ChemSusChem
·
2015
·Vol. 8
·期 12
·2066-2072
·
IF 7.657
Yehong Wang,Jian Zhang,Jing Liu,Chaofeng Zhang,Zhixin Zhang,Jie Xu,Shutao Xu,Fangjun Wang,Feng Wang
Graphical CO 2 -mediated reactions: CO 2 -mediated metathesis reactions between amines and DMF to synthesize formamides are described. The N -formylation of amines to formamides is achieved by activating amines, not DMF, via a C N and N H bond metathesis reaction. Using this method, primary, secondary, aromatic, and heterocyclic amines as well as diamines can be obtained with good to excellent formamide yields. Herein, we report CO 2 -mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good-to-excellent conversions and selectivities under mild conditions. This strategy employs CO 2 as a mediator to activate the amine under metal-free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the N -carbamic acid as an intermediate through the weak acid–base interaction between CO 2 and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.
研究领域:
有机化学
·
绿色化学
✓ 已验证
DOI
PubMed
高影响因子
ENVIRONMENTAL RESEARCH
·
2023
·
IF 8.3
Baihui Chi,Fei Li,Xukang Wang,Haixia Pan,Xianliang Yi,Yang Liu,Jingjing Zhan,Xuwang Zhang,Hao Zhou,Wenyuan Wang
N,N-dimethylformamide (DMF) is widely used in various industries, but its direct release into water poses high risks to human beings. Although a lot of DMF-degrading bacteria has been isolated, limited studies focus on the degradation preference among DMF and its analogues. In this study, an efficient DMF mineralization bacterium designated Aminobacter ciceronei DMFA1 was isolated from marine sediment . When exposed to a 0.2% DMF (∼1900 mg/L), strain DMFA1 exhibited a degradation efficiency of 100% within 4 days. The observed growth using formamide as the sole carbon source implied the possible DMF degradation pathway of strain DMFA1. Meanwhile,the strain DMFA1 possesses a broad-spectrum substrate degradation, which could effectively degraded 0.2% N,N-dimethylacetamide (DMAC) and N-methylformamide (NMF). Genomic analysis further confirmed the supposed pathway through annotating the genes encoding N, N-dimethylformamidase (DMFase), formamidase, and formate dehydrogenase . The existence of sole DMFase indicating its substrate specificity controlled the preference of DMAc of strain DMFA1. By integrating multiple sequence alignment, homology modeling and molecular docking, the preference of the DMFase in strain DMFA1 towards DMAc are related to: 1) Mutations in key active site residues; 2) the absence of small subunit; and 3) no energy barrier for substrates entering the active site.
研究领域:
环境微生物学
·
生物降解
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF HETEROCYCLIC CHEMISTRY
·
2021
·Vol. 58
·期 11
·2189-2202
·
IF 2.193
Abdalla Khallaf,Ping Wang,Shuping Zhuo,Hongjun Zhu,Hui Liu
The preparation of novel anthranilic diamide derivatives is extremely important for agricultural pest control. In this study, pyridylpyrazole-4-carboxamides containing a 1,3,4-oxadiazole ring were designed and synthesized via the dehydration of aromatic hydrazine derivatives and formanilides in the presence of an alkali. The insecticidal activities of these new compounds against the diamondback moth ( Plutella xylostella ) were evaluated. N-(4-chloro-2-methyl-6-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-5-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carboxamide ( 8h6 ) showed 67%, 50%, 34%, 20%, and 17% activity at concentrations of 100, 50, 10, 5, and 1 μg ml −1 , respectively. Density functional theory calculations showed that the introduction of the 1,3,4-oxadiazole ring significantly changed the electron distributions in both the highest occupied and lowest unoccupied molecular orbitals, resulting in these compounds having much larger energy gaps than the well-known insecticide chlorantraniliprole, which may account for their lower activity. The results of this study demonstrate that anthranilic diamides substituted with a 1,3,4-oxadiazole ring are effective insecticides that can be used for pest management.
研究领域:
农业科学
·
有机化学
✓ 已验证
DOI
高影响因子
BIOTECHNOLOGY LETTERS
·
2021
·Vol. 43
·期 8
·1617-1624
·
IF 2.461
Wang Liuzhu,Jiang Shuiqin,Sun Yangyang,Yang Zeyu,Chen Zhi,Wang Hualei,Wei Dongzhi
Objectives Catalytic promiscuity, or the ability to catalyze a secondary reaction, provides new opportunities for industrial biocatalysis by expanding the range of biocatalytic reactions. Some nitrilases converting nitriles to amides, referred to as the secondary activity, show great potential for amides production. And our goal was exploiting the amide-forming potential of nitrilases. Results In this study, we characterized and altered the secondary activity of nitrilase from Acidovorax facilis 72 W (Nit72W) towards different substrates. We increased the secondary activity of Nit72W towards 2-cyanopyridine by 196-fold and created activity toward benzonitrile and p-nitrophenylacetonitrile by modifying the active pocket. Surprisingly, the best mutant, W188M, completely converted 250 mM 2-cyanopyridine to more than 98% 2-picolinamide in 12 h with a specific activity of 90 U/mg and showed potential for industrial applications. Conclusions Nit72W was modified to increase its secondary activity for the amides production, especially 2-picolinamide.
