FT-Raman and infrared spectra and vibrational assignments for 3-chloro-4-methoxybenzaldehyde, as supported by ab initio, hybrid density functional theory and normal coordinate calculations

Hiremath, Chidanandayya S.; Yenagi, Jayashree; Tonannavar, J.

doi:10.1016/j.saa.2006.12.050

Cited by 49 publications

(11 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The two conformers (shown in Figure 1) differ by the orientation of the methyl fragment (in the methoxy group) with respect to the oxygen atom of the aldehyde group. 25 In agreement with the previously reported microwave studies, 9,10 our calculations predict that the two conformers (both of C s symmetry) are almost isoenergetic. The O-trans form is computed to be more stable than the O-cis form by only 0.57 (MP2) or 0.17 (DFT) kJ mol -1 (E ZPE , see Table S4 of the Supporting Information).…”

Section: Resultssupporting

confidence: 92%

Thermal and Photoinduced Control of Relative Populations of 4-Methoxybenzaldehyde (p-Anisaldehyde) Conformers

Kuş¹,

Sharma²,

Reva³

et al. 2010

J. Phys. Chem. A

View full text Add to dashboard Cite

Two almost isoenergetic conformers of 4-methoxybenzaldehyde (p-anisaldehyde), O-trans and O-cis, are nearly equally populated in gas phase at room temperature. The existence of these two conformers of similar energy makes p-anisaldehyde an attractive molecule for conformational investigations, in which the relative populations of the two forms might be subjected to optical control. In the present study, monomers of the compound were trapped from the room-temperature gas phase into cryogenic argon and xenon matrices. The initial relative amount of the two conformers present in the freshly deposited matrices is shifted slightly in favor of the O-trans conformer. The ratio of the two forms could be reversibly varied by irradiating the sample with UV light in different wavelength ranges or by using the temperature variation. Increasing the temperature of the xenon matrix up to ca. 57 K led to conversion of the less stable O-cis form into the O-trans conformer, shifting the O-cis/O-trans ratio to ca. 1:7. A series of UV irradiations with different long-pass cutoff filters was carried out. UV excitation induced transformation of O-cis and O-trans conformers into each other. These transformations were leading to the UV-wavelength-specific photostationary equilibria characterized by the O-cis/O-trans ratios of about 1:2.2, 1:1.4, 1:1.1, and 1:0.89 for λ > 328, 295, 288, and 234 nm cutoff filters, respectively. The isomerization processes were probed by infrared spectroscopy and supported by quantum chemical calculations. The absorption bands observed in the infrared spectra of p-anisaldehyde isolated in argon and xenon matrices were assigned to the theoretically predicted normal modes.

show abstract

Section: Resultssupporting

confidence: 92%

Thermal and Photoinduced Control of Relative Populations of 4-Methoxybenzaldehyde (p-Anisaldehyde) Conformers

Kuş¹,

Sharma²,

Reva³

et al. 2010

J. Phys. Chem. A

View full text Add to dashboard Cite

show abstract

“…For 4CLPBIC, the CCl stretching vibrations are scaled at 455 cm −1 and the experimental FT‐IR signal occurred at 471 cm −1 and in FT‐Raman, the same mode occurred at 457 cm −1 . These vibrations show an exact correlation with the similar reported values [65–67].…”

Section: Resultssupporting

confidence: 90%

Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Murugavel

Jayakumar

Chandrasekaran

et al. 2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The N‐phenylbenzo[g]indazole derivatives, 3‐(4‐chlorophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (4CLPBIC), 3‐(4‐bromophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (4BRPBIC), and 3‐(3‐bromophenyl)‐3,3a,4,5‐tetrahydro‐N‐phenylbenzo[g]indazole‐2‐carbothioamide (3BRPBIC), were synthesized by the one‐pot green amalgamation of solvent‐free granulating methodology procedure at room temperature. The synthesized crystals were characterized by single‐crystal X‐ray diffraction (SC‐XRD), FT‐IR, FT‐Raman, NMR, and UV–Vis techniques. The molecular geometries from XRD experimental values of synthesized compounds 4CLPBIC, 4BRPBIC, and 3BRPBIC in the ground state are compared theoretically by applying the density functional theory (DFT), a method with the B3LYP/6‐311G(d,p) basis set using Gaussian 09 software. The vibrational assignments of the synthesized compounds were studied based on potential energy distribution (PED) by the VEDA4 program. The scaled DFT/B3LYP/6‐311G(d,p) results show the best agreement with the experimental values. Computational 1H and 13C NMR were acquired by utilizing gauge‐independent atomic orbital (GIAO) procedure, and chemical shift results are in good agreement with the experimental values. A web‐based theoretical investigation was performed to understand the drug‐likeness and ADMET properties of the compounds. Molecular docking studies were carried out against bacterial cholesterol inhibitor block and inhibitor of lanosterol‐14α‐demethylase CYP51 used in the treatment of topical and systemic mycoses in fungal to understand the inhibitory activity of synthesized compounds. The synthesized molecules were also tested for antibacterial and antifungal activities.

show abstract

“…The vibrations belonging to C-X (X = F, Cl, Br) bonds which are formed between the ring and the halogen atoms, are interesting since mixing of vibrations are possible due to the lowering of molecular symmetry and the presence of heavy atoms [32][33][34][35][36]. In FT-IR spectrum of 2ClT, a strong band at 680 cm −1 is assigned to C-Cl stretching vibration.…”

Section: C-cl Vibrationsmentioning

confidence: 99%

Vibrational spectroscopic analysis of 2-chlorotoluene and 2-bromotoluene: A combined experimental and theoretical study

Govindarajan¹,

Ganasan²,

Periandy³

et al. 2010

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

View full text Add to dashboard Cite

FT-Raman and infrared spectra and vibrational assignments for 3-chloro-4-methoxybenzaldehyde, as supported by ab initio, hybrid density functional theory and normal coordinate calculations

Cited by 49 publications

References 22 publications

Thermal and Photoinduced Control of Relative Populations of 4-Methoxybenzaldehyde (p-Anisaldehyde) Conformers

Thermal and Photoinduced Control of Relative Populations of 4-Methoxybenzaldehyde (p-Anisaldehyde) Conformers

Synthesis, spectral, crystal structure, drug‐likeness, in silico, and in vitro biological screening of halogen [Cl, Br] substituted N‐phenylbenzo[g]indazole derivatives as antimicrobial agents

Vibrational spectroscopic analysis of 2-chlorotoluene and 2-bromotoluene: A combined experimental and theoretical study

Contact Info

Product

Resources

About