Comparison of Thiol and Selenol Esters With Oxy Esters in Spectroscopic Properties

Kingsbury, Charles A.; Ebert, Greg W.

doi:10.1080/03086648108078256

Cited by 6 publications

(3 citation statements)

References 25 publications

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“…Starting Materials: 4-Methylthiobenzoic Acid S -(4-Chlorophenyl) Ester, 1. p -Chlorothiophenol (50 mmol, 7.23 g) and p- toluoyl chloride (50 mmol, 7.73 g) were added to 115 mL of THF and cooled in an ice bath. To this solution triethylamine (100 mmol, 10.12 g) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

“…All cross-coupling reactions were performed under an atmosphere of dry N2 or Ar. THF was dried over 4 Å molecular sieves and titrated for water level with a 18 p-Chlorothiophenol (50 mmol, 7.23 g) and p-toluoyl chloride (50 mmol, 7.73 g) were added to 115 mL of THF and cooled in an ice bath. To this solution triethylamine (100 mmol, 10.12 g) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

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Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents

Fausett

Liebeskind

2005

J. Org. Chem.

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Thiol esters and organoindium reagents undergo palladium-catalyzed cross-coupling under mild conditions to give ketones in moderate to excellent yields. Aryl and primary/secondary alkyl organoindium reagents can be used as coupling partners. This method has two advantages over the cross-coupling of thiol esters with boron and tin reagents: (1) no added copper reagent is required to mediate the reaction and (2) for the case of alkyl transfer, no added base is required to activate organoindium reagents for cross-coupling as is required for the coupling of alkyl boron reagents with thiol esters.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents

Fausett

Liebeskind

2005

J. Org. Chem.

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“…Table 3 contains some selected data obtained by theoretical calculations and in Table 2 are compiled some spectral values collected from literature of IR and NMR spectrum in order to establish a comparative analysis. 21 The O=C-Y and Y-C sp2 bond distances of the chalcogeno esters O, S, Se and Te increase as the atomic radius increases in the order Te > Se > S > O. The calculated dipole moments also follow the same tendency in spite of the decreasing eletronegativity (in brackets) down the groups in the periodic table: O (3.44) > S (2.58) > Se (2.55) > Te (2.10).…”

Section: Resultsmentioning

confidence: 99%

An evaluation of the chalcogen atom effect on the mesomorphic and electronic properties in a new homologous series of chalcogeno esters

Rampon¹,

Rodembusch²,

Gonçalves³

et al. 2010

J. Braz. Chem. Soc.

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Uma série de calcogeno ésteres, 1a, 6a e 6b foi obtida em uma rota sintética conveniente. A análise de microscopia óptica de luz polarizada (POM) e calorimetria diferencial de varredura (DSC) mostrou que estes calcogeno ésteres apresentam uma ampla faixa de mesofase nemática. Além disso, espectros de absorção na região do UV-Vis em solução (ca.10 -5 mol L -1 ) também foram obtidos de maneira a se obter a diferença de energia entre os orbitais moleculares HOMO-LUMO, para posterior comparação com os resultados teóricos. Os valores calculados para o gap de HOMO-LUMO estão de acordo com os valores experimentais obtidos, onde a eletronegatividade do heteroátomo (O, S e Se) deve ser o principal fator para a localização do máximo de absorção. Um estudo teórico foi realizado utilizando cálculos de DFT/B3LYP com método híbrido de Becke aplicando uma correlação funcional de Lee-Yang-Parr (B3LYP) com a base DGDZVP a fim de avaliar algumas propriedades físico-químicas relacionadas com o mesomorfismo e as propriedades eletrônicas espectrais. Através da síntese destes compostos, a influência do átomo de calcogênio nas propriedades fotofísicas e mesomórficas pôde ser avaliada de uma forma mais precisa.A series of chalcogeno esters 1a, 6a and 6b have been synthesized in a straightforward manner. Polarized-light optical microscopy (POM) and differential scanning calorimetry (DSC) showed that these chalcogeno esters displayed a wide nematic range of mesophase. In addition, UV-Vis in solution (ca.10 -5 mol L -1 ) was applied in order to obtain the HOMO-LUMO gap for further comparison with the theoretical results. The calculated values to the HOMO-LUMO gap are in excellent agreement with the experimental results, where the electronegativity of the heteroatom (O, S and Se) seems to play a fundamental role in the absorption maxima location. A theoretical study was performed using a DFT/B3LYP calculations with Becke's three-parameter hybrid method applying the Lee-Yang-Parr functional correlation (B3LYP) with DGDZVP basis set in order to evaluate some physical chemistry data related with mesomorphic and spectral eletronic properties. By synthesizing these compounds we were able to get a more precise description about the influence of the chalcogen atom on the mesomorphic and photophysical properties. Rampon et al. 2101 Vol. 21, No. 11, 2010 The biological and medicinal properties of selenium and organoselenium compounds are increasingly appreciated, mainly due to their antioxidant, antitumor, antimicrobial and antiviral properties. 4 Besides, the synthesis of peptides containing selenocysteine is rapidly gaining interest with the discovery of an increasing number of proteins containing this aminoacid. Keywords 5Chalcogeno esters (thiol, selenol and tellurol esters) are useful synthetic intermediates that have been employed, for example, as acylating reagents, building blocks for heterocyclic compounds, precursors of acyl radicals and anions, as well asymmetric aldol reactions. However, rare are the examples where these compounds a...

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Oxidation of 1‐[(aryl)(phenylseleno)methyl]‐, 1‐[(aryl)(arylthio)‐(phenylseleno)methyl]‐, and l‐[(aryl)(diphenylseleno)methyl]benzotriazoles with m‐chloroperbenzoic acid

Kang

Kim

1997

Journal of Heterocyclic Chem

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During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1‐(phenylthiomethyl)benzotriazole (2a) and 1‐(2‐phenyl‐1‐phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with wj‐chloroperbenzoic acid (m‐CPBA) and sodium periodate, respectively. No compounds derived from a heterolytic cleavage between the α‐carbon and the N‐1 atoms of the foregoing compounds were isolated.

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Comparison of Thiol and Selenol Esters With Oxy Esters in Spectroscopic Properties

Cited by 6 publications

References 25 publications

Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents

Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents

An evaluation of the chalcogen atom effect on the mesomorphic and electronic properties in a new homologous series of chalcogeno esters

Oxidation of 1‐[(aryl)(phenylseleno)methyl]‐, 1‐[(aryl)(arylthio)‐(phenylseleno)methyl]‐, and l‐[(aryl)(diphenylseleno)methyl]benzotriazoles with m‐chloroperbenzoic acid

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