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1.
Huan Jing Ke Xue ; 44(1): 66-74, 2023 Jan 08.
Artigo em Chinês | MEDLINE | ID: mdl-36635796

RESUMO

Based on the sounding data of VOCs in the lower troposphere (0-1000 m) in the northern suburb of Nanjing in the autumn of 2020, the vertical profile distribution, diurnal variation, and photochemical reactivity of VOCs in this area were analyzed. The results showed that the volume fraction of VOCs decreased with the increase in height (72.1×10-9±28.1×10-9-56.4×10-9±24.8×10-9). Alkanes at all heights accounted for the largest proportion (68%-75%), followed by aromatics (10%-12%), halohydrocarbons (10%-11%), alkenes (3%-7%), and acetylene (2%). The diurnal variation of the boundary layer had a great influence on the VOCs profile. The lower boundary layer in the morning and evening caused the volume fraction of VOCs to accumulate near the ground and lower in the upper layer. The vertical distribution of VOCs was more uniform in the afternoon. In the morning, the volume fraction proportion of alkenes (alkanes) with strong (weak) photochemical reactivity decreased (increased) with the increase in height, indicating that the photochemical aging of VOCs in the upper layer was significant. In the afternoon, the vertical distribution of VOCs volume fraction and OFP in the lower troposphere were more uniform. Affected by the surrounding air masses with different sources, the volume fraction and component proportion of VOCs at each height were significantly different. The alkanes in rural air masses were vertically evenly distributed, and the proportion increased gradually with the height. The vertical negative gradient of VOCs volume fraction in the urban air mass was the largest, the volume fraction of VOCs near the ground was high, and it was rich in aromatics. The proportion of aromatics increased with the increase in VOCs volume fraction between 200-400 m height of industrial air mass. The near-surface VOCs volume fraction of the highway traffic air mass was high, and alkanes accounted for the largest proportion.


Assuntos
Poluentes Atmosféricos , Ozônio , Compostos Orgânicos Voláteis , Poluentes Atmosféricos/análise , Compostos Orgânicos Voláteis/análise , Monitoramento Ambiental , Alcenos/análise , Alcanos/análise , China , Ozônio/análise
2.
Dalton Trans ; 52(4): 1030-1035, 2023 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-36602028

RESUMO

Methyltrioxorhenium(VII) (MTO) is a widely employed catalyst for metathesis, olefination, and most importantly, oxidation reactions. It is often preferred to other oxometal complexes due to its stability in air and higher efficiency. The seminal papers of K. B. Sharpless showed that when pyridine derivatives are used as co-catalysts, MTO-catalyzed olefin epoxidation with H2O2 as oxidant, a particularly useful reaction, is accelerated, with pyridine speeding up catalytic turnover and increasing the lifetime of MTO under the reaction conditions. In this paper, combined experimental and theoretical results show that the occurrence of σ-hole interactions in catalytic systems extends to MTO. Four crystalline adducts between MTO and aliphatic and heteroaromatic bases are obtained, and their X-ray analyses display short Re⋯N/O contacts opposite to both O-Re and C-Re covalent bonds with geometries consistent with σ-hole interactions. Computational analyses support the attractive nature of these close contacts and confirm that their features are typical of σ-hole interactions. The understanding of the nature of Re⋯N/O interactions may help to optimize the ligand-acceleration effect of pyridine in the epoxidation of olefins under MTO catalysis.


Assuntos
Peróxido de Hidrogênio , Compostos Organometálicos , Peróxido de Hidrogênio/química , Compostos Organometálicos/química , Catálise , Alcenos/química , Piridinas
3.
Molecules ; 28(2)2023 Jan 11.
Artigo em Inglês | MEDLINE | ID: mdl-36677791

RESUMO

Ligands play a critical role in promoting transition-metal-catalyzed C-H activation reactions. However, owing to high sensitivity of the reactivity of C-H activation to metal catalysts, the development of effective ligands has been a formidable challenge in the field. Rh(I)-catalyzed C-H cyclization of benzimidazoles with alkenes has been faced with low reactivity, often requiring very harsh conditions. To address this challenge, a phosphine oxide-enabled Rh(I)-Al bimetallic catalyst was developed for the reaction, significantly promoting the reactivity and allowing the reaction to run at 120 °C with up to 97% yield.


