Russian Journal of Physical Chemistry A, volume 94, issue 5, pages 925-932
Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond
Publication type: Journal Article
Publication date: 2020-05-07
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor: 0.7
ISSN: 00360244, 1531863X
Physical and Theoretical Chemistry
Abstract
Abstract Model molecular systems structurally similar to the transition state of the limiting step of the hydrolysis of cephalosporin antibiotics by the L1 metallo-β-lactamase are studied. The series of fluorinated compounds show that the nature of substituents in thiazine and β-lactam rings have a great impact on the strength of the intramolecular O–H···N hydrogen bond that determines the catalytic parameters in real biological systems. The strengthening or weakening of the O–H···N bond is registered via a quantum topological analysis of the electron density, supplemented with various bonding descriptors’ study. The obtained data are confirmed by the analysis of the vibrational frequency shift relatively to the nonfluorinated compound for the O‒H stretching mode of the carboxylic group involved in the O–H···N bond formation. The absence of the monotonic dependence of the hydrogen bond strength on the donor-acceptor effects of substituents shows that considered bonding descriptors do not provide a complete understanding of the bonding mechanisms in the active center of L1 metallo-β-lactamase.
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Journal of Structural Chemistry
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Journal of Structural Chemistry
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Pleiades Publishing
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Pleiades Publishing
1 publication, 100%
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Levina E. O. et al. Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond // Russian Journal of Physical Chemistry A. 2020. Vol. 94. No. 5. pp. 925-932.
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Levina E. O., Khrenova M. G., Tsirelson V. G. Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond // Russian Journal of Physical Chemistry A. 2020. Vol. 94. No. 5. pp. 925-932.
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TY - JOUR
DO - 10.1134/S0036024420050131
UR - https://doi.org/10.1134%2FS0036024420050131
TI - Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond
T2 - Russian Journal of Physical Chemistry A
AU - Levina, E O
AU - Khrenova, M. G.
AU - Tsirelson, V. G.
PY - 2020
DA - 2020/05/07 00:00:00
PB - Pleiades Publishing
SP - 925-932
IS - 5
VL - 94
SN - 0036-0244
SN - 1531-863X
ER -
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@article{2020_Levina,
author = {E O Levina and M. G. Khrenova and V. G. Tsirelson},
title = {Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond},
journal = {Russian Journal of Physical Chemistry A},
year = {2020},
volume = {94},
publisher = {Pleiades Publishing},
month = {may},
url = {https://doi.org/10.1134%2FS0036024420050131},
number = {5},
pages = {925--932},
doi = {10.1134/S0036024420050131}
}
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Levina, E. O., et al. “Effect of Substituents in Hydrolyzed Cephalosporins on Intramolecular O–H···N Bond.” Russian Journal of Physical Chemistry A, vol. 94, no. 5, May. 2020, pp. 925-932. https://doi.org/10.1134%2FS0036024420050131.
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