Products distribution and contribution of (de)chlorination, hydroxylation and coupling reactions to 2,4-dichlorophenol removal in seven oxidation systems

Pan, Xiaoxue; Wei, Junyan; Zou, Mengting; Chen, Jing; Qu, Ruijuan; Wang, Zunyao

doi:10.1016/j.watres.2021.116916

Cited by 66 publications

(15 citation statements)

References 50 publications

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“…Following the interesting investigation of researchers in the field of organic compounds, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40] the present work covers thermodynamic and kinetic characteristics of 1s-27s and 1t-27t along with the first isolated silylenes, IIs and IIt (Schemes 1 and 2). Effects of one and two fused benzene, pyridine, phosphinine, pyrrole, phosphole, furan, and thiophene rings on the aromaticity, APT charge, and MEP graph along with reactivity of these Hammick type silylenes are investigated at DFT.…”

Section: Resultsmentioning

confidence: 99%

Substituent effects of fused Hammick silylenes via density functional theory survey

Heravi

Habibzadeh

Ebadi

et al. 2021

J of Physical Organic Chem

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We compared and contrasted the substituent effects on ΔΕ s-t (singlet-triplet energy difference), band gap (ΔΕ HOMO-LUMO ), aromaticity, atomic polar tensor (APT) charge distribution and reactivity of 54 singlet and triplet fused Hammick silylenes derived from silabenzopyridine-4-ylidene (1s-27s, and 1t-27t), and the synthesized dialkylsilylene by Kira, respectively. In this investigation we found the following: (1) The most and the least thermodynamic stability compared to Kira's silylene is demonstrated by fusion of two thiophene rings in para-position and two phosphole rings in ortho-position, respectively (ΔΕ s-t = 331.0 and 115.1 vs. 138.6 kJ/mol, respectively). ( 2) Although fusion of benzene, pyrrole, furan, thiophene, and phosphole ring kinetically stabilizes the corresponding silylenes, fusion of pyridine and phosphinine ring destabilizes their silylenes versus the isolated silylene's Kira (with the range of ΔE HOMO-LUMO from 312.8 to 410.2 vs. 351.7 kJ/mol). (3) The trend of substituent effects per number and size of rings is two five-membered rings > one five-membered rings > one six-membered rings > two six-membered rings. (4) Almost all cases, singlet Hammick silylenes reveal greater nucleophilicity, lesser electrophilicity, lower chemical potential, and greater global hardness than the scrutinized silylene by Kira. (5) We are waiting for experimental testing and verifications that place the heteroatom in the silapyridine's plane in a favorable spatial position to act not only as π electron donor but also acceptor of σ electron density.

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Section: Resultsmentioning

confidence: 99%

Substituent effects of fused Hammick silylenes via density functional theory survey

Heravi

Habibzadeh

Ebadi

et al. 2021

J of Physical Organic Chem

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“…58 In the present study, the abundance of ERE binding sites on both vasa and dnd promoters suggested that expression of aforementioned genes might be directly regulated by ESR2a. 4,25 Previous studies have reported xenoestrogen-altered promoter activity through the EREdependent mechanism, leading to gonadal damage. 59,60 Using a series of reporter plasmids containing different regions of the promoters, we demonstrated that a positive putative ERE motif might be present in the promoters of vasa and dnd, which satisfies the regulatory effects of 2,4-DCP.…”

Section: Discussionmentioning

confidence: 99%

2,4-Dichlorophenol Increases Primordial Germ Cell Numbers via ESR2a-Dependent Pathway in Zebrafish Larvae

Liu

et al. 2022

Environ. Sci. Technol.

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Previous studies have reported the feminizing effects of 2,4-dichlorophenol (2,4-DCP) on zebrafish (Danio rerio). However, the effect of 2,4-DCP on the number of primordial germ cells (PGCs), an indicator for early sex differentiation, remains elusive. In the present study, Tg (piwil1:egfp-UTR nanos3) zebrafish (GFP-labeled PGCs) were treated with 2,4-DCP (10, 20, and 40 μg/L) from 5 to 15 days postfertilization to explore the effect on PGC numbers and to elucidate associated molecular mechanisms. The results showed that 2,4-DCP exposure increased PGC numbers, as evidenced by larger GFP fluorescent areas, upregulated expressions of PGC marker genes (vasa and dnd), and raised the female ratio. Notably, the mRNA level of estrogen receptor 2a (esr2a) was also increased subsequently. Moreover, docking studies revealed stable 2,4-DCP interactions with ESR2a, speculating a role of ESR2a signaling pathway in 2,4-DCP toxicity. Furthermore, in esr2a knockout (esr2a –/–) zebrafish, the effects of 2,4-DCP were considerably minimized, proving the involvement of the ESR2a signaling pathway in the 2,4-DCP-mediated increase in PGC numbers. Dual-luciferase reporter gene assay and point mutation studies demonstrated that 2,4-DCP-stimulated promoter activity was mediated by estrogen response element (ERE) located in −686/–674 of the vasa promoter and −731/–719 of the dnd promoter. Overall, 2,4-DCP can potentially enhance the expression of vasa and dnd by binding to zebrafish ESR2a, thus leading to increased PGC numbers and subsequent female-biased sex differentiation.

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“…Finally, it should be noted that transition metal complexes play important roles in intermolecular 1,2-difunctionalization of alkenes and the synthesis of organic compounds. [32][33][34][35][36][37][38][39][40]…”

Section: Chloro-trifluoromethylthiolationmentioning

confidence: 99%

Recent advances in intermolecular 1,2-difunctionalization of alkenes involving trifluoromethylthiolation

et al. 2021

RSC Adv.

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Products distribution and contribution of (de)chlorination, hydroxylation and coupling reactions to 2,4-dichlorophenol removal in seven oxidation systems

Cited by 66 publications

References 50 publications

Substituent effects of fused Hammick silylenes via density functional theory survey

Substituent effects of fused Hammick silylenes via density functional theory survey

2,4-Dichlorophenol Increases Primordial Germ Cell Numbers via ESR2a-Dependent Pathway in Zebrafish Larvae

Recent advances in intermolecular 1,2-difunctionalization of alkenes involving trifluoromethylthiolation

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