The Polarity and Strength of the Intermolecular Hydrogen Bond

Gur'yanova, E. N.; Gol'dshtein, I. P.; Perepelkova, T. I.

doi:10.1070/rc1976v045n09abeh002715

Cited by 38 publications

(5 citation statements)

References 2 publications

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“…We speculate that the interfacial interaction of other functionalities in the polymers to surfaces also contributes to the realization of strong underwater bonding, since the polar–polar interactions and H-bonding between the those functional groups and the attached surface could not be ignored. Previous reports already verified that the higher polarity of polymer can lead to stronger H-bonding . Very interestingly, the dielectric constant of glass and Al 2 O 3 (the surface of Al is always covered by a layer of Al 2 O 3 ) is around 3.8 and 4.5, respectively, which matches quite well with the dielectric constant of polymer IV (3.3).…”

Section: Resultssupporting

confidence: 78%

“…Previous reports already verified that the higher polarity of polymer can lead to stronger H-bonding. 32 Very interestingly, the dielectric constant of glass and Al 2 O 3 (the surface of Al is always covered by a layer of Al 2 O 3 ) is around 3.8 and 4.5, respectively, which matches quite well with the dielectric constant of polymer IV (3.3). We also test the bonding strength of the four polymers on PTFE, a substrate with a very low surface energy, and the results were shown in Figure S11.…”

Section: ■ Results and Discussionsupporting

confidence: 59%

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Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Pei

et al. 2017

ACS Biomater. Sci. Eng.

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Although the role of 3,4-dihydroxyphenyl-L-alanine(DOPA)in mussel foot proteins (mfps) in the realization of underwater bonding has been widely recognized, the role of the polarity of the polymer was largely overlooked. Here, by systematically comparing the underwater bonding properties of four mussel-inspired adhesives with different amide/lactam contents but similar catechol contents and molecular weights, we came to the conclusion that the polarity of the polymers also contributes to the strong underwater bonding. With the increase in the amide/lactam contents, the polarity of the polymeric adhesive increases, which correlates to the improved underwater bonding strength. A dielectric constant is introduced to evaluate the polarity of the polymer, which may be used as a guidance for the design of mussel-inspired adhesives with even better underwater bonding properties.

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Section: Resultssupporting

confidence: 78%

Section: ■ Results and Discussionsupporting

confidence: 59%

Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Pei

et al. 2017

ACS Biomater. Sci. Eng.

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“…The magnitudes of the −Δ H formation values measured in the present work are consistent with values for strong hydrogen bond complexes reported in the literature. In the past, calorimetry has been used to measure the −Δ H formation of a number of hydrogen bonded acid/base complexes, including compounds similar to those in this study such as pyridine or pyridine−oxides and substituted acetic acids . The enthalpies (11−24 kcal) obtained here for nonylamine (p K a 10.13) are consistent with the values for triethylamine (p K a 10.7) with the series of carboxylic acids.…”

Section: Discussionsupporting

confidence: 76%

Enthalpic Studies of Complex Formation between Carboxylic Acids and 1-Alkylimidazoles

1998

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The nature of the hydrogen bonding in complexes of alkylimidazoles and substituted carboxylic acids has been studied as a model of the hydrogen-bonding interaction of the proton bridging Nδ1 of His 57 and the β carboxyl group of Asp 102 in the active site of chymotrypsin. The interaction has been postulated to be a low barrier hydrogen bond (LBHB) in the enzyme and also in the model complexes which have a small ΔpK a. In the present study, enthalpies of complex formation, −ΔH formation, between alkylimidazoles (1-methyl, 1-n-butyl-, and 1-tert-butylimidazole) and a series of carboxylic acids were determined by adiabatic solution calorimetry in chloroform. In FTIR studies presented here, the concentration of LBHB present in these complexes was determined. For complexation between dichloropropionic acid and alkylimidazoles for which the ΔpK a is small in chloroform, the −ΔH formation values varied from 12 to 15 kcal/mol. Thus in enzymes, where ΔG is similar to ΔH, ΔG formation can be as high as −12 to −15 kcal/mol for LBHBs. If a weak hydrogen bond in the initial E·substrate complex with a ΔG formation of ≤−5 kcal/mol is converted to a low barrier hydrogen bond in the transition state, there will be 7−10 kcal/mol of energy available to lower the activation barrier and accelerate the reaction by 5−7 orders of magnitude.

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“…224–225 °C; 4 , mp. 167–169 °C) and the different Rf values ( 3 , Rf ≈ 0.2; 4 , Rf ≈ 0.4, solvents: petroleum ether/ethyl acetate = 2/3) in thin layer chromatography, we assumed that triol 3 tends to form an intermolecular hydrogen bonding interaction between the 12‐OH and tetrahydrofuran ring, while the ( R )‐epimer 4 is more apt to be involved in intramolecular hydrogen bonding . This hydrogen bonding interaction may affect the accessibility of hydrogen bond donors/acceptors to the 12‐OH and E‐ring of the epimers.…”

Section: Resultsmentioning

confidence: 99%

Novel 3‐Substituted Ocotillol‐Type Triterpenoid Derivatives as Antibacterial Candidates

Zhang

et al. 2014

Chem Biol Drug Des

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Plant-derived triterpenoid saponins are involved in the plant defense system by targeting bacterial membranes. A series of ocotillol-type triterpenoid derivatives were synthesized starting from PPD, one of the main components of Panax ginseng and their antibacterial activity against several representative bacteria were evaluated. Compounds 5 and 11 exhibited excellent antibacterial activity with MIC values of 1 μg/mL against Staphylococcus aureus and 8 μg/mL and 4 μg/mL against Bacillus subtilis, respectively. Furthermore, when compounds 5 and 11 were combined with two commercial antibiotics kanamycin and chloramphenicol, they showed strong synergistic activity at sub-MIC levels against S. aureus USA300 and B. subtilis 168. Moreover, chloramphenicol turned from a bacteriostatic to a bactericidal agent when combined with compound 11 against B. subtilis 168.

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The Polarity and Strength of the Intermolecular Hydrogen Bond

Cited by 38 publications

References 2 publications

Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Contribution of the Polarity of Mussel-Inspired Adhesives in the Realization of Strong Underwater Bonding

Enthalpic Studies of Complex Formation between Carboxylic Acids and 1-Alkylimidazoles

Novel 3‐Substituted Ocotillol‐Type Triterpenoid Derivatives as Antibacterial Candidates

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