Assuntos
Óxidos , Ródio , Estrutura Molecular , Alcenos , Ciclização , Ligantes , Benzimidazóis , Catálise
4.
J Chem Phys ; 158(3): 034302, 2023 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-36681629

RESUMO

Criegee intermediates, formed from the ozonolysis of alkenes, are known to have a role in atmospheric chemistry, including the modulation of the oxidizing capacity of the troposphere. Although studies have been conducted since their discovery, the synthesis of these species in the laboratory has ushered in a new wave of investigations of these structures, both theoretically and experimentally. In some of these theoretical studies, high-order corrections for correlation energy are included to account for the mid multi-reference character found in these systems. Many of these studies include a focus on kinetics; therefore, the calculated energies should be accurate (<1 kcal/mol in error). In this research, we compute the enthalpies of formation for a small set of Criegee intermediates, including higher-order coupled cluster corrections for correlation energy up to coupled cluster with perturbative quintuple excitations. The enthalpies of formation for formaldehyde oxide, anti-acetaldehyde oxide, syn-acetaldehyde oxide, and acetone oxide are presented at 0 K as 26.5, 15.6, 12.2, and 0.1 kcal mol-1, respectively. Additionally, we do not recommend the coupled cluster with perturbative quadruple excitations [CCSDT(Q)] energy correction, as it is approximately twice as large as that of the coupled cluster with full quadruple excitations (CCSDTQ). Half of the CCSDT(Q) energy correction may be included as a reliable, cost-effective estimation of CCSDTQ energies for Criegee intermediates.


Assuntos
Acetaldeído , Acetona , Fenômenos Físicos , Alcenos , Óxidos
5.
Inorg Chem ; 62(2): 979-988, 2023 Jan 16.
Artigo em Inglês | MEDLINE | ID: mdl-36603128

RESUMO

Benzylic C(sp3)-H alkylation of tertiary anilines with alkenes by an anilido-oxazoline-ligated scandium alkyl catalyst was recently reported with C-H site selectivity and alkene-dependent regioselectivity. Revealing the mechanism and origin of selectivity is undoubtedly of great importance for understanding experimental observations and developing new reactions. Herein, density functional theory (DFT) calculations have been carried out on the model reaction of Sc-catalyzed benzylic C(sp3)-H alkylation of N,N-dimethyl-o-toluidine with allylbenzene. The reaction generally undergoes the generation of active species, alkene insertion, and protonation steps. The difference of the distortion energy of the aniline moiety in transition states, which is related to the ring size of the forming metallacycles, accounts for the site selectivity of C-H activation. Benzylic C(sp3)-H activation possessing less strained five-membered metallacycle compared to the ortho-C(sp2)-H and α-methyl C(sp3)-H activation results in benzylic C(sp3)-H alkylation observed experimentally. Both steric and electronic factors are responsible for the 1,2-insertion regioselectivity for alkyl-substituted alkenes, while electronic factors control the 2,1-insertion manner for vinylsilanes. The analysis of original alkene substrates further strengthens the understanding of the alkene-dependent regioselectivity. These results help us to obtain the mechanistic understanding and are expected to be conducive to the development of new C-H functionalization reactions.


Assuntos
Alcenos , Escândio , Compostos de Anilina , Alquilação , Catálise
6.
J Am Chem Soc ; 145(2): 1407-1422, 2023 Jan 18.
Artigo em Inglês | MEDLINE | ID: mdl-36598430

