Enthalpy of cooperative hydrogen bonding in complexes of tertiary amines with aliphatic alcohols: Calorimetric study

Zaitseva, Ksenia V.; Varfolomeev, Mikhail A.; Novikov, Vladimir B.; Solomonov, Boris N.

doi:10.1016/j.jct.2011.02.019

Cited by 62 publications

(12 citation statements)

References 62 publications

(92 reference statements)

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“…The

parameter was calculated from the linear dependences of solution enthalpies of n-alkanes in solvents against the characteristic volume of n-alkanes. The detailed description of the approach and the examples of determining the contributions of non-specific intermolecular interactions of different solutes in solvents are presented in earlier works [ 14 , 15 , 22 , 29 , 30 , 31 , 32 ]. The specific relative cavity formation enthalpies of cyclohexane and benzene are 5.02 10 2 kJ∙cm −3 and 1.42∙10 2 kJ∙cm −3 [ 23 ], respectively.…”

Section: Resultsmentioning

confidence: 99%

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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“…The

Section: Resultsmentioning

confidence: 99%

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 alkylating rather than acylating the 4'-methylamine, the basicity of the nitrogen is predicted to be preserved, while also maintaining the nitrogen atom's ability to act as ah ydrogen bond acceptor. [25] In the work presented herein, alkylation of the 4'-methylamine has successfully generated af unctional probe that has retained high affinity.A sc ompound 8 has been demonstrated to bind reversibly to the ATPb inding site of PKA, it could be employed to demonstrate whether ak nown inhibitor binds in ac ompetitive or allosteric manner,a so nly competitive blockers are expected to displace compound 8. This wasc onfirmed using H-7, ac ompetitive blocker of the ATPb inding site on PKA.…”

Section: Discussionmentioning

confidence: 97%

“…Acylation of the amine introduces an electron‐withdrawing carbonyl group that greatly decreases the basicity of the nitrogen. In alkylating rather than acylating the 4′‐methylamine, the basicity of the nitrogen is predicted to be preserved, while also maintaining the nitrogen atom's ability to act as a hydrogen bond acceptor . In the work presented herein, alkylation of the 4′‐methylamine has successfully generated a functional probe that has retained high affinity.…”

Section: Discussionmentioning

confidence: 99%

Alkylation of Staurosporine to Derive a Kinase Probe for Fluorescence Applications

2016

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The natural product staurosporine is a high‐affinity inhibitor of nearly all mammalian protein kinases. The labelling of staurosporine has proven effective as a means of generating protein kinase research tools. Most tools have been generated by acylation of the 4′‐methylamine of the sugar moiety of staurosporine. Herein we describe the alkylation of this group as a first step to generate a fluorescently labelled staurosporine. Following alkylation, a polyethylene glycol linker was installed, allowing subsequent attachment of fluorescein. We report that this fluorescein–staurosporine conjugate binds to cAMP‐dependent protein kinase in the nanomolar range. Furthermore, its binding can be antagonised with unmodified staurosporine as well as ATP, indicating it targets the ATP binding site in a similar fashion to native staurosporine. This reagent has potential application as a screening tool for protein kinases of interest.

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“…This study continues our combined experimental and theoretical examination of gas-toorganic solvent transfer processes for nonelectrolyte solutes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Such processes govern chemical separations by gas-liquid chromatography, measurement of solubilities and activity coefficients by inert-gas stripping methods, and the removal and pre-concentration of volatile organic solutes from aqueous analytical samples using headspace single drop micro-extraction methods.…”

Section: Introductionmentioning

confidence: 91%

Effect of halogen substitution on the enthalpies of solvation and hydrogen bonding of organic solutes in chlorobenzene and 1,2-dichlorobenzene derived using multi-parameter correlations

et al. 2015

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Enthalpies of solution at infinite dilution at 298 K, ΔsolnH A/Solvent , have been measured by isothermal solution calorimetry for 43 and 72 organic solutes dissolved in chlorobenzene and 1,2-dichlorobenzene, respectively. The measured ΔsolnH A/Solvent data, along with published ΔsolnH A/Solvent values taken from the published literature for solutes dissolved in both chlorobenzene solvents, were converted to enthalpies of solvation, ΔsolvH A/Solvent , using standard thermodynamic equations. Abraham model correlations were developed from the experimental ΔsolvH A/Solvent data. The best derived correlations describe the experimental gas-to-chlorobenzene and gas-to-1,2-dichlorobenzene enthalpies of solvation to within standard deviations of 1.5 kJ mol -1 and 1.9 kJ mol -1 , respectively. Enthalpies of X-H…π (X -O, N, and C) hydrogen bond formation of proton donor solutes (alcohols, amines, chlorinated hydrocarbons and etc.) with chlorobenzene and 1,2-dichlorobenzene were calculated based on the Abraham solvation equation. Obtained values are in good agreement with the results determined using conventional methods.

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Enthalpy of cooperative hydrogen bonding in complexes of tertiary amines with aliphatic alcohols: Calorimetric study

Cited by 62 publications

References 62 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

Alkylation of Staurosporine to Derive a Kinase Probe for Fluorescence Applications

Effect of halogen substitution on the enthalpies of solvation and hydrogen bonding of organic solutes in chlorobenzene and 1,2-dichlorobenzene derived using multi-parameter correlations

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