Thermochemistry of hydrogen bonding of proton acceptors in the media of linear and cyclic amides. Cooperativity effects in multi-particle complexes of amides

Rakipov, Ilnaz T.; Petrov, Аrtem А.; Akhmadiyarov, Aydar A.; Khachatrian, Artashes A.; Varfolomeev, Mikhail A.; Solomonov, Boris N.

doi:10.1016/j.tca.2017.09.012

Cited by 8 publications

(10 citation statements)

References 63 publications

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“…In this case, studies on associated solvents, including water, are of particular interest. Earlier, our group actively studied the intermolecular interactions of structural fragments of dipeptides and proteins (linear and cyclic amides) [ 12 , 13 , 14 , 15 , 16 ]. The effect of the number of active proton donor centers of linear amides on their proton donor properties in solution was shown [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

The Solvation Effect of C=O Group of Cyclic Anhydrides in Solution

Rakipov

Akhmadiyarov

Petrov

et al. 2023

IJMS

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The paper reports the results of investigation intermolecular interactions between alanine and sarcosine anhydride in organic solvents. The absorption frequencies of cyclic dipeptide in solvents were measured by IR spectroscopy. The effect of Van der Waals interactions and the hydrogen bonding of solvents on absorption frequencies of the C=O group of anhydrides was discussed. The spectroscopic parameters for C=O∙∙∙H-O hydrogen bonding complexes of anhydride with methanol in aprotic and proton donor solvent are obtained. In multi-particle complexes of dipeptides with aliphatic alcohols, the hydrogen bond enhancement was between 10 and 16%, which is significantly lower than it is for amide complexes.

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Section: Introductionmentioning

confidence: 99%

The Solvation Effect of C=O Group of Cyclic Anhydrides in Solution

Rakipov

Akhmadiyarov

Petrov

et al. 2023

IJMS

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“…[5][6][7][8][9][10][11][12][13] Spectroscopic analysis of gas phase complexes conrms these predictions. 14 These effects are likely to have important implications for understanding the properties of a wide range of different systems, because chains of Hbonded amides are a common motif in protein structure and polyamide materials. Cite this: DOI: 10.1039/d2sc04271a…”

Section: Introductionmentioning

confidence: 99%

H-bond cooperativity: polarisation effects on secondary amides

et al. 2022

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“…The intermolecular interactions of linear and cyclic amides in the solutions were studied following the approach based on solvation thermochemistry [ 15 , 16 , 17 ]. The proton donor properties of linear amides are defined by the number of proton donor centers in the molecule [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

“…The proton donor properties of 2-pyrrolidone were shown to be more pronounced than that of the linear amides; thus, the cyclic configuration of amide enhances its proton donor properties. The intermolecular interactions of proton acceptors in the linear and cyclic amides media were also researched [ 17 ]. The hydrogen bonding enthalpies of proton acceptors in N -methylformamide and 2-pyrrolidone are significantly lower than the enthalpies of hydrogen bonding of amide-base systems in 1:1 complexes.…”

Section: Introductionmentioning

confidence: 99%

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Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect

et al. 2021

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In the present work, the thermochemistry of solution, solvation, and hydrogen bonding of cyclic amides in proton acceptor (B) and proton donor (RXH) solvents were studied. The infinite dilution solution enthalpies of δ-valerolactam, N-methylvalerolactam, ε-caprolactam, and N-methylcaprolactam were measured at 298.15 K. The solvation enthalpies of cyclic amides were calculated based on the measured solution enthalpies and sublimation/vaporization enthalpies from literature. The enthalpies of hydrogen bonding between cyclic amides and proton acceptor and donor solvents were then calculated as a difference between the total solvation enthalpy and the non-specific contribution. The latter was estimated via two different approaches in proton donor and proton accepting solvents. The effect of the cycle size on the strength of hydrogen bonding of the cyclic amides in solution is discussed.

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Thermochemistry of hydrogen bonding of proton acceptors in the media of linear and cyclic amides. Cooperativity effects in multi-particle complexes of amides

Cited by 8 publications

References 63 publications

The Solvation Effect of C=O Group of Cyclic Anhydrides in Solution

The Solvation Effect of C=O Group of Cyclic Anhydrides in Solution

H-bond cooperativity: polarisation effects on secondary amides

Thermochemistry of Solution, Solvation, and Hydrogen Bonding of Cyclic Amides in Proton Acceptor and Donor Solvents. Amide Cycle Size Effect

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