An FT-IR study on intramolecular hydrogen-bonding in ethylene glycol derivatives

Singelenberg, F.A.J.; Maas, J.H. van der; Kroon-Batenburg, Loes M. J.

doi:10.1016/0022-2860(91)87095-y

Cited by 25 publications

(12 citation statements)

References 12 publications

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“…It was hardly possible to find any significant oxidation band at around 1 700-1 760 cm À1 within 24 h for both diols (shown in Figure 2(A)). FT-IR spectra for the PEG200 series (P2-1 to P2-5) (Figure 2(A) and (B)) were characterized by strong peaks at 3 450, 2 870 and 1 060 cm À1 , the former two being attributable to stretching bands of hydroxyl and the later band to ether oxygen groups, respectively, [20,21] whereas those of the F127 series (S1 to S5) (Figure 2(A) and 2(C)) showed distinctive stretching peaks at 2 880 and 1 100 cm À1 . Ether oxygen groups are along the main chains and are considered as an internal standard of non-oxidized groups.…”

Section: Resultsmentioning

confidence: 99%

“….O stretching vibration, where the intensities depend upon intramolecular or intermolecular hydrogen bonding. [20,21] Because there is a much lower population of OH groups in the F127 chains, the H bonding relevant -OH stretching bands at around 3 500 cm À1 are hardly seen. Although there are some alternations of intensity in the hydroxyl bands, it is not readily possible to see significant changes in the Milder Changes in Chemistry Make a Significant Difference in .…”

Section: Resultsmentioning

confidence: 99%

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Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains

Zhang

Easteal

2008

Macro Chemistry & Physics

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Here we report a simple oxidative route to making triblock copolymers with significantly higher phase transition temperatures than their precursor analogs at the same wt.‐% in water. This may be the easiest way to tune the phase transition temperatures of other analogs of Pluronic copolymers. Self‐capped triblock copolymers were synthesized, starting with Pluronic F127, using a milder selective oxidizer, to confer a near one‐fold increase in phase transition temperatures and alternative textures of the hydrogel surface in 30 wt.‐% copolymer. Comparison between the Pluronic triblock copolymer F127 and the end‐capped triblock copolymers was carried out using XPS, XRD, FT‐IR, environmental scanning electron microscopy (ESEM), polarization microscopy (PM) and NMR, though the change in chemistry was small. The present work provides a paradigm that a long macromolecular chain with a slightly modified chemistry may lead to huge alterations in the properties of materials which have potential applications in environmental monitoring, sensors, tissue engineering, artificial skin and drug delivery, particularly in injectable gel delivery systems.magnified image

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains

Zhang

Easteal

2008

Macro Chemistry & Physics

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“…Hydroxyl H‐bonds can be studied experimentally using techniques such as infrared (IR) spectroscopy (due to OH stretching vibrations sensitivity to inter‐ and intra‐molecular interactions). Reported experiments on TEG mono‐methyl ether have measured vibrational frequencies at 3642 cm −1 corresponding to the OH bond, as well as frequencies at 3607, 3488, and 3523cm −1 , corresponding to H‐bonds between hydroxyl and ether oxygens of the molecule, thus showing the presence of H‐bonds in a liquid similar to TEG. Furthermore, it has also been shown by reported IR‐spectroscopy experiments that OH stretching vibrations of the OH‐donor of TEG mono‐methyl ether are dependent on the surrounding solvent .…”

Section: Introductionmentioning

confidence: 99%

Hydrogen bond lifetimes and statistics of aqueous mono‐, di‐ and tri‐ethylene glycol