RESUMO

Grafting metal cations to missing linker defect sites in zirconium-based metal-organic frameworks, such as UiO-66, produces a uniquely well-defined and homotopic catalytically active site. We present here the synthesis and characterization of a group of UiO-66-supported metal catalysts, M-UiO-66 (M = Ni, Co, Cu, and Cr), for the catalytic dimerization of alkenes. The hydrogen-deuterium exchange via deuterium oxide adsorption followed by infrared spectroscopy showed that the last molecular water ligand desorbs from the sites after evacuation at 300 °C leading to M(OH)-UiO-66 structures. Adsorption of 1-butene is studied using calorimetry and density functional theory techniques to characterize the interactions of the alkene with metal cation sites that are found active for alkene oligomerization. For the most active Ni-UiO-66, the removal of molecular water from the active site significantly increases the 1-butene adsorption enthalpy and almost doubles the catalytic activity for 1-butene dimerization in comparison to the presence of water ligands. Other M-UiO-66 (M = Co, Cu, and Cr) exhibit 1-3 orders of magnitude lower catalytic activities compared to Ni-UiO-66. The catalytic activities correlate linearly with the Gibbs free energy of 1-butene adsorption. Density functional theory calculations probing the Cossee-Arlman mechanism for all metals support the differences in activity, providing a molecular level understanding of the metal site as the active center for 1-butene dimerization.


Assuntos
Compostos Organometálicos , Adsorção , Dimerização , Cátions , Zircônio/química , Alcenos , Água/química
7.
J Am Chem Soc ; 145(2): 822-829, 2023 Jan 18.
Artigo em Inglês | MEDLINE | ID: mdl-36603116

RESUMO

Molecular machines offer many opportunities for the development of responsive materials and introduce autonomous motion in molecular systems. While basic molecular switches and motors carry out one type of motion upon being exposed to an external stimulus, the development of molecular systems capable of performing coupled motions is essential for the development of more advanced molecular machinery. Overcrowded alkene-based rotary molecular motors are an ideal basis for the design of such systems as they undergo a controlled rotation initiated by light allowing for excellent spatio-temporal precision. Here, we present an example of a Pd complex of a second-generation rotary motor whose Pd center undergoes a coupled oscillatory motion relative to the motor core upon rotation of the motor. We have studied this phenomenon by UV-vis, NMR, and density functional theory calculations to support our conclusions. With this demonstration of a coupled rotation-oscillation motion powered by a light-driven molecular motor, we provide a solid basis for the development of more advanced molecular machines integrating different types of motion in their operation.


Assuntos
Alcenos , Movimento (Física) , Rotação , Alcenos/química
8.
J Am Chem Soc ; 145(2): 774-780, 2023 Jan 18.
Artigo em Inglês | MEDLINE | ID: mdl-36607827

RESUMO

Intermolecular cyclopropanation of mono-, di-, and trisubstituted olefins with α-bromo-ß-ketoesters and α-bromomalonates under organophotocatalysis is reported. The reaction displays broad functional group tolerance, including substrates bearing acids, alcohols, halides, ethers, ketones, nitriles, esters, amides, carbamates, silanes, stannanes, boronic esters, as well as arenes, and furnishes highly substituted cyclopropanes. The transformation may be performed in the presence of air and moisture with 0.5 mol % of a benzothiazinoquinoxaline as organophotocatalyst. Mechanistic investigations, involving Stern-Volmer quenching, quantum yield determination, and deuteration experiments, are carried out, and a catalytic cycle for the transformation is discussed.


Assuntos
Alcenos , Amidas , Estrutura Molecular , Alcenos/química , Estereoisomerismo , Ciclização , Amidas/química , Catálise
9.
Environ Pollut ; 319: 120971, 2023 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-36603759

