SPECTROSCOPIC STUDIES OF ALCOHOLS: VI. INTRAMOLECULAR HYDROGEN BONDS IN ETHANOLAMINE AND ITS <i>O</i>- AND <i>N</i>-METHYL DERIVATIVES

Krueger, P. J.; Mettee, Howard D.

doi:10.1139/v65-411

Cited by 77 publications

(31 citation statements)

References 19 publications

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“…In the gas phase and in non-polar weakly interacting solvents, ethanolamine molecules can adopt various conformations resulting in intramolecularly hydrogen-bonded and non-bonded amino and hydroxyl groups that are spectroscopically distinguishable [35][36][37]. An IR spectrum recorded in the gas phase therefore features a number of absorption bands between 3550 and 3670 cm −1 that are assigned to the "free" and the "bound" OH-groups of these various conformers.…”

Section: Resultsmentioning

confidence: 99%

“…An IR spectrum recorded in the gas phase therefore features a number of absorption bands between 3550 and 3670 cm −1 that are assigned to the "free" and the "bound" OH-groups of these various conformers. In addition, NH-stretching absorptions were identified around 3420 cm −1 [35][36][37]. A Fourier transform infrared spectrum (FTIR) emphasizing the entire stretching spectral region of liquid ethanolamine from 2500 to 3500 cm −1 is displayed in Fig.…”

Section: Resultsmentioning

confidence: 99%

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OH and NH Stretching Vibrational Relaxation of Liquid Ethanolamine

Knop

Lindner

Vöhringer³

2011

Zeitschrift Für Physikalische Chemie

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Vibrational Relaxation / Liquid Dynamics / Hydrogen-Bonding / Ultrafast SpectroscopyFemtosecond mid-infrared pump-probe spectroscopy was carried out to obtain information about the dynamics of vibrational energy relaxation in liquid ethanolamine at room temperature and ambient pressure. Through partial deuteration it was possible to disentangle the dynamics resulting from the OH and the NH stretching modes that proceed independently and simultaneously in the hydrogen-bonded liquid following an ultrafast vibrational excitation by a resonant mid-infrared pulse. The OH-stretching vibrational lifetime was determined to be 450 fs while the NH-stretching lifetime was found to be 1.2 ps. This large difference in lifetimes highlights the importance of the hydrogen-donating and the hydrogen-accepting character of the vibrating groups that are engaged in hydrogen-bonding.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

OH and NH Stretching Vibrational Relaxation of Liquid Ethanolamine

Knop

Lindner

Vöhringer³

2011

Zeitschrift Für Physikalische Chemie

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“…A similar sort of comparison may be attempted in the N,N-dimethylamino series.. We have previously determined the enthalpy of the intramolecular H-bond in cis-2-aminocyclopentanol (5) to be -1.92 kcal mol-I (3a). utilizing similar techniques and solvents (15) we have now determined the AH values for the H-bonds of cis-and trans-2-aminocyclohexanol (1 and 2) to be -2.5 kcal mol-I and -2.8 kcal mol-I respectively. Hence it seems clear that the magnitude of the spectral shifts obtained for these compounds from Table 1 correlates in no simple way with the enthalpies of H-bonding.…”

Section: Aminocyclanolsmentioning

confidence: 99%

“…We have not attempted to see if a correlation exists between the enthalpy of the H-bond and the induced pe spectral shifts in comparison to 12 since none of those compounds in which an intramolecularlybonded OH stretching frequency is observed exhibit a free -OH stretch, thus precluding enthalpy measurements (15). As in the case of the 2-aminocyclanols however, it is not likely that such a correlation will exist since the spectral shifts in the g-bonding region, which undoubtedly represent major electronic changes in the C-C, C-0-, and C-H skeleton, defy analysis.…”

Section: Methoxycyclanolsmentioning

confidence: 99%

Application of photoelectron spectroscopy to intramolecularly hydrogen-bonded systems. Part III. The photoelectron spectra of cis and trans 2-substituted cyclopentanols and cis and trans 2-substituted cyclohexanols

Brown¹

1976

Can. J. Chem.

