TY - JOUR

T1 - Salen: Insight into the Crystal Structure, Hirshfeld Surface Analysis, Optical Properties, DFT, and Molecular Docking Studies

AU - Babashkina, Maria

AU - Panova, Elizaveta

AU - Alkhimova, Larisa

AU - Safin, Damir

N1 - This work was supported by state assignment of the Ministry of Science and Higher Education of the Russian Federation (Project Reg. No. 720000Ф.99.1.БЗ85АА13000). This work was partially performed using resources of the Research Resource Center "Natural Resource Management and Physico-Chemical Research".

PY - 2023

Y1 - 2023

N2 - We report on a known Schiff base dye salen. The crystal structure of salen is in the enol-enol tautomer. Molecules are packed into a 3D supramolecular framework through C-H center dot center dot center dot pi interactions. The absorption spectrum of salen in CH2Cl2 exhibits three bands in the UV region, while the spectrum in MeOH contains an additional band at 403 nm and a shoulder at 280 nm, corresponding to the cis-keto tautomer. The emission spectrum of salen in MeOH exhibits a band at 435 and 457 nm upon irradiation at 280 and 400 nm, respectively, arising from the enol-cis-keto* and/or cis-keto-cis-keto* tautomers. The solution of salen in CH2Cl2 showed dual emission with the bands at 349 and 462 nm upon irradiation at 290 nm with the low-energy emission band arising from the enol-cis-keto* and/or cis-keto-cis-keto* tautomers, while the high-energy band corresponds to the enol-enol* tautomer. The emission spectrum of salen in CH2Cl2 exhibits a single band at 464 nm upon irradiation at 380 nm, arising from the different conformers of the enol-cis-keto* and/or cis-keto-cis-keto* tautomers. The DFT calculations revealed that the enol-enol tautomer is the most favorable, followed by the enol-cis-keto tautomer. The global chemical reactivity descriptors were estimated from the HOMO and LUMO. The DFT calculations were also applied to probe salen as a potential corrosion inhibitor for some important metals used in implants. The enol-cis-keto and enol-trans-keto tautomers exhibit the best electron charge transfer from the molecule to the surface of all the studied metals, of which the most efficient electron charge transfer was established for Ni, Au, and Co. Molecular docking was applied to study interaction of tautomers of salen with a series of the SARS-CoV-2 proteins, of which the best binding affinity was found toward nsp14 (N7-MTase).

AB - We report on a known Schiff base dye salen. The crystal structure of salen is in the enol-enol tautomer. Molecules are packed into a 3D supramolecular framework through C-H center dot center dot center dot pi interactions. The absorption spectrum of salen in CH2Cl2 exhibits three bands in the UV region, while the spectrum in MeOH contains an additional band at 403 nm and a shoulder at 280 nm, corresponding to the cis-keto tautomer. The emission spectrum of salen in MeOH exhibits a band at 435 and 457 nm upon irradiation at 280 and 400 nm, respectively, arising from the enol-cis-keto* and/or cis-keto-cis-keto* tautomers. The solution of salen in CH2Cl2 showed dual emission with the bands at 349 and 462 nm upon irradiation at 290 nm with the low-energy emission band arising from the enol-cis-keto* and/or cis-keto-cis-keto* tautomers, while the high-energy band corresponds to the enol-enol* tautomer. The emission spectrum of salen in CH2Cl2 exhibits a single band at 464 nm upon irradiation at 380 nm, arising from the different conformers of the enol-cis-keto* and/or cis-keto-cis-keto* tautomers. The DFT calculations revealed that the enol-enol tautomer is the most favorable, followed by the enol-cis-keto tautomer. The global chemical reactivity descriptors were estimated from the HOMO and LUMO. The DFT calculations were also applied to probe salen as a potential corrosion inhibitor for some important metals used in implants. The enol-cis-keto and enol-trans-keto tautomers exhibit the best electron charge transfer from the molecule to the surface of all the studied metals, of which the most efficient electron charge transfer was established for Ni, Au, and Co. Molecular docking was applied to study interaction of tautomers of salen with a series of the SARS-CoV-2 proteins, of which the best binding affinity was found toward nsp14 (N7-MTase).

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000828949800001

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85134690675

U2 - 10.1080/10406638.2022.2097281

DO - 10.1080/10406638.2022.2097281

M3 - Article

VL - 43

SP - 5116

EP - 5138

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

SN - 1040-6638

IS - 6

ER -