Mechanism of proton transfer in the strong OHN intermolecular hydrogen bond

RSC Advances ◽  
2011 ◽  
Vol 1 (2) ◽  
pp. 219 ◽  
Author(s):  
Irena Majerz ◽  
Matthias J. Gutmann
Keyword(s):  
Hydrogen Bond ◽  
Proton Transfer ◽  
Intermolecular Hydrogen Bond

scholarly journals Excited-state intramolecular proton transfer in a bioactive flavonoid provides fluorescence observables for recognizing its engagement with target proteins

2019 ◽  
Vol 18 (9) ◽  
pp. 2270-2280 ◽  
Author(s):  
Davide Vanossi ◽  
Monica Caselli ◽  
Giorgia Pavesi ◽  
Chiara Borsari ◽  
Pasquale Linciano ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Excited State ◽  
Proton Transfer ◽  
Bond Formation ◽  
Intermolecular Hydrogen Bond ◽  
Intramolecular Proton Transfer ◽  
Hydrogen Bond Formation ◽  
Target Proteins ◽  
Emission Properties

Intra- vs. intermolecular hydrogen-bond formation and ESIPT in a bioactive flavonoid result in different emission properties and provide a clue for recognizing its binding to target proteins.

scholarly journals Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1H-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 3802
Author(s):  
Dominik Kurzydłowski ◽  
Taisiia Chumak ◽  
Jakub Rogoża ◽  
Arkadiusz Listkowski
Keyword(s):  
Hydrogen Bond ◽  
Proton Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Molecular Crystals ◽  
Transfer Reactions ◽  
Hydrogen Bond Donor ◽  
Double Proton Transfer ◽  
Proton Transfer Reactions ◽  
Dft Modelling ◽  
Intramolecular Transfer

1H-pyrrolo[3,2-h]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H∙∙∙N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP).

The excited-state multiple proton transfer mechanism of the 7-hydroxyquinoline–(CH3OH)3cluster

2015 ◽  
Vol 39 (12) ◽  
pp. 9910-9917 ◽  
Author(s):  
Yanling Cui ◽  
Hong Zhao ◽  
Jinfeng Zhao ◽  
Pengyu Li ◽  
Peng Song ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Excited State ◽  
Proton Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Transfer Mechanism ◽  
Excited State Proton Transfer

Two proposed competitive types of multiple excited-state proton transfer take place along the intermolecular hydrogen-bond for 7-hydroxyquinoline–(CH3OH)3.

Theoretical study of the ground and excited states of 1-methylamideanthraquinone and its complex with fluoride anion

2016 ◽  
Vol 15 (04) ◽  
pp. 1650033
Author(s):  
Bing-Qiang Wang ◽  
Xiao-Fen Yin ◽  
Yan-Yun Dong ◽  
Cai-Yun Zhang
Keyword(s):  
Density Functional Theory ◽  
Hydrogen Bond ◽  
Proton Transfer ◽  
Density Functional ◽  
Intermolecular Hydrogen Bond ◽  
Emission Spectra ◽  
Intramolecular Proton Transfer ◽  
Fluoride Anion ◽  
Functional Theory ◽  
Intramolecular Hydrogen

We have performed a series of calculations using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) for 1-methylamideanthraquinone (MAAQ). In the S0 state of MAAQ, amide group is coplanar with anthraquinone, and an intramolecular hydrogen bond [Formula: see text] is formed. The [Formula: see text] transition has an intramolecular charge transfer character. Two stable structures (planar nMAAQ and twisted tMAAQ) have been obtained in the S1 state of MAAQ. Thereinto, nMAAQ is lower by 0.105[Formula: see text]eV than tMAAQ in energy, so nMAAQ is the dominant conformation in the S1 state of MAAQ and the emission spectra of tMAAQ cannot be observed in the solution of MAAQ. Excited state intramolecular proton transfer (ESIPT) between C[Formula: see text]O and N–H was not observed in the S1 state of MAAQ. Upon addition of fluoride anion, only twisted conformations were obtained in both S0 and S1 states of MAAQ-F[Formula: see text]. An intermolecular hydrogen bond [Formula: see text] is formed in the S0 state, and intermolecular proton transfer happens in the S1 state for MAAQ-F[Formula: see text].

X-Ray crystallographic and spectroscopic properties of eight Schiff bases as evidence of the proton transfer reaction. Role of the intermolecular hydrogen bond

2011 ◽  
Vol 35 (1) ◽  
pp. 156-164 ◽  
Author(s):  
Oscar Domínguez ◽  
Braulio Rodríguez-Molina ◽  
Mario Rodríguez ◽  
Armando Ariza ◽  
Norberto Farfán ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Proton Transfer ◽  
Schiff Bases ◽  
Transfer Reaction ◽  
Intermolecular Hydrogen Bond ◽  
Spectroscopic Properties ◽  
Proton Transfer Reaction ◽  
X Ray

The effect of benzo-annelation on intermolecular hydrogen bond and proton transfer of 2-methyl-3-hydroxy-4(1H)-quinolone in methanol: A TD-DFT study

2018 ◽  
Vol 31 (5) ◽  
pp. e3803 ◽  
Author(s):  
Yanliang Zhao ◽  
Meishan Wang ◽  
Panwang Zhou ◽  
Chuanlu Yang ◽  
Xiaoguang Ma ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Proton Transfer ◽  
Intermolecular Hydrogen Bond ◽  
Dft Study ◽  
Td Dft

Synthesis and characterization of photothermal antibacterial hydrogel with enhanced mechanical properties

2021 ◽  
Author(s):  
Shu bin Li ◽  
Xiao Wang ◽  
Jiang Zhu ◽  
Zhenyu Wang ◽  
Lu Wang
Keyword(s):  
Mechanical Properties ◽  
Hydrogen Bond ◽  
Fe3o4 Nanoparticles ◽  
Intermolecular Hydrogen Bond ◽  
Amide Bond ◽  
Synthesis And Characterization

In this work, using carboxyl-modified Fe3O4 nanoparticles as a photothermal agent, combining the chemical amide bond and intermolecular hydrogen bond crosslinking force, a photothermal hydrogel with enhanced mechanical properties was...

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