RESUMO

Waxy oily sludge (WOS) from petrochemical enterprises has complex components and difficult treatment. Long-term large-scale stacking has seriously threatened human health and the ecological environment. In this paper, a new rapid and effective treatment method combining dispersion and biodegradation in a semi-fluid state was developed for the WOS. The degradation mechanism of the WOS in the bioreactor was preliminarily discussed. The component analysis results showed that the compounds with large molecular weight (M ≥ 282) in the WOS accounted for more than 50%. Among all microbial consortiums, the treatment effect of the consortium FF: NY3 = 9: 1 was the best for treating the crude oil in WOS, which was significantly different from that of a single strain (p < 0.05). Under the optimal nitrogen source NH4NO3 and the concentration of rhamnolipid, the developed high-efficiency microbial consortium (FF: NY3 = 9:1) could remove 85% of the total hydrocarbon pollutants in the 20 L semi-fluid bioreactor within 9 days. The degradation characteristics of WOS components in the bioreactor showed that the developed consortium has good degradation ability for n-alkanes (about 90%), middle- (77.35%)/long-chain (72.66%) isomeric alkanes, alkenes (79.12%), alicyclic hydrocarbons (78.9%) and aromatic hydrocarbons (62.78%). The kinetic analysis results indicated that, in comparison, the middle-chain n-alkanes, middle-chain isomeric saturated alkanes, alkenes, and alicyclic hydrocarbons were most easily removed. The removal rates of long-chain n-alkanes, long-chain isomeric saturated alkanes, and aromatic hydrocarbons were relatively low. The biological toxicity test showed that the germination rate of wheat seeds in treated waxy sludge was Significantly higher than that in untreated waxy sludge (p < 0.01). These results suggest that the new method developed in this paper can treat refractory WOS quickly and effectively. This method lays the foundation for the pilot-scale treatment of the semi-fluid bioreactor.


Assuntos
Petróleo , Esgotos , Humanos , Cinética , Óleos , Hidrocarbonetos/análise , Alcanos/metabolismo , Biodegradação Ambiental , Petróleo/análise , Alcenos
10.
J Chromatogr A ; 1689: 463757, 2023 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-36628807

RESUMO

The olefin/paraffin selectivity offered by ionic liquid (IL) stationary phases can be enhanced through the addition of silver(I) ion, which is well-known to undergo selective complexation with unsaturated compounds. However, such stationary phases often suffer from the loss of chromatographic selectivity as silver(I) ion can be reduced to elemental silver. To maintain the separation performance of silver(I) ion/IL stationary phases, an understanding of factors and conditions that promote the reduction of silver(I) ion is needed. In this study, capillary gas chromatography columns featuring a stationary phase consisting of the 1-decyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([C10MIM+][NTf2-]) IL impregnated with [Ag+][NTf2-] were examined to investigate the effects of temperature, hydrogen content in exposure gas stream, and time of heating/exposure events on olefin selectivity. Retention factors of representative analytes, such as C6 olefins and paraffins as well as aromatic compounds, were measured after subjecting the columns to the aforementioned conditions, followed by an evaluation of selectivity factors over time. Selectivity factors of olefins and aromatic compounds were observed to decrease significantly when the stationary phases were heated to temperatures higher than 110°C as well as being subjected to mixed gas streams containing greater than 50 mol% of hydrogen. As constant column heating temperatures were applied under exposure gas mixtures containing hydrogen and nitrogen, a gradual decrease in analyte selectivity factors was observed under prolonged periods of time. However, application of a ternary gas mixture comprised of 25/50/25 mol% hydrogen/nitrogen/methane resulted in an increase in the 3-hexyne/cis-2-hexene selectivity when measured at 120°C for 60 h, due to a smaller decrease in the retention factor of 3-hexyne compared to cis-2-hexene.


Assuntos
Líquidos Iônicos , Líquidos Iônicos/química , Parafina , Prata/química , Sais , Alcenos , Cromatografia Gasosa/métodos
11.
Chempluschem ; 88(1): e202200432, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36592006

RESUMO

Continuing efforts aimed at performing the 1-decene polymerization to low viscosity polyalphaolefins (PAO)s using a less hazardous AlCl3 catalyst than boron-based analogs, the basic mechanisms of this system were revealed in this research. In this aspect, neat AlCl3 and AlCl3 /toluene were carried out to perform 1-decene polymerizations. Microstructure analyses of the as-synthesized oils revealed low molecular weight (708 vs. 1529 g/mol), kinematic viscosity (KV100 =6.4 vs. 22.2 cSt), and long chain branching (82.1 vs. 84.7) of PAO from the system containing toluene solvent. Furthermore, NMR analysis confirmed various types of short chain branch (SCB) with the inclusion of toluene ring in the structure of final PAO chains. Then, to shed light on the basic mechanisms of cationic polymerization of 1-decene including: i) chain initiation, ii) chain transfer to the monomer, iii) isomerization of the carbocation via a chain walking mechanism (causes different SCB length), and iv) binding of toluene ring to the propagating PAO chain (to yield aromatic containing oligomers), molecular modeling at the DFT level was employed. The energies obtained confirmed the ease of carbocation isomerization and chain transfer mechanisms in toluene medium, which well confirms the highly branched structure experimentally obtained for related PAO.


