Synthesis, spectral and theoretical (DFT) investigations of 4,6-diphenyl-6-hydroxy-1-{[(1Z)-1-phenyl ethylidene] amino}tetrahydropyrimidine-2(1H)-one

Arı, Hatice; Özpozan, Talat; Büyükmumcu, Zeki; Akın, Nazenin

doi:10.1016/j.molstruc.2021.131820

Cited by 3 publications

(3 citation statements)

References 71 publications

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“…All calculations were performed using Gaussian 09 22 and Gaussian 16. 23 The vibrational wavenumbers calculated by the B3LYP and CAM-B3LYP methods were calibrated with scaling factors of 0.9613 24 and 0.9497, 25 respectively. The bonding characteristics of S-DR3 were investigated by monitoring IR spectral changes upon the photo-induced formation of S-DR3 from its precursor azo compound (AZ3s).…”

Section: Experimental and Theoretical Methodsmentioning

confidence: 99%

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Substituted effects on bonding characteristics of cyclopentane‐1,3‐diyl diradicals monitored by time‐resolved infrared spectroscopy

Kondoh,

Kuboki,

Kume

et al. 2023

J of Physical Organic Chem

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Cyclopentane‐1,3‐diyl diradicals (DRs) provide excellent opportunities to study the properties of diradicals because their lifetimes can be significantly lengthened to up to milliseconds with the introduction of proper substituents. This study investigated the bonding characteristics of singlet and triplet DRs having C=O and p‐cyanophenyl groups (S‐DR3 and T‐DR3) by monitoring the photo‐induced formation of the diradicals from their precursor azo compounds using time‐resolved IR (TR‐IR) spectroscopy. Upon the formation of S‐DR3, a C=O stretching wavenumber was upshifted by 22 cm−1, whereas a C≡N stretching one was downshifted by 12 cm−1. The observed shifts indicate that the unpaired electrons increase and decrease the C=O and C≡N bond orders, respectively. The effects of the unpaired electrons in S‐DR3 were similar to those observed in our previous TR‐IR studies on a singlet cyclopentane‐1,3‐diyl diradical having C=O but no C≡N groups (S‐DR2) and on that having C≡N but no C=O groups (S‐DR1), respectively. Contrastingly, upon the formation of T‐DR3, the C=O wavenumber was downshifted by 16 cm−1, indicating that the unpaired electrons decrease the C=O bond order. More notably, no detectable shifts were observed in the C≡N stretching wavenumber. These observations are not clearly explained by a model suggested in the previous studies on S‐DRs. Here, we discuss and propose a more elaborated resonance hybrid of DRs that can explain the directions and relative magnitudes of the observed wavenumber shifts irrespective of spin multiplicities. We expect that the findings and suggestions presented here will stimulate research in both organic and theoretical chemistry.

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Section: Experimental and Theoretical Methodsmentioning

confidence: 99%

“…All calculations were performed using Gaussian 09 22 and Gaussian 16 23 . The vibrational wavenumbers calculated by the B3LYP and CAM‐B3LYP methods were calibrated with scaling factors of 0.9613 24 and 0.9497, 25 respectively.…”

Section: Experimental and Theoretical Methodsmentioning

confidence: 99%

Substituted effects on bonding characteristics of cyclopentane‐1,3‐diyl diradicals monitored by time‐resolved infrared spectroscopy

Kondoh,

Kuboki,

Kume

et al. 2023

J of Physical Organic Chem

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“…The new scaling factors 0.9617 and 0.9531 for B3LYP/6-31G(d) and M06-2X/6-31G(d) were obtained by minimizing relative error values, respectively. The scale factor calculations were previously made for these methods by other groups, and the values are given as 0.9613 [31], 0.9614 [32,33] for B3LYP/6-31G(d) and 0.9496 [34], 0.9463 [35] for M06-2X/6-31G(d), respectively.…”

Section: Vibrational Characterizationmentioning

confidence: 99%

DFT Calculations in Monomeric and Dimeric Forms of N-Benzylmaleimide (Nbm) Combined With Vibrational Spectroscopic Parameters

Arı

2023

Eskişehir Teknik Üniversitesi Bilim Ve Teknoloji Dergisi B - Teorik Bilimler

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The structural, vibrational and theoretical analyses of N-benzylmaleimide (NBM) having chemical and biological significances have been made. The four possible conformers and their sixty-six dimeric forms linked by the intermolecular C=O···H hydrogen bonding were investigated for the stability. The conformational and the dimeric structures of NBM in the gas phase were investigated and the population distributions of the conformations and dimers were obtained using the Boltzmann distribution. The experimental IR and Raman spectra of solid phase NBM were recorded, and the bands were compared with the theoretical wavenumber the values of the monomer and the dimer forms for their assignments. The new scale factors (0.9617 for B3LYP/6-31G(d) and 0.9531 for M06-2X/6-31G(d)) obtained for NBM can be used more accurately in vibration calculations of all maleimide derivatives. The Molecular Electrostatic Potential (MEP) map showed that the negative and the positive regions have changed from monomeric to dimeric form changes, while the HOMO-LUMO shapes did not generally change in monomeric and dimeric forms. The nucleophilic and electrophilic Fukui functions and dual descriptors shows that maleimide and benzyl groups are nucleophilic and electrophilic regions, respectively, additionally the dual descriptor values decrease upon dimerization.

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Vibrational (FT-IR), electronic (UV-Vis), thermodynamic, and NBO analyses of amide ↔ imide forms of articaine: a computational perspective on prototropic tautomerism

Serin,

Doğan Ulu

2023

Molecular Physics

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Synthesis, spectral and theoretical (DFT) investigations of 4,6-diphenyl-6-hydroxy-1-{[(1Z)-1-phenyl ethylidene] amino}tetrahydropyrimidine-2(1H)-one

Cited by 3 publications

References 71 publications

Substituted effects on bonding characteristics of cyclopentane‐1,3‐diyl diradicals monitored by time‐resolved infrared spectroscopy

Substituted effects on bonding characteristics of cyclopentane‐1,3‐diyl diradicals monitored by time‐resolved infrared spectroscopy

DFT Calculations in Monomeric and Dimeric Forms of N-Benzylmaleimide (Nbm) Combined With Vibrational Spectroscopic Parameters

Vibrational (FT-IR), electronic (UV-Vis), thermodynamic, and NBO analyses of amide ↔ imide forms of articaine: a computational perspective on prototropic tautomerism

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