Spectrophotometric Studies on the Interaction between Acetone and Sulfuric Acid<sup>1</sup>

Nagakura, Saburo; Minegishi, Atsuko; Stanfield, K.E.

doi:10.1021/ja01562a006

Cited by 21 publications

(11 citation statements)

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“…Some of these spectra were of considerable interest and will be the subject of a subsequent paper. The spectrum of acetone in aqueous acids is discussed by Nagakura, Minegishi and Stanfield [15], who found that in concentrated sulphuric acid condensation occurred. Dilute solutions prepared as above showed no evidence of condensation, the salient feature being a rising absorption below 230m/~.…”

Section: Possibility Of Oxidationmentioning

confidence: 99%

Unstable intermediates

Rosenbaum

Symons

1960

Molecular Physics

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Section: Possibility Of Oxidationmentioning

confidence: 99%

Unstable intermediates

Rosenbaum

Symons

1960

Molecular Physics

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“…The polyaldol condensations of phenylacetaldehyde, acetaldehyde, and acetone have been investigated . The polyaldol condensation of phenylacetaldehyde catalyzed by sulfuric acid in dioxane leads to the formation of polyphenylacetylene .…”

Section: Resultsmentioning

confidence: 99%

“…The acetone polyaldol condensation catalyzed by acidic molecular sieves at 21–115 °C gives the diacetone alcohol (acetone dimer), mesityl oxide (acetone dimer), phorone (acetone trimer), and isophorone (acetone trimer), which have absorption peaks around 200–385 nm . It has been reported that acetone reacts with sulfuric acid to give mesityl oxide ( λ max = 284 nm) and phorone ( λ max = 339 nm) . In contrast, the reaction of acetone with sulfuric acid at 25 °C for 120 h or 150 °C for 18 h formed acetone polyaldol condensation products, such as mesityl oxide, phorone, acetone tetramers, acetone pentamers, and acetone hexamers .…”

Section: Resultsmentioning

confidence: 99%

Coloring–decoloring behavior of fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid oligomer/acetone composite in methanol

Kijima

Nishida

Fukaya

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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A reddish‐brown fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid (AMPS) oligomer/acetone composite was prepared by heating the white oligomer powder with acetone at 80 °C for 3 h. The color was not observed in the corresponding non‐fluorinated AMPS oligomer/acetone composite, which was prepared under similar conditions. The coloring was probably caused by the formation of acetone polyaldol condensation products in the fluorinated oligomeric gel network cores. The colored RF‐(AMPS)n‐RF/acetone composite powders were stable and did not exhibit any color change after 2 years in natural light at room temperature. The colored composite powders dissolved in methanol to give a reddish‐brown solution at room temperature. However, the retro‐polyaldol condensation decolored the solution after 1 day at room temperature. This is the first example of the retro‐aldol polycondensation of acetone under mild conditions. The decoloration increased by between 38‐ and 70‐fold under UV irradiation, compared with that in dark conditions. The coloring–decoloring behavior was consistent and repeatable; therefore our fluorinated oligomer/acetone composites are promising candidates for new fluorinated coloring materials. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2555–2564

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“…In strong sulphuric acid these are replaced by a single peak a t about 240 mp (Table I) which may be the .rr -+ a* peak shifted to longer wavelengths by protonation (12), the blue shift of the n --t u* peak (11) caused by protonation having taken it out of the observable region of the spectrum. These spectral changes are very similar to those already observed for thioacetamide (11,13).…”

Section: Resultsmentioning

confidence: 99%

Ionization of Organic Compounds: V. Thiolactams in Sulphuric Acid

Edward¹,

Stollar²

1963

Can. J. Chem.

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The ionization in aqueous sulphuric acid of thiolactams consisting of five-, six-, and sevenmembered rings has been studied. With increasing concentration of acid the ionization ratio increases more rapidly than ho. A possible explanation involving the hydration of the thiolactam is given. Changes in the basicity of thiolactams with ring size parallel changes previously found for lactams.By analogy with the resonance structures of simple amides (I), the structure of lactams (I; X = 0 ) would be expected to be made up by a 60y0 contribution from structure Ia (X = 0 ) and 40% contribution from structure Ib (X = 0), although the relative weights of the contributions could be altered somewhat by ring strain (2). Thiolactams (I; X = S) have higher dipole moments (3), and so should be represented to a preponderant extent by the dipolar form I b (X = S). The high polarity of the thiolactams (I; X = S, n = 3 , 4 , and 5) may in part account for the fact that they are solids a t room temperature while the corresponding lactams (I; X = 0, n = 3, 4, and 5 ) are liquid, and that (as postulated later in this paper) they appear to be more extensively hydrated in a-queous solution than are the lactams.It is probable that lactams and thiolactams in strong acid are protonated on the oxygen or sulphur atom to give the conjugate acids (11; X = 0 or S) (4). Consequently i t became of interest to compare the basicities of the two classes of compounds. I t seemedpossible that in spite of the greater intrinsic basicity of oxygen as compared with sulphur (cf. OH-and SH-), the greater negative charge on the sulphur of thiolactams would cause them to be more basic than lactams. We have accordingly determined the protonation constants of the thiolactams (I; X = S, n = 3, 4, and 5) for comparison with the protonation constants reported for the lactams (I; X = 0 , n = 3, 4, and 5) (2).

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Spectrophotometric Studies on the Interaction between Acetone and Sulfuric Acid¹

Cited by 21 publications

References 0 publications

Unstable intermediates

Unstable intermediates

Coloring–decoloring behavior of fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid oligomer/acetone composite in methanol

Ionization of Organic Compounds: V. Thiolactams in Sulphuric Acid

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Spectrophotometric Studies on the Interaction between Acetone and Sulfuric Acid1

Cited by 21 publications

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Unstable intermediates

Unstable intermediates

Coloring–decoloring behavior of fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid oligomer/acetone composite in methanol

Ionization of Organic Compounds: V. Thiolactams in Sulphuric Acid

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Spectrophotometric Studies on the Interaction between Acetone and Sulfuric Acid¹