Assuntos
Alcenos , Tolueno , Alcenos/química , Polimerização , Tolueno/química , Modelos Moleculares , Catálise
12.
Org Biomol Chem ; 21(2): 300-305, 2023 01 04.
Artigo em Inglês | MEDLINE | ID: mdl-36514892

RESUMO

Here, we developed an air-stable, earth-abundant cobalt(III)-catalyzed regioselective mono-olefination of arenes directed by urea under mild conditions through a cross-dehydrogenative coupling (CDC) process. Under the optimized conditions, a high regioselectivity of mono-olefination was achieved with various electron-rich and electron-deficient arenes, which afforded E-alkenylated products (with yields of up to 90%). In contrast to the conditions used for noble-metal-catalyzed olefination directed by weakly coordinating groups, our reaction was operated under mild conditions, including mild temperature (40 °C) and non-metallic oxidant.


Assuntos
Alcenos , Cobalto , Catálise , Estrutura Molecular , Oxidantes
13.
Org Lett ; 25(1): 93-98, 2023 01 13.
Artigo em Inglês | MEDLINE | ID: mdl-36546834

RESUMO

The construction of molecular skeletons and modification of molecules using widely available and easily prepared alcohols as radical precursors for coupling reactions are significant and challenging subjects. We herein report a straightforward strategy for the dehydrogenative ring-opening alkenylation of cycloalkanols with alkenes by combining a proton-coupled electron transfer strategy and a dual photoredox and cobalt catalysis system. With this approach, a series of distally unsaturated ketones were obtained in 17-83% yields with high E selectivity.


Assuntos
Álcoois , Prótons , Humanos , Transporte de Elétrons , Catálise , Alcenos , Cobalto
14.
Org Lett ; 25(1): 42-46, 2023 01 13.
Artigo em Inglês | MEDLINE | ID: mdl-36576234

RESUMO

A novel class of stable monoareno-pentalenes is introduced that have an olefinic proton on each five-membered ring of the pentalene subunit. Their synthesis was accomplished via a regioselective carbopalladation cascade reaction between ortho-arylacetyleno gem-dibromoolefins and TIPS-acetylene. These molecules could be experimental probes of magnetic (anti)aromaticity effects.


Assuntos
Alcenos , Prótons , Estrutura Molecular , Acetileno
15.
Org Lett ; 25(1): 236-239, 2023 01 13.
Artigo em Inglês | MEDLINE | ID: mdl-36583698

RESUMO

The mechanistic pathway for the formation of 1,2-oxazetes by reaction of olefins with nitrous anhydride has been clarified. The initial reaction intermediate, a ß-nitroso nitrite ester that is sensitive to light, undergoes O-NO fission to form a ß-nitroso alkoxy radical, even with ambient fluorescent lighting but much faster with blue light irradiation. The oxygen of the alkoxy radical subsequently adds to the adjacent nitroso group to generate a cyclic four-membered nitrosyl radical. The 1,2-oxazete is then produced by elimination to generate the C═N bond. No 1,2-oxazete formation occurs in the dark.


