13C and 15N NMR Characterization of Amine Reactivity and Solvent Effects in CO2 Capture

Perinu, Cristina; Arstad, Bjørnar; Bouzga, Aud M.; Jens, Klaus

doi:10.1021/jp503421x

Cited by 26 publications

(29 citation statements)

References 31 publications

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“…These values were in good agreement with those already reported in the literature, 11 such as for instance 168.5 and 160.7 ppm in Shi et al 12 Also for the amines, the chemical shift values changed as a function of the degree of protonation or rather on the amine/amineH + ratio. It has been typically observed that the nuclei (i.e., H α and C β ) located at a site separated by two covalent bonds from the site of protonation (i.e., N) showed a ppm shift larger than other nuclei.…”

Section: Chemical Reactionssupporting

confidence: 92%

“…6 Based on reactions 3−7, the species at equilibrium that we expected to observe and quantify by 13 C NMR spectroscopy after the carbamate formation reaction are reported in Figure 2. 3. EXPERIMENTAL SECTION 3.1.…”

Section: Chemical Reactionsmentioning

confidence: 99%

“…The hydroxyl function played a role in defining the basicity of the molecules, which increased with increasing distance between -OH and -NH 2 (from pK b = 4.52 of MEA to pK b = 3.56 of 5A1P), 20 and the amount of carbamate decreased as basicity increased due to the solvent effect (i.e., water) which was higher for the stronger bases. 6 The same molecules have also been analyzed by other authors, looking at the overall CO 2 absorption and desorption capacity. 5 In particular, the chain length alone made no strong impact on the CO 2 absorption and desorption, and, in our investigation, it appeared that the amines had similar features as the apparent carbamate decomposition constants were similar.…”

Section: Rnh ][Hco ] [Rnhcoo ]mentioning

confidence: 99%

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NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture

Perinu

Arstad

Bouzga

et al. 2014

Ind. Eng. Chem. Res.

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The amine carbamate related equilibrium (RNHCOO − + H 2 O ⇆ RNH 2 + HCO 3 − ) has been investigated with 13 C NMR (Nuclear Magnetic Resonance) spectroscopy for a series of linear primary alkanolamines, and the apparent carbamate decomposition equilibrium constants have been estimated. A quantitative NMR method for the calculation of the concentration of the species formed in solution has been provided, including the assessment of each of the fast exchanging proton species (whose nuclei resonate at the same chemical shifts in the NMR spectra). For this purpose, NMR-based calibration curves were utilized and an alternative method was applied for validation. The overall results showed that the amount of carbamate found at the equilibrium decreased as the length of the carbon chain increased, while the corresponding apparent carbamate decomposition equilibrium constants featured the same order of magnitude (10 −2).

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Section: Chemical Reactionssupporting

confidence: 92%

Section: Chemical Reactionsmentioning

confidence: 99%

Section: Rnh ][Hco ] [Rnhcoo ]mentioning

confidence: 99%

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NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture

Perinu

Arstad

Bouzga

et al. 2014

Ind. Eng. Chem. Res.

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“…The lone‐pair‐bearing molecules such as amines and carbenes show electron donating tendency toward the CO 2 molecule and significant research has been conducted on using polyamines as potential CO 2 capturing agents . Keeping this in view, we also study the intermolecular complexes of lone‐pair‐bearing molecules with CO 2 and investigate the structural and energetic features of these complexes in relation with the features of the lone pairs.…”

Section: Introductionmentioning

confidence: 99%

Electrostatics for probing lone pairs and their interactions

2017

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The value of the molecular electrostatic potential minimum (V ) and its topographical features (position, as well as the eigenvalues and eigenvectors of the corresponding Hessian matrix) are recently proposed as the criteria for characterizing a lone pair (Kumar A. et al., J. Phys. Chem. 2014, A118, 526). This electrostatic characterization of lone pairs is examined for a large number of small molecules employing MP4/6-311++G(d,p)//MP2/6-311++G(d,p) theory. The eigenvector of the Hessian matrix corresponding to its largest eigenvalue (λ ), is found to be directed toward the lone pair-bearing-atom, with λ showing a strong linear correlation with V . Large magnitudes of V and λ indicate a charge-dense lone pair. The topographical features of V are seen to provide insights into the interactive behavior of the molecules with model electrophiles, viz. HF, CO , and Li . In all the complexes of HF and majority of the other complexes, the interaction energy (E ) correlates well with the respective V value, but for some deviations occurring due to other competing secondary interactions. The electrostatic interactions are found to be highly directional in nature as the orientation of interacting atom correlates strongly to the position of lone pair. In summary, the present study on a large number of test molecules shows that electrostatics is able to probe lone pairs in molecules and offers a simple interpretation of chemical reactivity. © 2017 Wiley Periodicals, Inc.

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“…Peak at 75 ppm refers to the presence of residual glucose in the solution phase[36]. Amine groups occur at resonances δ= 37 -50 ppm typical for several aliphatic carbon structures[37]. There were a broad combination of peaks in this area and therefore it was difficult to confirm clear presence of amine from NMR spectra.…”

mentioning

confidence: 99%

Soy protein directed hydrothermal synthesis of porous carbon aerogels for electrocatalytic oxygen reduction

Alatalo

Qiu

Preuß

et al. 2016

Carbon

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¹³C and ¹⁵N NMR Characterization of Amine Reactivity and Solvent Effects in CO₂ Capture

Abstract: Factors influencing the reactivity of selected amine absorbents for carbon dioxide

Cited by 26 publications

References 31 publications

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture

Electrostatics for probing lone pairs and their interactions

Soy protein directed hydrothermal synthesis of porous carbon aerogels for electrocatalytic oxygen reduction

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13C and 15N NMR Characterization of Amine Reactivity and Solvent Effects in CO2 Capture

Abstract: Factors influencing the reactivity of selected amine absorbents for carbon dioxide

Cited by 26 publications

References 31 publications

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO2 Capture

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO2 Capture

Electrostatics for probing lone pairs and their interactions

Soy protein directed hydrothermal synthesis of porous carbon aerogels for electrocatalytic oxygen reduction

Contact Info

Product

Resources

About

¹³C and ¹⁵N NMR Characterization of Amine Reactivity and Solvent Effects in CO₂ Capture

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture

NMR-Based Carbamate Decomposition Constants of Linear Primary Alkanolamines for CO₂ Capture