72. Chemical constitution and the dissociation constants of monocarboxylic acids. Part IX. Monosubstituted β-phenylpropionic and cinnamic acids

Dippy, J. F. J.; Page, J. E.

doi:10.1039/jr9380000357

Cited by 24 publications

(15 citation statements)

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“…In actual fact, the Hammett constants, σ, have been found to correlate with p K a of phenylacetic acids (ρ = 0.489) and β-phenylpropionic acids (ρ = 0.212). Since the effects cannot be explained by resonance it is believed to be an inductive effect …”

Section: Introductionmentioning

confidence: 99%

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

2016

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It was established that para-substituted benzyl ether protecting groups affect the reactivity of glycosyl donors of the thioglycoside type with the N-iodosuccinimide/triflic acid promoter system. Having electron donating p-methoxybenzyl ether (PMB) groups increased the reactivity of the donor in comparison to having electron withdrawing p-chloro (PClB) or p-cyanobenzyl ether (PCNB) protecting groups, which decreased the reactivity of the glycosyl donor relative to the parent benzyl ether (Bn) protected glycosyl donor. These findings were used to perform the first armed-disarmed coupling between two benzylated glucosyl donors by tuning their reactivity. In addition, the present work describes a highly efficient palladium catalyzed multiple cyanation and methoxylation of p-chlorobenzyl protected thioglycosides. The results of this paper regarding both the different electron withdrawing properties of various benzyl ethers and the efficient and multiple protecting group transformations are applicable in general organic chemistry and not restricted to carbohydrate chemistry.

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Section: Introductionmentioning

confidence: 99%

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

2016

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“…(4) The proportionalities observed in sections 2 and 3 imply the more general expression188 ( 2)]2.37 (6) From the point of view of this relation the applicability of eq 5 means that +( 3) is proportional to +( 2€ ) -(XCH2COO-).19 We shall return to this in section 6a.…”

Section: Discussionmentioning

confidence: 90%

“…Where brackets and superscripts are absent, the correction is negligible. 6 "Overall'' pK* value in 50% ethanol: X = CH2, 4-NH2 5.93; X = CMe2, 4-NH2 6.37; X = NH, 3,5-Me 5.06; H 4.92; X = NHCH2, H 5.56. -"Overall" pKt, value in 75 % ethanol: X = CH2, 3-NH2 6.58,4-NH2 6.63; X = NH, 3,5-di-Me 5.57. "…”

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confidence: 99%

“…Soc., 1470(1954; 2995 (1956); 3,9 °p, reaction constant; sp, standard deviation of p; s, standard deviation of the experimental points; R, correlation coefficient; pKf, intercept of the regression line with the ordinate ( = 0); substituents, actual substituents in the compounds involved in the calculation of p, identified according to their number mentioned in the text. 6 Reference 9. c Reference 3. d Reference 4; the statistical data given there are in error. .…”

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confidence: 99%

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Substituent effects. III. Dissociation constants of .beta.-arylpropionic acids, .beta.-arylisovaleric acids, N-arylglycines, aryloxyacetic acids, N-aryl-.beta.-alanines, and some related systems

Hoefnagel¹,

Monshouwer²,

Snorn³

et al. 1973

J. Am. Chem. Soc.

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“…17 (s, 3H), 6.19 (d, J＝16.0, 1H), 7.03 (d, J＝8.0, 2H), 7.22 (d, J＝8.0 Hz, 2H), 7.55 (d, J＝16.0 Hz, 1H)[29] c 3.85 (s, 3H), 6.34 (d, J＝15.9 Hz, 1H), 6.95 (d, J＝ 8.7 Hz, 2H), 7.54 (d, J＝8.7 Hz, 2H), 7.77 (d, J＝ 15.9 Hz, 1H)[29] d 6.38 (d, J＝16.0 Hz, 1H), 7.61 (d, J＝16.0 Hz, 1H), 7.…”

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confidence: 99%

Synthesis of Poly(p-aminophenol) Microsphere-Supported Palladium Complex and Evaluation of Its Catalytic Performance for Heck Reaction

Nie¹,

Zhang²,

Cui³

2013

Chin. J. Org. Chem.

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Poly(p-aminophenol) microspheres were prepared by template polymerization of p-aminophenol in the presence of horseradish peroxidase as bio-enzyme catalyst. The average size of poly(p-aminophenol) microsphere is about 2 µm. Further, poly(p-aminophenol) microspheres as obtained were loaded with palladium to generate poly(p-aminophenol) microsphere-supported Pd complex. Resultant Pd complex catalyst supported by poly(p-aminophenol) microsphere was characterized by means of IR, XRD, XPS, SEM, TG etc. XPS confirms the presence of zerovalent palladium. Poly(p-aminophenol) microsphere maintains their configuration after coordination with palladium chloride, while a large number of fine Pd particulates are uniformly adsorbed on poly(p-aminophenol) microspheres. The complex is an efficient catalyst for Heck arylation of acrylic acid, styrene with aryl iodide under solvent-free condition and it also exhibits catalytic activity for activated bromobenzene. Yield of cinnamic acid was 92% for Heck reaction of acrylic acid with iodobenzene even though the complex was used 5 times.

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72. Chemical constitution and the dissociation constants of monocarboxylic acids. Part IX. Monosubstituted β-phenylpropionic and cinnamic acids

Cited by 24 publications

References 0 publications

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity

Substituent effects. III. Dissociation constants of .beta.-arylpropionic acids, .beta.-arylisovaleric acids, N-arylglycines, aryloxyacetic acids, N-aryl-.beta.-alanines, and some related systems

Synthesis of Poly(p-aminophenol) Microsphere-Supported Palladium Complex and Evaluation of Its Catalytic Performance for Heck Reaction

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