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R. S. BROWN. Can. J. Chem. 54,1929Chem. 54, (1976. The photoelectron spectra of several well defined molecules exhibiting intramolecular hydrogen bonding has been determined and the analysis of the spectra is in accord with recent molecular orbital calculations of related systems. The experimentally determined enthalpies of the hydrogen bonds in cis-2-aminocyclopentanol and cis-and trans-2-aminocyclohexanol d o not correlate in any simple fashion with the shifts in the ionization energies of the no and nN orbitals compared t o a model which precludes hydrogen bonding. The spectral differences attributed to hydrogen bonding in the cis and tratls 2-substituted cyclanols cannot be attributed to differences in the through-bond interaction of the n orbitals on either atom since the cis and trarrs isomers of 1,2-dimethoxycyclopentane and 1,2-dimethoxycyclohexane show virtually identical pe spectra. A discussion of the applicability of Koopmans' theorem and the effect of the hydrogen bond in both the ion and ground states is presented.

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“…One may expect intramolecular H-bonds as known for similar molecules (2-amino-ethanol), where preferably the N • • • H -O bond is established by the isolated molecule [1] and occurs also in dilute solution [2], In the pure liquid state a variety of intermolecular H-bonds is feasible, the N…”

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confidence: 99%

Dielectric Relaxation of 2-Amino-l-butanol

Witt

Stockhausen

Jadżyn

et al. 1992

Zeitschrift Für Naturforschung A

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The dielectric relaxation spectrum of the title substance in mixtures with 1,4-dioxane or benzene (pure liquid to moderate mixture ratios) is measured between 5 MHz and 36 GHz at 20°C. The static permittivity is determined over the whole mixture range. The results are discussed in particular with respect to the possibility that different types of hydrogen bonded aggregations may contribute to the main relaxation.The 2-amino-l-butanol molecule offers several hydrogen bonding possibilities. One may expect intramolecular H-bonds as known for similar molecules indicates a correspondingly complex association behaviour by exhibiting a comparably broad main absorption region, which is just the region usually related to self-association, while the high frequency side of the spectrum resembles that normally found with alcohols, its moderate slope indicating subsequent but less intense relaxation contributions. There is no influence of the stereoisomeric composition on the spectrum [3]. It is a question whether the main absorption incorporates overlapping absorptions ascribable to dielectrically distinguishable types of self-association (so that its formal description by discrete spectral components rather than by a continuous distribution of relaxation times would be appropriate). Information in that respect may be gained from the eventual alteration of the relaxation spectrum on dilution of the alcohol by a nonpolar solvent. We have therefore studied the relaxation behaviour and the static dielectric properties of 2-aminol-butanol in mixtures with 1,4-dioxane and benzene.The absorption quantity e"(co) was measured at 10 spot frequencies ranging between 5 MHz and 36 GHz.Reprint requests to Prof. M. Stockhausen, Institut für Physikalische Chemie der Universität, Schloßplatz 4, W-4400 Münster (Germany).The temperature was 20 °C. For reasons of sensitivity the alcohol mole fraction x alc >0.4. The static permittivity e s , on the other hand, was measured over the whole mixture range (x alc >0.01), either at 1.5 kHz (with a Wayne-Kerr B330 bridge) or 5 MHz (with a Wayne-Kerr B 801B bridge), depending on the alcohol content being lower or higher than x alc « 0.4, respectively. The density g, viscosity A/ and refractive index n D were determined in addition.The E" (CO) data (after correction for the conductivity contribution) were fitted by a sum of discrete Debye type spectral components C ; . A minimum number of four components is necessary for satisfactory fits covering the experimental frequency range. Their parameters, i.e. relaxation times T ; and relaxation strengths are represented graphically in Figs, la and 1 b. The relaxation strenghts are normalized to the alcohol concentration, viz. S t c alc /c alc , the asterisk indicating the pure liquid. In Figs. 1 a, b the size of the symbols corresponds roughly to the acceptable variability range of the parameters (only the minor high frequency component C 4 is somewhat less accurately defined). From the static e s data we calculated the apparent dipole moment p app accordin...

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SPECTROSCOPIC STUDIES OF ALCOHOLS: VI. INTRAMOLECULAR HYDROGEN BONDS IN ETHANOLAMINE AND ITS O- AND N-METHYL DERIVATIVES

Abstract: The competitive intran~olecular O H . .

Cited by 77 publications

References 19 publications

OH and NH Stretching Vibrational Relaxation of Liquid Ethanolamine

OH and NH Stretching Vibrational Relaxation of Liquid Ethanolamine

Application of photoelectron spectroscopy to intramolecularly hydrogen-bonded systems. Part III. The photoelectron spectra of cis and trans 2-substituted cyclopentanols and cis and trans 2-substituted cyclohexanols

Dielectric Relaxation of 2-Amino-l-butanol

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