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Phenols
Published in Brian D. Fath, Sven E. Jørgensen, Megan Cole, Managing Global Resources and Universal Processes, 2020
Leszek Wachowski, Robert Pietrzak
According to the IUPAC nomenclature, in naming substitution products of these compounds, the numbering starts at the group already present and is done in the direction that gives the lowest numbers to other groups on the ring. Sometimes, the benzene ring is treated as a substituent (for hydrogen) on another molecule. In that case, the C6H5- group of benzene is called “phenyl.” Substituents are cited in alphabetical order. Carboxyl and acyl groups take precedence over the phenolic hydroxyl in determining the base name. The hydroxyl group is treated as a substituent. Higher substituted compounds are named as derivatives of phenol.
Organic Pollutants
Published in Paul Mac Berthouex, Linfield C. Brown, Chemical Processes for Pollution Prevention and Control, 2017
Paul Mac Berthouex, Linfield C. Brown
Phenol, also known as carbolic acid, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. A phenyl group (–C6H5) is a benzene molecule with one hydrogen atom removed. The phenol molecule is a phenyl group (–C6H5) bonded to a hydroxyl group (–OH). It is mildly acidic and it has a propensity to cause chemical burns.
N-Heterocyclic carbene complexes of Au(I), Ag(I), and Cu(I) as potential anticancer agents: a review
Published in Journal of Coordination Chemistry, 2023
All the complexes exhibited good activities against the tested cancer cells. M-NHC95 containing N-phenyl substituent was the most potent compound. The presence of the phenyl group is likely to exert a stabilizing effect on the Ag(I)–NHC bond, causing silver to be released slowly and enhancing cytotoxic activity. The introduction of an OH group to the backbone of the ligand enhances cytotoxic activity, probably due to the solubility of M-NHC96, and its ability to cross the cell membrane [75]. Asif et al. synthesized two new Ag(I)–NHC complexes (M-NHC97 and M-NHC98, Figure 7) having lypophilic terminal octyl and decyl chains. Both complexes were screened for their cytotoxic activities against human cancer and normal cell lines by using MTT assay; M-NHC98 was selectively toxic toward HCT 116 cell lines. The mechanism of action of M-NHC98 was also investigated. M-NHC98 has excellent anti-metastatic and pro-apoptotic activities against HCT 116 cancer cell lines [76]. Haque et al. prepared three NHC-based Ag(I) complexes (M-NHC99-M-NHC101) characterized by FT-IR, 1H and 13C NMR, and elemental analysis. The anticancer activities were evaluated against HT29 and HCT 116 cancer cell lines. All the complexes showed excellent anticancer activities with very low IC50 values [77].
Dioxido-vanadium(V) complex catalyzed oxidation of alcohols and tandem synthesis of oximes: a simple catalytic protocol for C–N bond formation
Published in Journal of Coordination Chemistry, 2021
Using the above method for oxidation of alcohols, hydroxylamine was added in molar ratio to the solution containing 1, benzyl alcohol and 15% hydrogen peroxide under stirring. The completion of the reaction was monitored using thin layer chromatography and the yield of oxime was confirmed by 1H and 13C NMR spectroscopy. The catalytic studies were tested using benzyl alcohol as the probe substrate and after 3 h the desired benzaldehyde oxime 2a was formed in 80% yield (Table 4). Similarly, the conversion of p-nitro benzyl alcohol and p-methoxy benzyl alcohol to corresponding products p-nitro benzaldehyde oxime 2b was 87% yield and p-methoxy benzaldehyde oxime 2c was 75% yield, lower compared to p-nitro benzaldehyde oxime. This can be attributed to the substituent effect on the phenyl ring. Hence, electron withdrawing enhances the yield of the product whereas the electron-donating group decreases the yield of the product. Other substrates such as 2-pyridine methanol and o-methyl benzyl alcohol were also tested giving the corresponding products, 81% yield of picolinaldehyde oxime and 78% yield of o-methyl benzaldehyde oxime.
Excited-state dynamics of isolated and (micro)solvated methyl sinapate: the bright and shady sides of a natural sunscreen
Published in Molecular Physics, 2021
Jiayun Fan, Wim Roeterdink, Wybren Jan Buma
An important class of compounds that are used both as natural as well as artificial UV-B protectants are based on cinnamic acid and its derivatives. Plants employ sinapate esters featuring methoxy substituents meta to the vinyl group and a para hydroxy group, while commercial sunscreens use alkyl-esters with only a p-methoxy substituent on the phenyl ring. Although these compounds have been known for a long time, high-resolution laser spectroscopic studies on 2-ethylhexyl-4-methoxycinnamate (EHMC) -the most common UV-B filter found in commercial sunscreens- led to the realisation that high-resolution studies in the frequency domain and time-resolved studies in the time domain can contribute significantly to the development of novel sunscreens [15–17]. As a result, recent years have witnessed a rapidly increasing interest in the detailed understanding of the spectroscopic properties of the electronically excited states of these compounds and their dynamics, and how to employ this knowledge to design and develop UV filters with improved properties [18–33].