研究领域:
生物化学
·
工业生物技术
✓ 已验证
DOI
PubMed
高影响因子
ChemCatChem
·
2021
·Vol. 13
·期 19
·4159-4163
·
IF 5.686
Dongxia Jiao,Yehong Wang,Zhixin Zhang,Jian Zhang,Lijun Lei,Feng Wang
Graphical Synthetic methods : We designed a hydroxyapatite (HAP)-stabilized, positively charged Ru-based catalyst which can efficiently catalyze the formylation reaction of amines with CO for the synthesis of formamide. The combination of characterization results and control experiments showed that positively charged Ru species, particularly the hydrated RuO x particles on the surface were essential to the high catalytic activity of Ru-HAP in the formylation reaction. Formamide is an important solvent and synthetic intermediate. Herein, we designed a hydroxyapatite (HAP)-stabilized, positively charged Ru-based catalysts which can efficiently catalyze the formylation reaction of amines with CO for the synthesis of formamide. The Ru-HAP showed excellent catalytic performance in N,N-Dimethylformamide (DMF) synthesis, with about 75 % dimethylamine conversion and >99 % DMF selectivity at 300 h of continuous reaction. The combination of characterization results and control experiments showed that positively charged Ru species, including hydrated RuO x and Ru 3+ species, were catalytically active. In particular, the surface RuO x species were more active than the Ru 3+ species located within the HAP framework.
研究领域:
催化
·
材料科学
·
化学工程
·
无机化学
✓ 已验证
DOI
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2019
·
IF 2.298
Xingchang Cha,Jun Gao,Yi Zhang,Ziqi Cui,Dongmei Xu,Lianzheng Zhang,Yinglong Wang
For the purpose of separating nitrogen compounds, pyrrole and indole, N-methylformamide (NMF) was selected as the extractive solvent. The liquid–liquid equilibrium (LLE) data for {NMF + pyrrole/indole + alkanes} systems were measured at 298.15 K under atmospheric pressure of 101.3 kPa. The triangular diagrams of the above eight systems, {NMF + pyrrole/indole + n-hexane/n-heptane/n-decane/n-dodecane}, were classified as Treybal’s type I. Meanwhile, the nonrandom two-liquid (NRTL) and universal quasi-chemical (UNIQUAC) activity coefficient models were applied to correlate the LLE data, and the UNIQUAC model shows better agreement than the NRTL model. In addition, the distribution constant and selectivity factor were calculated on the basis of the experimental data and utilized to investigate the extraction capabilities of NMF for pyrrole and indole.
研究领域:
化学工程
·
物理化学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF ASIA-PACIFIC ENTOMOLOGY
·
2024
·
IF 1.1
Qing-Hua Xiao,Wu-Ye Li,Jin Zhang,Jia-Min Yu,Dong-Yang Liu,Jiang-Nan Peng,Mao-Ye Li,Su Liu
In insects, the transcription factor cap ‘n’ collar isoform C (CncC) plays a critical role in the regulation of multiple genes involved in insecticide detoxification. Knockdown of CncC genes leads to increased susceptibility to different types of insecticides in several insect species. However, the CncC gene has not yet been fully characterized in the black cutworm Agrotis ipsilon , a notorious insect pest that causes severe damage to field crops. In this study, the CncC gene (designated AiCncC ) was identified from A. ipsilon . Exposure to a median lethal concentration (LC 50 ) of chlorantraniliprole (CAP) or phoxim (PHO) strongly increased the expression of AiCncC . Silencing of AiCncC by RNA interference significantly increased the susceptibility of A. ipsilon larvae to both insecticides. Moreover, CncC/Maf binding sites were predicted in the putative promoters of two glutathione S -transferase (GST) genes ( AiGSTe1 and AiGSTu1 ) involved in the detoxification of CAP and PHO. The transcription levels of AiGSTe1 and AiGSTu1 were dramatically decreased by silencing AiCncC . These findings indicate that AiCncC is associated with CAP and PHO susceptibility through the regulation of GST genes.
