Fourier-transform microwave spectroscopy of an alkyl substituted Criegee intermediate anti-CH3CHOO

Nakajima, Masakazu; Yue, Qiang; Endo, Yasuki

doi:10.1016/j.jms.2014.11.004

Cited by 39 publications

(44 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As shown in previous studies of alkyl-substituted Criegee intermediates, such as CH 3 CHOO, 14,39 C 2 H 5 CHOO 25 and (CH 3 ) 2 CHCHOO 26 the syn conformers are predicted to be the preferred configurations. This major stability can be ascribed to the attractive interaction between the terminal oxygen atom and the protons of the closer carbon atom of the alkyl moiety.…”

Section: Discussionsupporting

confidence: 53%

Fourier transform microwave spectroscopy of Criegee intermediates: The conformational behaviour of butyraldehyde oxide

Cabezas

Guillemin

Endo

2019

The Journal of Chemical Physics

Self Cite

View full text Add to dashboard Cite

Four conformers of the n-propyl-substituted Criegee intermediate, CH 3 CH 2 CH 2 CHOO, named also n-butyraldehyde oxide have been observed by Fourier transform microwave spectroscopy. The transient species was produced using a pulsed electric discharge of a gas mixture of 1,1diiodobutane/O 2 diluted in Ar or Ne. The observation of only syn species is in contrast to the results of other previous studies of alkyl-substituted Criegee intermediates, in particular those for the structural isomers, isobutyraldehyde oxide ((CH 3) 2 CHCHOO) and methyl-ethyl-ketone oxide (C 2 H 5 C(CH 3)OO), for which syn and anti species have been observed coexisting in the gas phase.

show abstract

Section: Discussionsupporting

confidence: 53%

Fourier transform microwave spectroscopy of Criegee intermediates: The conformational behaviour of butyraldehyde oxide

Cabezas

Guillemin

Endo

2019

The Journal of Chemical Physics

Self Cite

View full text Add to dashboard Cite

show abstract

“…48 Nakajima and Endo detected also the microwave spectra of alkyl-substituted Criegee intermediate syn-CH 3 CHOO 27 and anti-CH 3 CHOO. 29 The observed pure rotational transitions show a small splitting corresponding to the A/E components due to the threefold methyl internal rotation (torsion). The structure and rotational parameters were evaluated, and the barrier heights, V 3 = 837.1 and 399.1 cm .…”

Section: Larger Criegee Intermediatesmentioning

confidence: 98%

“…After the discovery of this source of CH 2 OO, many researchers utilized this scheme to produce CH 2 OO and reported ultraviolet (UV) depletion, 18 UV absorption, 19,20 infrared (IR) absorption, 21 microwave, 22,23 and submillimeter-wave 24 spectra. Spectra of slightly larger Criegee intermediates such as acetaldehyde oxide (CH 3 CHOO), 15,[25][26][27][28][29][30][31][32] acetone oxide [(CH 3 ) 2 COO], 16,33 and propionaldehyde oxide (C 2 H 5 CHOO) 10 are also reported. Figure 1 shows the structures of CH 2 OO, syn-CH 3 CHOO, and anti-CH 3 CHOO.…”

Section: Spectroscopy Of Criegee Intermediatesmentioning

confidence: 99%

See 1 more Smart Citation

Perspective: Spectroscopy and kinetics of small gaseous Criegee intermediates

Lee

2015

The Journal of Chemical Physics

158

122

View full text Add to dashboard Cite

The Criegee intermediates, carbonyl oxides proposed by Criegee in 1949 as key intermediates in the ozonolysis of alkenes, play important roles in many aspects of atmospheric chemistry. Because direct detection of these gaseous intermediates was unavailable until recently, previous understanding of their reactions, derived from indirect experimental evidence, had great uncertainties. Recent laboratory detection of the simplest Criegee intermediate CH2OO and some larger members, produced from ultraviolet irradiation of corresponding diiodoalkanes in O2, with various methods such as photoionization, ultraviolet absorption, infrared absorption, and microwave spectroscopy opens a new door to improved understanding of the roles of these Criegee intermediates. Their structures and spectral parameters have been characterized; their significant zwitterionic nature is hence confirmed. CH2OO, along with other products, has also been detected directly with microwave spectroscopy in gaseous ozonolysis reactions of ethene. The detailed kinetics of the source reaction, CH2I + O2, which is critical to laboratory studies of CH2OO, are now understood satisfactorily. The kinetic investigations using direct detection identified some important atmospheric reactions, including reactions with NO2, SO2, water dimer, carboxylic acids, and carbonyl compounds. Efforts toward the characterization of larger Criegee intermediates and the investigation of related reactions are in progress. Some reactions of CH3CHOO are found to depend on conformation. This perspective examines progress toward the direct spectral characterization of Criegee intermediates and investigations of the associated reaction kinetics, and indicates some unresolved problems and prospective challenges for this exciting field of research.

