Combining in situ FTIR spectroscopy, BTEM analysis, bulk density measurements and DFT for two Diels–Alder reactions. A general approach for partial molar volume and reaction volume analyses

Tjahjono, A. Martin; Gao, Feng; Hermanto, Martin Wijaya; Cechao, Foo; Garland, Marc

doi:10.1039/c3ra47057a

Cited by 7 publications

(3 citation statements)

References 25 publications

(31 reference statements)

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“…The characteristic absorption bands in the FTIR spectrum of DCPDME isomer 3 are listed in parentheses along with the corresponding bond vibrations. The fingerprint region from 1000 to 1800 cm −1 shows absorption bands at 1073 (C-C stretching), 1098 (C-H bending), 1158 (CH 2 twisting), 1269 (C-C stretching), 1358 (C-H bending) and at 1441 cm −1 (CH 2 scissoring) [39,40]. The absorption bands near 1600 cm −1 correspond to the C=C stretching vibration, while the bands between 2800 and 3100 cm −1 correspond to the C-H stretching vibration [39,40].…”

Section: Resultsmentioning

confidence: 99%

“…The fingerprint region from 1000 to 1800 cm −1 shows absorption bands at 1073 (C-C stretching), 1098 (C-H bending), 1158 (CH 2 twisting), 1269 (C-C stretching), 1358 (C-H bending) and at 1441 cm −1 (CH 2 scissoring) [39,40]. The absorption bands near 1600 cm −1 correspond to the C=C stretching vibration, while the bands between 2800 and 3100 cm −1 correspond to the C-H stretching vibration [39,40]. This is the assignment of the main bands in the FTIR spectrum of DCPDME, while the structural differences between the individual DCPDME isomers are too small to be determined with FTIR.…”

Section: Resultsmentioning

confidence: 99%

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Dynamic Properties of Di(cyclopentadienecarboxylic Acid) Dimethyl Esters

Anžlovar,

Pavlica,

Pahovnik

et al. 2023

IJMS

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Di(cyclopentadienecarboxylic acid) dimethyl ester (DCPDME) is a potential dynamic covalent system. When such molecules are used as dynamic crosslinkers in polymers, understanding the reversibility of cyclopentadiene dimerization is crucial to determine optimal melt processing conditions. To this end, we synthesized DCPDME, which consists of three regioisomers with different physicochemical properties, which were investigated by isolating them and further characterizing them using 1H NMR, FTIR and DSC. There have been many attempts to improve the synthesis process to increase the reaction yield and purity of isomer 3, and this goal remains a challenge today. In this work, we show that pure isomers 1 and 2 irreversibly convert to the more stable DCPDME isomer 3 at temperatures between 120 and 140 °C in N2. This shows that isolation of the pure isomer 3 from the DCPDME isomer mixture is not necessary. The DCPDME isomer 3 is reversibly cleaved to the monomeric cyclopentadienecarboxylic acid methyl ester (CPME), as confirmed with GC–MS and the resulting mass spectrum. The conversion of DCPDME isomers 1 and 2 to isomer 3 was confirmed by heating the synthesized mixture of DCPDME isomers at 135 °C for 5 min in N2, producing an almost pure isomer 3 which increased its synthesis yield by 35%.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Dynamic Properties of Di(cyclopentadienecarboxylic Acid) Dimethyl Esters

Anžlovar,

Pavlica,

Pahovnik

et al. 2023

IJMS

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show abstract

“…环戊二烯及其衍生物可以进行聚合 [1] 、氢化还原 [2] 、氧化 [3] 、加成 [4,5] 和扩环 [6] 等反应, 在茂化合物、树脂、农药、橡胶、阻燃剂、医药和光电器件领域等领域已得到广泛应用 [7～9] . 溶剂中, 80 ℃和钯催化条件下将 4-羟基取代的香豆素和二苯乙炔环化生成得到化合物 1 (Eq.…”

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Research Progress on the Synthesis and Application of Cyclopentadiene Derivatives

Ye¹,

Huang²,

Wang³

et al. 2016

Chin. J. Org. Chem.

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Cyclopentadiene and its derivatives are a type of important small molecule cyclic olefin compounds, which have been widely applied in many fields such as synthesis of metallocene compounds, synthesis of organic intermediates and organic photoelectric materials. Based on our recent research results, in this review, the research progress on the synthesis of cyclopentadiene derivatives and the application of some typical cyclopentadiene derivatives in the field of organic synthesis are summarized.

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A new extension of the polarizable continuum model: Toward a quantum chemical description of chemical reactions at extreme high pressure

Cammi

2015

J Comput Chem

123

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A quantum chemical method for studying potential energy surfaces of reactive molecular systems at extreme high pressures is presented. The method is an extension of the standard Polarizable Continuum Model that is usually used for Quantum Chemical study of chemical reactions at a standard condition of pressure. The physical basis of the method and the corresponding computational protocol are described in necessary detail, and an application of the method to the dimerization of cyclopentadiene (up to 20 GPa) is reported.

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Combining in situ FTIR spectroscopy, BTEM analysis, bulk density measurements and DFT for two Diels–Alder reactions. A general approach for partial molar volume and reaction volume analyses

Cited by 7 publications

References 25 publications

Dynamic Properties of Di(cyclopentadienecarboxylic Acid) Dimethyl Esters

Dynamic Properties of Di(cyclopentadienecarboxylic Acid) Dimethyl Esters

Research Progress on the Synthesis and Application of Cyclopentadiene Derivatives

A new extension of the polarizable continuum model: Toward a quantum chemical description of chemical reactions at extreme high pressure

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