NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

Andrei Gurinov; Gleb S. Denisov; Alexandra O. Borissova; Alexander S. Goloveshkin; Julian Greindl; Hans-Heinrich Limbach; Ilya G. Shenderovich

doi:10.1021/acs.jpca.7b09285

NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

Andrei Gurinov, Gleb S. Denisov, Alexandra O. Borissova, Alexander S. Goloveshkin, Julian Greindl, Hans-Heinrich Limbach, Ilya G. Shenderovich

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer's size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.

Original language	English (US)
Pages (from-to)	8697-8705
Number of pages	9
Journal	The Journal of Physical Chemistry A
Volume	121
Issue number	45
DOIs	https://doi.org/10.1021/acs.jpca.7b09285
State	Published - Nov 7 2017

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was supported by the German-Russian Interdisciplinary Science Center (G-RISC) funded by the German Federal Foreign Office via the German Academic Exchange Service (DAAD) and the Russian Foundation for Basic Research (Project 17-03-00590). We gratefully acknowledge the Gauss Centre for Supercomputing e.V. (www.gauss-centre.eu) for funding this project by providing computing time on the GCS Supercomputer SuperMUC at Leibniz Supercomputing Centre (LRZ, www.lrz.de)

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10.1021/acs.jpca.7b09285

https://repository.kaust.edu.sa/bitstream/10754/625972/1/acs.jpca.7b09285.pdf

Cite this

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title = "NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size",

abstract = "Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer's size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.",

author = "Andrei Gurinov and Denisov, {Gleb S.} and Borissova, {Alexandra O.} and Goloveshkin, {Alexander S.} and Julian Greindl and Hans-Heinrich Limbach and Shenderovich, {Ilya G.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the German-Russian Interdisciplinary Science Center (G-RISC) funded by the German Federal Foreign Office via the German Academic Exchange Service (DAAD) and the Russian Foundation for Basic Research (Project 17-03-00590). We gratefully acknowledge the Gauss Centre for Supercomputing e.V. (www.gauss-centre.eu) for funding this project by providing computing time on the GCS Supercomputer SuperMUC at Leibniz Supercomputing Centre (LRZ, www.lrz.de)",

year = "2017",

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doi = "10.1021/acs.jpca.7b09285",

language = "English (US)",

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journal = "The Journal of Physical Chemistry A",

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T1 - NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

AU - Gurinov, Andrei

AU - Denisov, Gleb S.

AU - Borissova, Alexandra O.

AU - Goloveshkin, Alexander S.

AU - Greindl, Julian

AU - Limbach, Hans-Heinrich

AU - Shenderovich, Ilya G.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the German-Russian Interdisciplinary Science Center (G-RISC) funded by the German Federal Foreign Office via the German Academic Exchange Service (DAAD) and the Russian Foundation for Basic Research (Project 17-03-00590). We gratefully acknowledge the Gauss Centre for Supercomputing e.V. (www.gauss-centre.eu) for funding this project by providing computing time on the GCS Supercomputer SuperMUC at Leibniz Supercomputing Centre (LRZ, www.lrz.de)

PY - 2017/11/7

Y1 - 2017/11/7

N2 - Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer's size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.

AB - Hydrogen bond geometries in the proton-bound homodimers of quinoline and acridine derivatives in an aprotic polar solution have been experimentally studied using 1H NMR at 120 K. The reported results show that increase of the dielec-tric permittivity of the medium results in contraction of the N…N distance. The degree of contraction depends on the homodimer's size and its substituent-specific solvation features. Neither of these effects can be reproduced using conven-tional implicit solvent models employed in computational studies. In general, the N…N distance in the homodimers of pyridine, quinoline, and acridine derivatives decreases in the sequence gas phase > solid state > polar solvent.

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UR - http://pubs.acs.org/doi/abs/10.1021/acs.jpca.7b09285

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DO - 10.1021/acs.jpca.7b09285

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SN - 1089-5639

VL - 121

SP - 8697

EP - 8705

JO - The Journal of Physical Chemistry A

JF - The Journal of Physical Chemistry A

IS - 45

ER -

NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

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CCDC 1552802: Experimental Crystal Structure Determination : acridinium acridine tetrakis[3,5-bis(trifluoromethyl)phenyl]borate chloroform solvate

CCDC 1552803: Experimental Crystal Structure Determination : acridinium acridine tetrakis[3,5-bis(trifluoromethyl)phenyl]borate toluene solvate

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NMR Study of Solvation Effect on Geometry of Proton-Bound Homodimers of Increasing Size

Abstract

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Datasets

CCDC 1552802: Experimental Crystal Structure Determination : acridinium acridine tetrakis[3,5-bis(trifluoromethyl)phenyl]borate chloroform solvate

CCDC 1552803: Experimental Crystal Structure Determination : acridinium acridine tetrakis[3,5-bis(trifluoromethyl)phenyl]borate toluene solvate

Cite this