Assuntos
Alcenos , Óxido Nítrico , Nitritos
16.
J Environ Sci (China) ; 123: 417-429, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36522003

RESUMO

Based on one-year observation, the concentration, sources, and potential source areas of volatile organic compounds (VOCs) were comprehensively analyzed to investigate the pollution characteristics of ambient VOCs in Haikou, China. The results showed that the annual average concentration of total VOCs (TVOCs) was 11.4 ppbV, and the composition was dominated by alkanes (8.2 ppbV, 71.4%) and alkenes (1.3 ppbV, 20.5%). The diurnal variation in the concentration of dominant VOC species showed a distinct bimodal distribution with peaks in the morning and evening. The greatest contribution to ozone formation potential (OFP) was made by alkenes (51.6%), followed by alkanes (27.2%). The concentrations of VOCs and nitrogen dioxide (NO2) in spring and summer were low, and it was difficult to generate high ozone (O3) concentrations through photochemical reactions. The significant increase in O3 concentrations in autumn and winter was mainly related to the transmission of pollutants from the northeast. Traffic sources (40.1%), industrial sources (19.4%), combustion sources (18.6%), solvent usage sources (15.5%) and plant sources (6.4%) were identified as major sources of VOCs through the positive matrix factorization (PMF) model. The southeastern coastal areas of China were identified as major potential source areas of VOCs through the potential source contribution function (PSCF) and concentration-weighted trajectory (CWT) models. Overall, the concentration of ambient VOCs in Haikou was strongly influenced by traffic sources and long-distance transport, and the control of VOCs emitted from vehicles should be strengthened to reduce the active species of ambient VOCs in Haikou, thereby reducing the generation of O3.


Assuntos
Poluentes Atmosféricos , Ozônio , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/análise , Emissões de Veículos/análise , Poluentes Atmosféricos/análise , Monitoramento Ambiental/métodos , Ozônio/química , Alcanos/análise , Alcenos , China
17.
Org Lett ; 25(1): 195-199, 2023 01 13.
Artigo em Inglês | MEDLINE | ID: mdl-36583971

RESUMO

Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes to more challenging α,ß-unsaturated carbonyl derivatives to the corresponding benzylic fluorides. This method can also be applied to the late-stage modification of pharmaceutical derivatives. Mechanistic studies suggest that the generation of a high-valent palladium intermediate via anodic oxidation is the crucial step in this electrocatalytic hydrofluorination.


Assuntos
Alcenos , Paládio , Flúor , Estrutura Molecular , Catálise
18.
Chem Commun (Camb) ; 59(4): 462-465, 2023 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-36519429

RESUMO

The water-mediated tosylation of alkenes with tosyl cyanide was discovered. Experimental investigations revealed that the reaction was initiated by the in situ formation of sulfinyl sulfone in the presence of water. The sulfinyl sulfone species decomposed to a sulfonyl radical and a sulfinyl radical through homolytic fission. The vinyl sulfone was afforded via sequential addition of the alkene to the sulfonyl radical and the sulfinyl radical, followed by ß-elimination of a sulfinyl moiety.


Assuntos
Alcenos , Água , Cianetos , Sulfonas
19.
Chem Commun (Camb) ; 59(4): 446-449, 2023 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-36519364

RESUMO

Herein, we disclose the first report on the generation of cyanonitrone in situ from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Surprisingly, the reductive ring-opening of cyanoisoxazolidines was followed by a spontaneous lactonization to produce fused tricyclic amino lactones. Moreover, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines could be cleaved to obtain 1,3-amino alcohols.


Assuntos
Alcenos , Amino Álcoois , Ciclização , Alcenos/química , Lactonas/química , Reação de Cicloadição
20.
Chem Commun (Camb) ; 59(4): 482-485, 2023 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-36530042

RESUMO

The Ni-catalyzed reactions of benzamides with bicyclic alkenes were explored using DFT calculations. An unprecedented "N-H deprotonation circumvented" catalytic mechanism was proposed, over the more common N-H/C-H activation mechanism, in which (i) the circumvention of N-H deprotonation ensures the presence of N-H⋯O hydrogen bond interaction, thereby stabilizing the critical ortho-C-H functionalization TS; and (ii) the N-H moiety retention results in a weak N⋯Ni σ-coordination, which is flexible to the configurational conversion during the key alkene insertion. These overlooked aspects of the functionalized N,N-bidentate directing groups will aid the design of new related catalytic reactions.


Assuntos
Antipsicóticos , Benzamidas , Benzamidas/química , Alcenos/química , Catálise , Teoria da Densidade Funcional
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