isoprene via an allylic carbocation intermediate (Ryabova et al. 1992).…”

Section: Resultsmentioning

confidence: 99%

Diurnal variation of dimethylallyl diphosphate concentrations in oak (Quercus robur) leaves

Brüggemann

Schnitzler²

2002

Physiologia Plantarum

View full text Add to dashboard Cite

In the present work a rapid and sensitive non-radioactive assay for the determination of cellular dimethylallyl diphosphate (DMADP) was developed and used for the analysis of the diurnal variation of DMADP levels in oak leaves. The method is based on the acid-catalysed hydrolysis of DMADP to isoprene, which subsequently is determined by gas chromatography. Diurnal variation of cellular DMADP levels in oak leaves of young saplings was measured on 6 days in 1998 and 1999, showing a 2 to 3-fold light-dependent increase from approximately 15 pmol mg-1 DW in the night to 31-75 pmol mg-1 DW around noon. The leaf DMADP contents showed a significant positive correlation with net assimilation and isoprene emission rates, indicating that the availability of cellular DMADP might be an important regulatory factor of leaf isoprene emission.

show abstract

Section: Resultsmentioning

confidence: 99%

Diurnal variation of dimethylallyl diphosphate concentrations in oak (Quercus robur) leaves

Brüggemann

Schnitzler²

2002

Physiologia Plantarum

View full text Add to dashboard Cite

show abstract

“…Dehydration is reversible, and water molecules can add to either ion, giving 2-methyl-3-butene-2-ol (MBO) or 3-methyl-2-butene-1-ol. The equilibrium between MBO, 3-methyl-2-butene-1-ol, and protonated isoprene has been observed in 25−50 wt % sulfuric acid solutions at 25 °C. − Both protonation and dehydration are reversible and can contribute to the effective H for MBO, but they are believed to be rapid and thus do not contribute to the observed irreversible uptake of MBO. 3-methyl-2-butene-1-ol is also likely to undergo pinacol rearrangement, which would potentially lead to 3-methylbutanal.…”

Section: Discussionmentioning

confidence: 99%

The Uptake of Methyl Vinyl Ketone, Methacrolein, and 2-Methyl-3-butene-2-ol onto Sulfuric Acid Solutions

et al. 2006

View full text Add to dashboard Cite

To investigate the link between molecular structure, reactivity, and partitioning of oxygenated organic compounds in acidic aerosols, the uptake of three compounds found in the atmosphere, methyl vinyl ketone (MVK), methacrolein (MACR), and 2-methyl-3-butene-2-ol (MBO), by sulfuric acid solutions has been measured using a rotated wetted-wall reactor (RWW) coupled to a chemical ionization mass spectrometer (CIMS). MVK was found to partition reversibly into 20-75 wt % H 2 SO 4 solutions, and we report Henry's law coefficients between 20 and 7000 M atm -1 over this range. A chemical reaction for MVK was likely responsible for the uptake observed for 80-96 wt % H 2 SO 4 solutions. We derive an upper limit to the aldol self-reaction rate coefficient for MVK in 80 wt % solution of ∼3 M -1 s -1 . MACR partitioned reversibly over most of the acidity range, and in contrast to that for MVK, the Henry's law coefficient was relatively independent of H 2 SO 4 content. These differences indicate that the increase of the coefficient with acidity is likely due to the ability of the carbonyl molecule to form an enol. These results indicate that aldol condensation can be facile in concentrated sulfuric acid solutions, but it should be negligibly slow in dilute acid solutions such as tropospheric aerosols. MBO uptake could be explained by a Henry's law coefficient that decreases slightly as acid content varies from 20 to 55 wt % H 2 SO 4 ; we also measured the value in water, 70 M atm -1 at 298 K. A steady-state uptake of MBO was observed onto 40-80 wt % H 2 SO 4 solutions, a reaction product was observed, and the reaction was tentatively identified as Pinacol rearrangement. Similar rearrangements could be at the origin of some substituted oxygenated species found in atmospheric aerosols.

show abstract

Volatile organic compounds released by enzymatic reactions in raw nonpareil almond kernel

Kwak

Faranda

Henkin

et al. 2015

Eur Food Res Technol

View full text Add to dashboard Cite

Kinetics and mechanism of the hydration of the equilibrium mixture of 3-methyl-1-buten-3-ol and 3-methyl-2-buten-1-ol with isoprene in aqueous solutions of sulfuric acid

Cited by 6 publications

References 1 publication

Diurnal variation of dimethylallyl diphosphate concentrations in oak (Quercus robur) leaves

Diurnal variation of dimethylallyl diphosphate concentrations in oak (Quercus robur) leaves

The Uptake of Methyl Vinyl Ketone, Methacrolein, and 2-Methyl-3-butene-2-ol onto Sulfuric Acid Solutions

Volatile organic compounds released by enzymatic reactions in raw nonpareil almond kernel

Contact Info

Product

Resources

About