Conformational and vibrational analysis of S-(2-methoxyphenyl)-4-substituted-benzenecarbothioates, using X-ray, infrared and Raman spectroscopy and theoretical calculations

Castañeda, Isabel C. Henao; Jios, Jorge L.; Piro, Oscar E.; Tobón, G.; Védova, Carlos O. Della

doi:10.1016/j.molstruc.2006.12.007

Cited by 15 publications

(5 citation statements)

References 9 publications

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“…(The “g” and “u” symmetry labels appropriate for D 4 h molecular symmetry are retained, even though the NiPc(OBu) 8 macrocycle is distinctly saddled due to steric crowding of the butoxy substituents. , ) Except for the 1470 cm –1 band, assigned to the totally symmetric mode, ν 3 , the measured depolarization ratios are all close to 0.75, indicating B 1g or B 2g modes. One band, 1278 cm –1 , does not have a correspondence in the CuPc spectrum and is suggested to arise from a mode involving the ring-O stretch of the butoxy substituents; the ring-O stretch of phenoxy compounds is commonly found in this region. − …”

Section: Resultssupporting

confidence: 86%

Ultrafast Charge Transfer in Nickel Phthalocyanine Probed by Femtosecond Raman-Induced Kerr Effect Spectroscopy

et al. 2014

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The recently developed technique of femtosecond stimulated Raman spectroscopy, and its variant, femtosecond Raman-induced Kerr effect spectroscopy (FRIKES), offer access to ultrafast excited-state dynamics via structurally specific vibrational spectra. We have used FRIKES to study the photoexcitation dynamics of nickel(II) phthalocyanine with eight butoxy substituents, NiPc(OBu)8. NiPc(OBu)8 is reported to have a relatively long-lived ligand-to-metal charge-transfer (LMCT) state, an essential characteristic for efficient electron transfer in photocatalysis. Following photoexcitation, vibrational transitions in the FRIKES spectra, assignable to phthalocyanine ring modes, evolve on the femtosecond to picosecond time scales. Correlation of ring core size with the frequency of the ν10 (asymmetric C–N stretching) mode confirms the identity of the LMCT state, which has a ∼500 ps lifetime, as well as that of a precursor d-d excited state. An even earlier (∼0.2 ps) transient is observed and tentatively assigned to a higher-lying Jahn–Teller-active LMCT state. This study illustrates the power of FRIKES spectroscopy in elucidating ultrafast molecular dynamics.

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Section: Resultssupporting

confidence: 86%

Ultrafast Charge Transfer in Nickel Phthalocyanine Probed by Femtosecond Raman-Induced Kerr Effect Spectroscopy

et al. 2014

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“…Thioester (X=S) and ester (X=O) moieties usually present a synperiplanar configuration around the δO=C-X-C dihedral angle as the more stable conformer. The results obtained for compounds I, II and III are in agreement with previous reports [11,16,17].…”

Section: Discussionsupporting

confidence: 92%

Synthetic Inhibitors of Snake Venom Enzymes: Thioesters Derived from 2-Sulfenyl Ethylacetate

2019

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Snakebite envenomings are a global public health issue. The therapy based on the administration of animal-derived antivenoms has limited efficacy against the venom-induced local tissue damage, which often leads to permanent disability. Therefore, there is a need to find inhibitors against toxins responsible for local damage. This work aimed to synthesize thioesters derived from 2-sulfenyl ethylacetate and to evaluate the inhibitory effects on two snake venom toxins. Ethyl 2-((4-chlorobenzoyl)thio)acetate (I), Ethyl 2-((3-nitrobenzoyl)thio)acetate (II) and Ethyl 2-((4-nitrobenzoyl)thio)acetate (III) were synthesized and spectroscopically characterized. Computational calculations were performed to support the study. The inhibitory capacity of compounds (I–III) was evaluated on a phospholipase A2 (Cdcum6) isolated from the venom of the Colombian rattlesnake Crotalus durissus cumanensis and the P-I type metalloproteinase Batx-I isolated from Bothrops atrox. I–III inhibited PLA2 with IC50 values of 193.2, 305.4 and 132.7 µM, respectively. Otherwise, compounds II and III inhibited the proteolytic activity of Batx-I with IC50 of 2774 and 1879 µM. Molecular docking studies show that inhibition of PLA2 may be due to interactions of the studied compounds with amino acids in the catalytic site and the cofactor Ca2+. Probably, a blockage of the hydrophobic channel and some amino acids of the interfacial binding surface of PLA2 may occur.

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“…Klimentova et al [42] reported the asymmetric and symmetric C-O-C stretching vibrations in the range, 1214-1097 cm À1 . Castaneda et al [43] reported the methoxy vibrations at 1252, 1190, 1172, 1028 and 1011 cm À1 theoretically.…”

Section: Ir and Raman Spectramentioning

confidence: 98%

Spectroscopic and theoretical characterization of 2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole 3-oxide

Benzon

Varghese

Panicker³

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Conformational and vibrational analysis of S-(2-methoxyphenyl)-4-substituted-benzenecarbothioates, using X-ray, infrared and Raman spectroscopy and theoretical calculations

Cited by 15 publications

References 9 publications

Ultrafast Charge Transfer in Nickel Phthalocyanine Probed by Femtosecond Raman-Induced Kerr Effect Spectroscopy

Ultrafast Charge Transfer in Nickel Phthalocyanine Probed by Femtosecond Raman-Induced Kerr Effect Spectroscopy

Synthetic Inhibitors of Snake Venom Enzymes: Thioesters Derived from 2-Sulfenyl Ethylacetate

Spectroscopic and theoretical characterization of 2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole 3-oxide

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