Gas-phase reactions. 29. Thioacrolein

Bock, Hans; Mohmand, Shamsher; Hirabayashi, Toshiyuki; Semkow, Andrzej

doi:10.1021/ja00365a068

Cited by 38 publications

(10 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…These ionizations are in good agreement with those reported for thioacrolein (sulfur lone pair: 8.87 eV, antibonding and bonding orbitals of the CACOCAS system: 9.9 and 12 eV) (11). The substituent effect of the two methylene groups is more important on the symmetry orbitals (0.6 eV) than on the first ionization, corresponding to the sulfur lone pair (0.3 eV).…”

Section: Interpretation Of the Photoelectron Spectrasupporting

confidence: 89%

Gas-Phase Generation and Photoelectron Spectra of Reactive Unsubstituted Cycloalkenethiones

Chrostowska

Miqueu

Pfister‐Guillouzo

et al. 2001

Journal of Molecular Spectroscopy

View full text Add to dashboard Cite

Section: Interpretation Of the Photoelectron Spectrasupporting

confidence: 89%

Gas-Phase Generation and Photoelectron Spectra of Reactive Unsubstituted Cycloalkenethiones

Chrostowska

Miqueu

Pfister‐Guillouzo

et al. 2001

Journal of Molecular Spectroscopy

View full text Add to dashboard Cite

“…APTHS, with a 1-propenyl group at the R'-position of R-S-S(O)-R' was most unstable, with less than 40% of APTHS remaining intact at 0 o C after 24 h. The stability of APTHS can be compared with the stability of PATHS, which also has the same 2 alkenyl groups, but at interchanged positions. It has been reported that thiosulfinates with an allyl group at the R-position tend to be readily decomposed to thioacrolein and allyl mercaptan (15)(16)(17)(18), and that thiosulfinates with 1-propenyl at the R'-position are unstable (18). APTHS was the most unstable due to both of these conditions.…”

Section: Resultsmentioning

confidence: 99%

“…Despite a potent antimicrobial activity, garlic has not been used as a food preservative because of a strong odor (5-7) and instability (2,(8)(9)(10)(11)(12)(13)(14). The stability of garlic thiosulfinates is influenced by temperature (2,(8)(9)(10)(11)(12)(13), pH (11)(12)(13)(14), solvents (2,9), molecular structure (15)(16)(17)(18), and the concentration of garlic (2). In addition to known factors, garlic has been suggested to contain unknown substance(s) that induce faster decomposition of thiosulfinates (2).…”

Section: Introductionmentioning

confidence: 99%

“…The molecular stability of different thiosulfinates is different depending on alk(en)yl groups attached to the R-S-S(O)-R' backbone (2,(15)(16)(17)(18). Thiosulfinates that contain an allyl group at the R position (15)(16)(17) and thiosulfinates with a 1-propenyl group at the R' position (2) are known to be unstable.…”

Section: Introductionmentioning

confidence: 99%

“…Thiosulfinates that contain an allyl group at the R position (15)(16)(17) and thiosulfinates with a 1-propenyl group at the R' position (2) are known to be unstable. Allicin was reported to be less stable as the concentration increased (2).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Factors influencing the stability of garlic thiosulfinates

Lee

Kim²,

Kyung

2014

Food Sci Biotechnol

View full text Add to dashboard Cite

Despite a potent antimicrobial activity, garlic (Allium sativum L.) has not been used as a commercial food preservative because of instability of the antimicrobial activity, among other reasons. Factors influencing the stability of thiosulfinates in garlic were investigated to improve understanding of the antimicrobial activity of garlic in food preservation. As temperature, pH, the garlic concentration, and the liquid oil content increased, the stability of thiosulfinates decreased. Thiosulfinates were more unstable as the degree of unsaturation of fatty acids was increased. Solid fatty acid did not affect the stability of thiosulfinates. Other major food components, such as free amino acids, proteins, and carbohydrates did not influence the stability of thiosulfinates. Garlic can be used as a natural preservative for food items with low pH values and with low oil contents stored at low temperatures.

show abstract

The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Rickborn

1998

Organic Reactions

View full text Add to dashboard Cite

This review (Part II) is topically organized around the dienophile that is generated in a retro [4 + 2] reaction, and to the extent possible follows the principles adopted for Part I, which covers reactions in which both dienophile bonding centers are carbon atoms. The present chapter encompasses retro–Diels–Alder (rDA) reactions in which one or both of the dienophile reaction centers are heteroatoms. Any of the other atoms in the starting material (cycloadduct) may be carbon or heteroatom. Substituents on all positions are encompassed, and any bond order available to any oxidation state of an element is included, as is bonding to non‐nearest neighbor atoms (e.g., bicyclics). The reader is directed to Part I (Vol. 52) for general discussion of the rDA reaction, the features that affect rates and outcome, and the use of acids, bases, other catalysts, and scavengers. Certain subclassifications (e.g., processes proposed under MS conditions, polymer applications) of rDA reactions have been omitted from both sections; these topics are listed in the Introduction to Part I. Citations to over 100 reviews on various aspects of the rDA reaction are collected at the beginning of the References to Part I. Those that are especially pertinent to Part II will be repeated here, in the context of the particular dienophile under discussion. The decision to split the review of the rDA reaction into two parts was based on the volume of literature encountered, as outlined in the Introduction to Part I. Active literature searching was concluded for both Parts in April 1995, although occasional more recent references have been included.

show abstract

Gas-phase reactions. 29. Thioacrolein

Cited by 38 publications

References 0 publications

Gas-Phase Generation and Photoelectron Spectra of Reactive Unsubstituted Cycloalkenethiones

Gas-Phase Generation and Photoelectron Spectra of Reactive Unsubstituted Cycloalkenethiones

Factors influencing the stability of garlic thiosulfinates

The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Contact Info

Product

Resources

About