研究领域:
昆虫学
·
分子生物学
·
害虫防治
✓ 已验证
产品关联
DOI
高影响因子
Vietnam Journal of Chemistry
·
2023
·Vol. 61
·期 2
·204-209
·
IF 0.9
Nguyen Van Vinh Ha,Nguyen Thi Thu Ha,Ong Ngoc Khanh,Dinh Truc Phuong,Ho Thanh Nhat,Nguyen Thanh Tung
Herein we reported a method for copper pivalate mediated, directed functionalization of ortho C−H bonds in (2-methylthio)aniline benzamides. Diaryl disulfides were used for thiolation, while successful phenoxylation was obtained with phenol as the coupling agent. Our report marks a rare example for flexible transformation of benzamide C(sp 2 )−H bonds into the corresponding unsymmetrical diaryl ethers and thioethers.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
高影响因子
INTERNATIONAL JOURNAL OF PHARMACEUTICS
·
2021
·
IF 5.875
Hongji Liu,Jinju Nie,H.C. Stephen Chan,Hailu Zhang,Liang Li,Hongqing Lin,Henry H.Y. Tong,Ande Ma,Zhengzheng Zhou
Herein, we reported a new bergenin : 4-aminobenzamide ( BGN-4AM ) cocrystal with significantly enhanced solubility and low hygroscopicity probed from two aspects such as phase solubility diagrams and theoretical calculations. Compared with anhydrous BGN , BGN-4AM solubilities in water and different buffer solutions (pH = 1.2, 4.5, 6.8) increase significantly. It is noted that BGN-4AM solubility in pH = 6.8 buffer solution presents 32.7 times higher than anhydrous BGN . Interestingly, BGN-4AM (0.31 ± 0.07%) showcases lower hygroscopicity than anhydrous BGN (9.31 ± 0.16%). The predicted and experimental solubilities agree with each other when considering solubility product ( K sp ) and solution binding constant ( K 11 ) in phase solubility diagrams, indicating the solution complexes formation occurs. Further crystal surface-water interactions and Bravais, Friedel, Donnay-Harker (BFDH) analyses based on Density Functional Theory with dispersion correction (DFT- d ) methods support the enhanced solubility. The water probe demonstrates an average interaction energy of −6.48 kcal/mol on the 002 plane of BGN-4AM , and only −5.47 kcal/mol on the 011 plane of BGN monohydrate. The lower lattice energy of BGN-4AM guarantees its lower hygroscopicity than BGN monohydrate. BGN-4AM with enhanced solubility and low hygroscopicity can be a potential candidate for further formulation development.
研究领域:
药剂学
·
理论化学
✓ 已验证
DOI
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2021
·
IF 2.694
Xiaoyu Wang,Jiale Wang,Lijun Ji,Bin Wu,Kui Chen,Yanyang Wu
Wastewater containing DMF (N,N-dimethylformamide) and salt is generated in production of many chemicals and medicines. The composition of phase equilibrium should be known primarily for the recovery of DMF from salt-containing wastewater by solvent extraction. In this study, liquid–liquid equilibrium (LLE) and solubility data of water + DMF + chloroform in the presence of NaCl with various concentrations of 0, 2.5, 5.0, 7.5, 10.0, and 13.3 wt % and Na2SO4 with concentrations of 1.5 and 2.5 wt % were determined at T = 298.2 K and atmospheric pressure. Besides, the salt effect on the LLE data was investigated. Compared with the salt-free system, the salt led to an enhancement in the maximum DMF distribution coefficient by 13.4–102.6% for 2.5–13.3 wt % NaCl and 16.2–31.7% for 1.5–2.5 wt % Na2SO4, respectively. Since the distribution coefficient of water increased concurrently, the separation factor barely changed and the two-phase region expanded outward slightly. At the same salt mass fraction, the order of salting-out effect strength on extraction was Na2SO4 > NaCl, which was in good agreement with the Hofmeister series. The reliability of the experimental values was verified through the Eisen–Joffe equation. The NRTL thermodynamic model was applied to correlate the experimental data with a root-mean-square deviation less than 0.0062. The coherent consistency of the model parameters for the salt-free system was checked by topological analysis based on the Gibbs tangent plane test.
研究领域:
化学工程
·
环境科学
✓ 已验证
DOI
高影响因子
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
·
2016
·Vol. 15
·期 11
·1442-1447
·
IF 2.235
Xu Ruixin,He Minghui,Yang Jianwen
Benzoylformamides (BFAs) are proposed as photocaged bases for redox free radical photopolymerization (FRP). Initially the dissolving capacity of BFAs was evaluated. Besides our previously reported photo-latent anion polymerization, BFAs, as versatile photocaged bases, can not only initiate the FRP of acrylates unassisted, but also perform redox FRP in combination with a benzoyl peroxide initiator. We detail a model photopolymerization in the presence of BFA-dBA ( N , N -dibenzyl-2-oxo-2-phenylacetamide) as the photocaged base. In combination with a benzoyl peroxide initiator, BFAs are able to initiate the amine-mediated redox photopolymerization of acrylates, and enhance the photopolymerization rate. Finally, we investigated the mechanism of the radical formation to initiate the redox FRP, as exemplified by BFA-dBA.
研究领域:
材料科学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CARBON
·
2015
·
IF 6.196
Jianping Chen,Weili Shi,Dong Fang,Tao Wang,Jing Huang,Qi Li,Ming Jiang,Lei Liu,Qiong Li,Lijie Dong,Qing Wang,Chuanxi Xiong
Up to now, the cost-effective mass production of pristine graphene sheets remains a significant challenge. We report a binary solvent system of dimethylformamide and n -butylalcohol that facilitates the high concentration production of unoxidized graphene through liquid-exfoliation assisted with sonication . A stable dispersion with concentration as high as 6.5 mg/ml, was received via this method. The conductivity of a film made from the graphene sheets had a conductivity of 27,000 S/m. The supercapacitor fabricated by graphene exhibits a giant capacitance of 600 F/g and an outstanding long-term stability.
研究领域:
材料科学
·
能源科学
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）