Thermochemistry of hydrogen bonding of linear and cyclic amides in proton acceptors media

Rakipov, Ilnaz T.; Sabirzyanov, Almaz N.; Petrov, Аrtem А.; Akhmadiayrov, A. A.; Varfolomeev, Mikhail A.; Solomonov, Boris N.

doi:10.1016/j.tca.2017.03.016

Cited by 16 publications

(8 citation statements)

References 36 publications

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“…Using the data from Table 2 and Equation (2) the specific interaction enthalpies of cyclic amides in proton acceptor solvents were calculated; the results are presented in Table 3 . It was found that the hydrogen bond enthalpies of cyclic amides in proton acceptor solvents, calculated using Equation (2), are comparable to the hydrogen bond enthalpies of other amides estimated earlier in [ 16 ].…”

Section: Resultssupporting

confidence: 76%

“…The solution enthalpies of cyclic amides in proton acceptors are presented in Table 1 . The solution enthalpies of γ -butyrolactam and N -methylbutyrolactam in proton acceptor solvents were taken from [ 16 ].…”

Section: Resultsmentioning

confidence: 99%

“… a Standard uncertainties u are u (T) = 0.01 K, u (p) = 10 kPa. b Enthalpies of hydrogen bonding of γ -butyrolactam in solvent taken from work [ 16 ]. …”

Section: Tablementioning

confidence: 99%

“…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 linear amides are defined by the number of proton donor centers in the molecule [ 15 ]. The thermochemistry of hydrogen bonding of linear and cyclic amides with proton acceptor solvents was studied in [ 16 ]. 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.…”

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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Section: Resultssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 99%

“… a Standard uncertainties u are u (T) = 0.01 K, u (p) = 10 kPa. b Enthalpies of hydrogen bonding of γ -butyrolactam in solvent taken from work [ 16 ]. …”

Section: Tablementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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Introduction to Pyrrolidone and Caprolactam Chemistry

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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Pyrrolidones and caprolactams are important structural components of solvents, surfactants, polymers, natural products, and pharmaceuticals. This chapter provides an introduction to the structure, conformation, physical properties and reactivity of pyrrolidones and caprolactams. It begins with an overview of the nomenclature of lactams since there are several systems of nomenclature in practice, plus common names and various syncretisms. Next, the structures of pyrrolidone and caprolactam are discussed, starting with the X-ray crystal structures of pyrrolidone, N-methylpyrrolidone (NMP) and caprolactam. The conformational flexibility and ring strain of the two ring systems are also covered.Physical properties, such as dipole moments, the enthalpies of formation, vaporization and fusion, boiling points and melting points, are described. An attempt is made to put the properties of pyrrolidones and caprolactams into context with those of other lactams, amides and even lactones and cyclic ketones. Brønsted and Lewis basicity, acidity, hydrogen bonding and solubility are covered.Finally, a brief description of the basic reactivity of pyrrolidones and caprolactams is given. Topics covered are N-, O-, and α-C-alkylation, hydrolysis, reactions with organometallics, reduction, oxidation, and ring-opening polymerization. The intent is to give a concise physical organic perspective on reactivity (and stability) more than an extended treatise on synthetic elaborations. Definition and Nomenclature of LactamsLactams are cyclic amides in which both the carbonyl carbon and nitrogen atom of the amide group are part of a ring. The name, lactam, is a portmanteau of lactone (cyclic ester) and amide.Nomenclature of lactams follows a variety of conventions (Figure 1 and Table 1). The International Union of Pure and Applied Chemistry (IUPAC) recommends naming lactams as heterocyclic pseudoketones (IUPAC method 1) or by substituting lactam for the

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Introduction to Pyrrolidone and Caprolactam Chemistry

Chenault¹

2022

Handbook of Pyrrolidone and Caprolactam Based Materials

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Thermochemistry of hydrogen bonding of linear and cyclic amides in proton acceptors media

Cited by 16 publications

References 36 publications

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

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

Introduction to Pyrrolidone and Caprolactam Chemistry

Introduction to Pyrrolidone and Caprolactam Chemistry

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