Protic and Nonprotic Ionic Liquids in Polar Diels-Alder Reactions Using Properly Substituted Heterocycles and Carbocycles as Dienophiles. A DFT study

Mancini, Paolo; Ormachea, Carla; Rosa, Claudia Della; Kneeteman, Marı́a N.; Domingo, Luís R.

doi:10.5772/51656

Cited by 3 publications

(4 citation statements)

References 30 publications

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“…Besides that, over the past few years, PILs have attracted greater attention from researchers and quite a few works have been done to reveal several potential applications using PILs. Since PILs can be synthesized by the transfer of protons from Brønsted acids to Brønsted bases, PILs can be useful solvents for acid catalyzed reactions such as Diels-Alder reaction [11][12][13]. Besides that, the presence of active protons in PILs will allow PILs to be suitable electrolytes in fuel cells [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Thermophysical Properties of Newly Synthesized Ammonium-Based Protic Ionic Liquids: Effect of Temperature, Anion and Alkyl Chain Length

et al. 2020

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Ionic liquids which are often classified as low melting point salts have received significant attention from research groups and industries to be used in a wide range of applications. Many of these applications require thorough knowledge on the thermophysical properties of the ionic liquids before utilizing their full potentials in various fields. In this work, a series of alkylammonium cation and carboxylate anion-based room temperature protic ionic liquids (PILs) were synthesized by varying length of alkyl chain of the cation from diethyl to dibutyl combined with pentanoate, hexanoate and heptanoate anions. These ammonium-based PILs named as diethylammonium pentanoate [DEA][C5], diethylammonium hexanoate [DEA][C6], diethylammonium heptanoate [DEA][C7], dibutylammonium pentanoate [DBA][C5], dibutylammonium hexanoate [DBA][C6] and dibutylammonium heptanoate [DBA][C7] were characterized using Nuclear Magnetic Resonance (NMR) spectroscopy. The thermophysical properties of the PILs namely density, dynamic viscosity and refractive index were measured and analyzed. Density, ρ and dynamic viscosity, η were determined at T = (293.15 to 363.15) K and refractive index, nD was measured at T = (293.15 to 333.15) K. The fitting parameters are proposed for the empirical correlations of density, dynamic viscosity and refractive index. The values of thermal expansion coefficient, αp, molecular volume, Vm, standard entropy, S° and lattice potential energy, Upot also have been calculated by using the specified equations. The thermal decomposition temperature, Td was also determined using a thermogravimetric analyzer (TGA) while the differential scanning calorimetry (DSC) technique provided the glass transition, Tg, melting point, Tm and crystallization, Tc temperatures of the PILs. The experimental results revealed that the dependency of the experimental values namely the ρ, η, nD, and Td on the alkyl chain of the anion, size of the cations and the temperature of measurement.

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Section: Introductionmentioning

confidence: 99%

Thermophysical Properties of Newly Synthesized Ammonium-Based Protic Ionic Liquids: Effect of Temperature, Anion and Alkyl Chain Length

et al. 2020

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“…When the 1a y 1b reacted with 4 under the same conditions, afforded the indole 5c ( Table 1, entries [5][6][7][8], the best results were obtained with free-solvent experience showing high yields.…”

Section: Figurementioning

confidence: 99%

“…These dienophiles reacted with dienes strongly, moderately and poorly activated reactions for obtain in one step the respective cicloadducts. [4][5][6][7][8] Considering that microwave irradiation (MW) have been used to enhance organic reactions we have realized some experiences with some of these polar process using this methodology. Then, and taken into account the results obtained with the polar Diels-Alder (P-DA) reactions developed in normal thermal conditions, the principal aim of this work is to study the influence of microwave irradiation in the cycloaddition reactions of pyrroles and indoles nitro-substituted, exposed to dienes of different nucleophilicity in the presence of benzene as solvent and complementary in free-solvent conditions.…”

Section: Introductionmentioning

confidence: 99%

Microwave Irradiation: Polar Diels-Alder Reactions Using Nitropyrrole and Nitroindole Derivates as Electrophiles

Mancini

Kneeteman

Baena

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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In this work we studied the influence of the microwave irradiation in polar Diels-Alder reactions using nitropyrrole and nitroindole derivatives as electrophiles with dienes of different nucleophilicity. The cycloadditions was performed under two conditions with benzene as the reaction medium and solvent free. The results clearly confirm that the use of microwave irradiation in this type of reactions have advantages in relation to the carried out under classical heating. In general the products obtained are similar, but reaction times are lower and the yields increases.

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“…As a consequence, the characterization of the properties of different classes of ILs used as solvents for specific applications and for chemical reactions and catalysis have been intensively investigated. 11 Due to their ionic nature, the structure of ILs is able to incorporate different levels of complexity. First, and in order to maintain local electroneutrality, the high-charge density parts of cations and anions must create a three-dimensional network where the nearest neighbours of a given ion are of the opposite sign.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies on polar Diels–Alder reactions of 1-nitronaphathalene developed in ionic liquids

et al. 2013

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Protic and Nonprotic Ionic Liquids in Polar Diels-Alder Reactions Using Properly Substituted Heterocycles and Carbocycles as Dienophiles. A DFT study

Cited by 3 publications

References 30 publications

Thermophysical Properties of Newly Synthesized Ammonium-Based Protic Ionic Liquids: Effect of Temperature, Anion and Alkyl Chain Length

Thermophysical Properties of Newly Synthesized Ammonium-Based Protic Ionic Liquids: Effect of Temperature, Anion and Alkyl Chain Length

Microwave Irradiation: Polar Diels-Alder Reactions Using Nitropyrrole and Nitroindole Derivates as Electrophiles

Experimental and theoretical studies on polar Diels–Alder reactions of 1-nitronaphathalene developed in ionic liquids

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