Synthesis and characterization of tailor-made o-hydroxysubstituted anils through <sup>1</sup>H NMR, ­<sup>13</sup>C NMR, SC-XRD and DFT studies for possible optoelectronic applications

Biswal, Supriya Priyambada; Hota, Prabhudatta; Dash, Manas Ranjan; Mahapatra, Ambikesh; Misra, Pratibha

doi:10.1080/00268976.2023.2225651

Cited by 3 publications

(2 citation statements)

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“…The 6-311(d,p) basis set has emerged as a highly cost-efficient choice for accurately predicting a range of properties, including geometry optimization, thermochemical behaviour, crystal structures, spectroscopic analyses, and noncovalent interactions. Employing the B3LYP/6-311(d,p) level of theory has been shown to strike an optimal balance between minimal error margins and manageable computational demands, as is evident in [31,32]. Further validation of the DFT/B3LYP method, using the 6-311G++(d,p) basis set, was conducted by comparing the calculated bond lengths and angles with those reported in the literature [32,33].…”

Section: Computational Methodologymentioning

confidence: 99%

“…Employing the B3LYP/6-311(d,p) level of theory has been shown to strike an optimal balance between minimal error margins and manageable computational demands, as is evident in [31,32]. Further validation of the DFT/B3LYP method, using the 6-311G++(d,p) basis set, was conducted by comparing the calculated bond lengths and angles with those reported in the literature [32,33].…”

Section: Computational Methodologymentioning

confidence: 99%

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X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Lahmidi,

Bakheit,

Essassi

et al. 2023

Crystals

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This study investigated the crystallographic and electronic properties of 1,5-benzodiazepine compounds, namely: cis-(3S,4S)-3-hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 3b, trans-(3R,4R)-1-ethyl-3-hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one 4, and trans-(3S,4S) 1-ethyl-3-ethoxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 5. Hirshfeld surface analysis was also applied to discern the intermolecular interactions, highlighting the significance of hydrogen bonding, van der Waals forces, and the influence of specific substituents. Furthermore, the MESP maps created using the density functional theory revealed the electrostatic nature of these molecules. The absence of dark blue regions on the MESP maps and variations due to different functional groups and substitutions were noteworthy findings. Collectively, this research offers crucial insights into the behaviour, interactions, and potential applications of new compounds. Finally, the anticancer effects of compounds 3b, 4, and 5 were evaluated against three cancer cell lines and one normal cell line, and the results showed that 3b and 4 had potent antiproliferative effects against all three cancer cell lines.

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Section: Computational Methodologymentioning

confidence: 99%

Section: Computational Methodologymentioning

confidence: 99%

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Lahmidi,

Bakheit,

Essassi

et al. 2023

Crystals

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Combined Experimental and Theoretical Investigation of the Electrochemical Behavior of Hydroxy‐Substituted Anils

Priyambada Biswal,

Hota,

Ranjan Dash

et al. 2024

ChemistrySelect

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The present work explored the electrochemical behavior of two organic compounds, o‐hydroxybenzylidene‐orthochloroaniline(Anil‐1) and o‐hydroxynaphthalidene‐orthochloro aniline(Anil‐2) through a series of theoretical and experimental investigations. The vibrational frequencies of two anilswere analyzed experimentally by FTIR and theoretically by DFT studies. A comparison of the frequencies with their unsubstituted analog, o‐hydroxybenzylideneaniline, confirmed the electron‐donating nature of the −Cl and −OH substituents in anils. The hyperconjugative interaction energy obtained from NBO analysis divulged the direction of the electron donation from the donor orbitals to the acceptor orbitals. UV‐visible studies illustrated prominent π→π* electronic transitions with significant oscillator strength(0.10–0.26) and molar extinction coefficient(~104) experimentally. Analysis of the global and local reactive descriptors of anils revealed a lower HOMO‐LUMO energy gap of Anil‐2(4.05 eV) than Anil‐1(4.46 eV), corroborating the order of decreasing reactivity to be Anil‐2>Anil‐1. The Cyclic Voltammetry studies disclosed the involvement of an oxidation process in Anil‐1 and Anil‐2 with a higher oxidation potential of Anil‐1 (1.43 V) than Anil‐2(1.31 V) due to the naphthyl moiety of the latter. However, the absence of a cathodic peak in both cases envisaged the irreversible nature of oxidation. The results demonstrated that both the anils could be suitable optical materials for microelectronics applications.

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Theoretical interpretation of electron delocalization potential of the substituent in o-hydroxynaphthalidene-p-substituted anilines for prospective molecular electronics applications

Biswal,

Hota,

Dash

et al. 2024

Discov Mol

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Synthesis and characterization of tailor-made o-hydroxysubstituted anils through ¹H NMR, ¹³C NMR, SC-XRD and DFT studies for possible optoelectronic applications

Cited by 3 publications

References 74 publications

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Combined Experimental and Theoretical Investigation of the Electrochemical Behavior of Hydroxy‐Substituted Anils

Theoretical interpretation of electron delocalization potential of the substituent in o-hydroxynaphthalidene-p-substituted anilines for prospective molecular electronics applications

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Synthesis and characterization of tailor-made o-hydroxysubstituted anils through 1H NMR, ­13C NMR, SC-XRD and DFT studies for possible optoelectronic applications

Cited by 3 publications

References 74 publications

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Combined Experimental and Theoretical Investigation of the Electrochemical Behavior of Hydroxy‐Substituted Anils

Theoretical interpretation of electron delocalization potential of the substituent in o-hydroxynaphthalidene-p-substituted anilines for prospective molecular electronics applications

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Synthesis and characterization of tailor-made o-hydroxysubstituted anils through ¹H NMR, ¹³C NMR, SC-XRD and DFT studies for possible optoelectronic applications