show abstract

“…After this pioneering work, the same method has been applied for generation of other CIs, like CH 3 CHOO (Taatjes et al, 2013), (CH 3 ) 2 COO (Liu et al, 2014a) and methyl vinyl ketone oxide (MVKO) (Barber et al, 2018), methacrolein oxide (MACRO) (Vansco et al, 2019), etc. These CIs have been identified with various detection methods, like photoionization mass spectrometry (Taatjes et al, 2013), infrared action (Liu et al, 2014b) and absorption Lin et al, 2015) spectroscopy, UV-visible spectroscopy (Beames et al, 2013;Sheps, 2013;Liu et al, 2014a;Ting et al, 2014;Smith et al, 40 2014;Chang et al, 2016), microwave spectroscopy (McCarthy et al, 2013;Nakajima et al, 2015), etc. In addition, utilizing the direct detection of CIs, a number of kinetic investigations of CI reactions, e.g., with SO 2 (Huang et al, 2015), water vapor (Chao et al, 2015), alcohols (Chao et al, 2019), thiols (Li et al, 2019), amines (Chhantyal-Pun et al, 2019), carbonyl molecules (Taatjes et al, 2012), and organic (Welz et al, 2014) and inorganic (Foreman et al, 2016) acids, etc., have been reported (Lee, 2015;Osborn and Taatjes, 2015;Lin and Chao, 2017;Khan et al, 2018).…”

Section: Ch I → Ch I I ( R 1 )mentioning

confidence: 99%

Kinetics of dimethyl sulfide (DMS) reactions with isoprene-derived Criegee intermediates studied with direct UV absorption

Kuo¹,

Weber²,

Fittschen³

et al. 2020

Preprint

View full text Add to dashboard Cite

Abstract. Criegee intermediates (CIs) are formed in the ozonolysis of unsaturated hydrocarbons and play a role in atmospheric chemistry as a non-photolytic OH source or a strong oxidant. Using a relative rate method in an ozonolysis experiment, Newland et al. [Atmos. Chem. Phys., 15, 9521&#8211;9536, 2015] reported high reactivity of isoprene-derived Criegee intermediates towards dimethyl sulfide (DMS) relative to that towards SO2 with the ratio of the rate coefficients kDMS+CI&#8201;/&#8201;kSO2+CI&#8201;=&#8201;3.5&#8201;&#177;&#8201;1.8. Here we reinvestigated the kinetics of DMS reactions with two major Criegee intermediates formed in isoprene ozonolysis, CH2OO and methyl vinyl ketone oxide (MVKO). The individual CI was prepared following reported photolytic method with suitable (diiodo) precursors in the presence of O2. The concentration of CH2OO or MVKO was monitored directly in real time through their intense UV-visible absorption. Our results indicate the reactions of DMS with CH2OO and MVKO are both very slow; the upper limits of the rate coefficients are 4 orders of magnitude smaller than that reported by Newland et al. These results suggest that the ozonolysis experiment could be complicated such that interpretation should be careful and these CIs would not oxidize atmospheric DMS at any substantial level.

show abstract

Fourier-transform microwave spectroscopy of an alkyl substituted Criegee intermediate anti-CH3CHOO

Cited by 39 publications

References 41 publications

Fourier transform microwave spectroscopy of Criegee intermediates: The conformational behaviour of butyraldehyde oxide

Fourier transform microwave spectroscopy of Criegee intermediates: The conformational behaviour of butyraldehyde oxide

Perspective: Spectroscopy and kinetics of small gaseous Criegee intermediates

Kinetics of dimethyl sulfide (DMS) reactions with isoprene-derived Criegee intermediates studied with direct UV absorption

Contact Info

Product

Resources

About