The dissociation energy of the gaseous methanol-diethyl ether complex

Inskeep, Richard G.; Dickson, Frank E.; Kelliher, James M.

doi:10.1016/0022-2852(60)90110-7

Cited by 13 publications

(5 citation statements)

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“… a Experimental values. b Ref . c Ref . d Ref . e Ref . f Complex with methanol as acceptor of the hydrogen bond. …”

Section: Resultsmentioning

confidence: 99%

“…Appropriate references for the present study are the complexes in the gas phase because they are not affected by their surroundings (solvent in solution or other molecules in solids). The structure of such complexes was investigated by microwave spectroscopy or rotationally resolved laser-induced fluorescence spectroscopy. − Formation and the properties of the complexes are often studied with different methods of the vibrational spectroscopy: infrared (IR), Raman, − jet FTIR, − jet Raman, IR cavity ringdown spectroscopy, IR-depletion spectroscopy, , and so on. Most often, the red shift of the stretching OH vibrations are followed, but in some cases, also low frequency vibrational modes have been measured by spectral hole burning and disperse fluorescence spectroscopy. , The stability of the complexes of methanol with different amines, phenol, methanol, and so on have been determined by thermodynamic measurements, , IR, − NMR, or TOF mass spectrometry with laser excitation .…”

Section: Introductionmentioning

confidence: 99%

“…The structure of such complexes was investigated by microwave spectroscopy or rotationally resolved laser-induced fluorescence spectroscopy. − Formation and the properties of the complexes are often studied with different methods of the vibrational spectroscopy: infrared (IR), Raman, − jet FTIR, − jet Raman, IR cavity ringdown spectroscopy, IR-depletion spectroscopy, , and so on. Most often, the red shift of the stretching OH vibrations are followed, but in some cases, also low frequency vibrational modes have been measured by spectral hole burning and disperse fluorescence spectroscopy. , The stability of the complexes of methanol with different amines, phenol, methanol, and so on have been determined by thermodynamic measurements, , IR, − NMR, or TOF mass spectrometry with laser excitation . In some of the studies the structural parameters, vibrational frequencies, and binding energies, measured experimentally, were supplemented by simulations with computational methods at different levels HF, DFT, MP2, MP4, and CI. ,,,,,− Where appropriate, we compared our results with those reported previously.…”

Section: Introductionmentioning

confidence: 99%

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Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups

et al. 2011

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Various hydrogen-bonded complexes of methanol with different proton accepting and proton donating molecules containing Cl, F, NH(2), OH, OR, and COOH functional groups have been modeled using DFT with hybrid B3LYP and M05-2X functionals. The latter functional was found to provide more accurate estimates of the structural and thermodynamic parameters of the complexes of halides, amines, and alcohols. The characteristics of these complexes are influenced not only by the principle hydrogen bond of the methanol OH with the proton acceptor heteroatom, but also by additional hydrogen bonds of a C-H moiety with methanol oxygen as a proton acceptor. The contribution of the former hydrogen bond in the total binding enthalpy increases in the order chlorides < fluorides < alcohols < amines, while the contribution of the second type of hydrogen bond increases in the reverse order. A general correlation was found between the binding enthalpy of the complex and the electrostatic potential at the hydrogen center participating in the formation of the hydrogen bond. The calculated binding enthalpies of different complexes were used to clarify which functional groups can potentially form a hydrogen bond to the 2'-OH hydroxyl group in ribose, which is strong enough to block it from participation in the intramolecular catalytic activation of the peptide bond synthesis. Such blocking could result in inhibition of the protein biosynthesis in the living cell if the corresponding group is delivered as a part of a drug molecule in the vicinity of the active site in the ribosome. According to our results, such activity can be accomplished by secondary or tertiary amines, alkoxy groups, deprotonated carboxyl groups, and aliphatic fluorides, but not by the other modeled functional groups.

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“… a Experimental values. b Ref . c Ref . d Ref . e Ref . f Complex with methanol as acceptor of the hydrogen bond. …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups

et al. 2011

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“…A linear correlation between AH and the intensity of the OH stretching band of the complex was also noted. Other systems studied in which heats of formation values were derived were: acetic acid, butyric acid (237); methanol-ethyl ether (136); caprolactam (182); methanol-OD (137); pyrazole (2); imidazole (3); phenol, p-cresol, p-chlorophenol (187).…”

Section: Intensitiesmentioning

confidence: 99%

Infrared Spectometry

Evans¹

1962

Anal. Chem.

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Whileit is hoped that in this review most of the fundamental developments in infrared spectroscopy which appeared in the literature during the two-year period prior to November 1961 are discussed, it is immediately admitted that much interesting material has not been included. This is partly a reflection of the reviewer's interests, but it is also probable that much was inadvertently overlooked. Useful new data, usually in the form of spectra used in confirming molecular structures, appear in many papers devoted to organic chemistry, but the spectroscopic data are frequently not mentioned

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“…These include nuclear magnetic resonance spectroscopy, 19,20 microwave spectroscopy, 21 pressure measurements [22][23][24][25] and IR spectroscopy. 24,[26][27][28][29][30][31][32][33][34] In most of these studies a van't Hoff type of equation is used to determine DH. 35 For example, the DH value of the complex formation between methanol and trimethylamine has been determined in several different temperature studies.…”

Section: Introductionmentioning

confidence: 99%

Accurate thermodynamic properties of gas phase hydrogen bonded complexes

Hansen

Maroun

Mackeprang

et al. 2016

Phys. Chem. Chem. Phys.

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We have measured the infrared spectra of ethanol·dimethylamine and methanol·dimethylamine complexes in the 299-374 K temperature range, and have determined the enthalpy of complex formation (ΔH) to be -31.1 ± 2 and -29.5 ± 2 kJ mol(-1), respectively. The corresponding values of the Gibbs free energy (ΔG) are determined from the experimental integrated absorbance and a calculated oscillator strength of the OH-stretching vibrational transition to be 4.1 ± 0.3 and 3.9 ± 0.3 kJ mol(-1) at 302 and 300 K, respectively. The entropy, ΔS is determined from the values of ΔH and ΔG to be -117 ± 7 and -111 ± 10 J (mol K)(-1) for the ethanol·dimethylamine and methanol·dimethylamine complexes, respectively. The determined ΔH, ΔG and ΔS values of the two complexes are similar, as expected by the similarity to their donor molecules ethanol and methanol. Values of ΔH, ΔG and ΔS in chemical reactions are often obtained from quantum chemical calculations. However, these calculated values have limited accuracy and large variations are found using different methods. The accuracy of the present ΔH, ΔG and ΔS values is such that the benchmarking of theoretical methods is possible.

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The dissociation energy of the gaseous methanol-diethyl ether complex

Cited by 13 publications

References 1 publication

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups

Infrared Spectometry

Accurate thermodynamic properties of gas phase hydrogen bonded complexes

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The dissociation energy of the gaseous methanol-diethyl ether complex

Cited by 13 publications

References 1 publication

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH2, OH, and COOH Functional Groups

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH2, OH, and COOH Functional Groups

Infrared Spectometry

Accurate thermodynamic properties of gas phase hydrogen bonded complexes

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Product

Resources

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Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups

Density Functional Study of Hydrogen Bond Formation between Methanol and Organic Molecules Containing Cl, F, NH₂, OH, and COOH Functional Groups