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

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).

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