Olsen

Kvamme

2016

AIChE Journal

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Hydrogen bond statistics, energy distributions of hydrogen bonds and hydrogen bond lifetimes for aqueous monoethylene glycol (MEG), diethylene glycol (DEG), and triethylene glycol (TEG) were investigated at temperatures ranging from 275 to 370 K at 101.325 kPa using molecular dynamics simulations. Each individual type of hydrogen bond were studied separately to better understand how each type of hydrogen bond affected the collective behavior often measured in experiments. We also studied the effects of glycols on water–water hydrogen bond structures and lifetimes. Decay constants for hydroxyl type hydrogen bonds, as well as for water based hydrogen bonds were in the same order, thus indicating that all these hydrogen bonds play an essential role in the process of dielectric relaxation. Correlations between water hydrogen bond distances and angles were not affected markedly by adding glycols. However, hydrogen bond lifetimes increased by 9, 29, and 62 times by adding MEG, DEG, and TEG, respectively. © 2016 American Institute of Chemical Engineers AIChE J, 63: 1674–1689, 2017

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“…Hydrogen bond energies range from 1 to 4 kcal mol −1 for weak bonds through to ∼15–40 kcal mol −1 for strong bonds . Intramolecular H‐bonds in ethylene glycol derivatives are comparatively larger (∼13.7–15.9 kcal mol −1 ) than intramolecular H‐bonding in proteins (∼6–8 kcal mol −1 for N‐H‐‐‐O=C and ∼1.5–1.8 kcal mol −1 for C α ‐H‐‐‐O=C interactions). The observed blue‐shift from ∼3280 to 3290 cm −1 upon heating suggests that the N‐H and O‐H groups in the sample are located within weaker or non H‐bonded environments …”

Section: Resultsmentioning

confidence: 99%

Changes in hydrogen bonding in protein plasticized with triethylene glycol

Hicks

Verbeek

Lay

et al. 2015

J of Applied Polymer Sci

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Bloodmeal decolored with 4 wt % peracetic acid can be extruded into a semi-transparent bio-plastic through the addition of sodium dodecyl sulfate (SDS), water, and triethylene glycol (TEG). TEG is often used to plasticize protein thermoplastic materials because of its ability to form both hydrophobic and hydrogen bonds. Synchrotron-based FT-IR was used to monitor changes in the types of hydrogen bonding occurring in TEG plasticized protein during heating. Heating was found to overcome a portion of the weaker hydrogen bonds found within and between proteins, observed as a blue-shift in the N-H and O-H stretching vibrations occurring at 3280 cm 21 . TEG was shown to be involved in a larger array of hydrogen bonding environments after heating, evidenced by the broadening of the C-OH stretch around 1076 cm 21 , suggesting improved plasticizer-protein interactions. Additionally, these bonds were found to be as strong as the original interactions, observed as a shift in the C-OH peak back to its original wavenumber (1076 cm 21 ) during cooling. Initially, TEG was spatially distributed into distinct plasticizer-rich and plasticizer-poor domains, giving rise to two glass transitions. Heating allowed the migration and uniform dispersion of TEG throughout the material, and merged the two glass transitions into one broader glass transition region. Heating during DSC removed the peak around 60 C corresponding to the enthalpy of relaxation, which is associated with physical aging of amorphous and semi-crystalline polymers. While physical aging occurred during the storage of DBM, in the presence of TEG it occurred to a lesser extent. V C 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42166.

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An FT-IR study on intramolecular hydrogen-bonding in ethylene glycol derivatives

Cited by 25 publications

References 12 publications

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains

Hydrogen bond lifetimes and statistics of aqueous mono‐, di‐ and tri‐ethylene glycol

Changes in hydrogen bonding in protein plasticized with triethylene glycol

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An FT-IR study on intramolecular hydrogen-bonding in ethylene glycol derivatives

Cited by 25 publications

References 12 publications

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO106‐PPO70‐PEO106 Block Copolymer Chains

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO106‐PPO70‐PEO106 Block Copolymer Chains

Hydrogen bond lifetimes and statistics of aqueous mono‐, di‐ and tri‐ethylene glycol

Changes in hydrogen bonding in protein plasticized with triethylene glycol

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Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains

Milder Changes in Chemistry Make a Significant Difference in Phase Transition Temperatures for Triblock Copolymers on PEO₁₀₆‐PPO₇₀‐PEO₁₀₆ Block Copolymer Chains