Journal of Physical Organic Chemistry最新文献

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Theoretical descriptions on novel heteroatoms analogs of Hammick silylenes using DFT 新型汉密克硅烯杂原子类似物的DFT理论描述
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-06-01 DOI: 10.1002/poc.4547
M. Moradian
{"title":"Theoretical descriptions on novel heteroatoms analogs of Hammick silylenes using DFT","authors":"M. Moradian","doi":"10.1002/poc.4547","DOIUrl":"https://doi.org/10.1002/poc.4547","url":null,"abstract":"","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49156848","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Theoretical descriptions on novel heteroatoms analogs of Hammick silylenes using density functional theory 利用密度泛函理论对新型Hammick甲硅烷杂原子类似物的理论描述
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-06-01 DOI: 10.1002/poc.4547
Majid Moradian
{"title":"Theoretical descriptions on novel heteroatoms analogs of Hammick silylenes using density functional theory","authors":"Majid Moradian","doi":"10.1002/poc.4547","DOIUrl":"https://doi.org/10.1002/poc.4547","url":null,"abstract":"<p>In this investigation, we have been compared and contrasted the substituent effects on stability using Δ<i>Ε</i><sub>s-t</sub> (<i>E</i><sub>t</sub> <i>− E</i><sub>s</sub>), frequency, Δ<i>Ε</i><sub>HOMO-LUMO</sub> (<i>E</i><sub>LUMO</sub> <i>− E</i><sub>HOMO</sub>), polarity, polarizability, Mülliken charge distribution and reactivity descriptors of the singlet and triplet Hammick silylenes derived from silapyridine-4-ylidene (<b>1-s</b>, <b>2x-s</b>, <b>3x-s</b> and <b>1-t</b>, <b>2x-t</b>, <b>3x-t</b>; x = NH, PH, AsH, O, S, and Se) as well as the synthesized dialkylsilylenes by West (<b>4-s</b>), Denk (<b>5-s</b>), and Kira (<b>6-s</b>). In all cases, singlet (s) silylenes appear as ground states, exhibiting more stability than their corresponding triplet (t) states. All the above s and t silylenes appear as minima on their energy surfaces showing the positive force constant and the positive harmonic vibration frequency. Regardless of how orchestrated substituent groups in either “W” or “chair” position; the most stability is demonstrated by substitution of NH, and O groups in the fused pyrrole ring, while the least stability is considered by Kira's silylene. In contrast to previous report on the <i>N</i>-Heterocyclic Hammick carbenes, silylenes, and germylenes (NHCs, NHSis, and NHGes) that size, type, orientation, and the number of fused rings pronounced effect on stability of the corresponding divalent species, here σ-donor/π-donor groups (such as PH, AsH, S, and Se) similar to σ-acceptor/π-donor groups (such as NH and O) stabilize their corresponding silylenes. Furthermore, the scrutinized singlet silylenes reveal lesser nucleophilicity (<i>N</i>), greater electrophilicity (<i>ω</i>), higher chemical potential (<i>μ</i>), higher global hardness (<i>η</i>), and lower global softness (<i>S</i>) than the analogous triplet silylenes. All singlet and triplet species show the maximum electronic charge (Δ<i>N</i><sub>max</sub>) with positive sign.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50115855","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of 3-arylated chlorophyll-a derivatives via Diels–Alder reaction and their atropisomerism Diels - Alder反应合成3 -芳基化叶绿素- a衍生物及其消旋异构
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-18 DOI: 10.1002/poc.4546
Saki Kichishima, Hiroaki Maeda, Hitoshi Tamiaki
{"title":"Synthesis of 3-arylated chlorophyll-a derivatives via Diels–Alder reaction and their atropisomerism","authors":"Saki Kichishima,&nbsp;Hiroaki Maeda,&nbsp;Hitoshi Tamiaki","doi":"10.1002/poc.4546","DOIUrl":"10.1002/poc.4546","url":null,"abstract":"<p>Methyl pyropheophorbides-<i>a</i> possessing an <i>o</i>/<i>m</i>-(methoxycarbonyl)phenyl group at the 3-position were prepared by Diels–Alder reaction of 3-(<i>trans</i>-1,3-butadienyl)chlorin with methyl propiolate and successive didehydrogenation of the resulting 1,4-cyclohexadienes. The 3-arylated chlorin bearing the sterically demanding <i>o</i>-COOMe group as the major product was a 1:1 mixture of high-performance liquid chromatography-separable rotational isomers around the C3–C3<sup>1</sup> bond, while the minor product with the <i>m</i>-COOMe was less sterically hindered to exhibit rapid atropisomerization at room temperature. The 3-aryl group of the major product was nearly perpendicular to the chlorin π-system and less conjugated with the chlorin moiety than that of the minor product wherein more π-conjugation occurred to give slightly red-shifted Qy bands. Although both the atropisomers of the <i>o</i>-substitute in dichloromethane showed similar visible absorption bands and fluorescence emission data, their circular dichroism bands in the ultraviolet-C light region were dependent on the stereochemistry.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43924945","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
On the hydroperoxyl radical scavenging activity of estrogens in lipid and aqueous media: A theoretical study 脂质和水介质中雌激素清除羟基自由基活性的理论研究
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-18 DOI: 10.1002/poc.4545
María F. Hernández-Hernández, Eduardo A. Tejeda-Medina, César Espinoza, Manuel E. Medina
{"title":"On the hydroperoxyl radical scavenging activity of estrogens in lipid and aqueous media: A theoretical study","authors":"María F. Hernández-Hernández,&nbsp;Eduardo A. Tejeda-Medina,&nbsp;César Espinoza,&nbsp;Manuel E. Medina","doi":"10.1002/poc.4545","DOIUrl":"10.1002/poc.4545","url":null,"abstract":"<p>Despite the evidence on the antioxidant capability of estrogens, little is known about their reaction mechanism involved. According to the above, this work was carried out on the hydroperoxyl radical scavenging activity of three estrogens—estriol (EST), estradiol (ESD), and estrone (ESO)—in lipid and aqueous media by theoretical methodologies employing the DFT. In lipid and aqueous media, hydrogen transfer was the main reaction mechanism on the hydroperoxyl radical scavenging of EST, ESD, and ESO. The reaction rate constants calculated in lipid media were 1.08 × 10<sup>6</sup>, 8.39 × 10<sup>4</sup>, and 6.43 × 10<sup>4</sup> M<sup>−1</sup> s<sup>−1</sup> for the EST, ESD, and ESO, respectively. The reaction rate constants calculated in aqueous media were 3.00 × 10<sup>6</sup>, 3.58 × 10<sup>6,</sup> and 1.05 × 10<sup>8</sup> M<sup>−1</sup> s<sup>−1</sup> on the hydroperoxyl radical scavenging activity of EST, ESD, and ESO, respectively. The results also showed that the EST, ESD, and ESO estrogens could scavenge high reactivity radicals through the SET mechanism in aqueous media. In lipid media, estrogens are moderate antioxidants, whereas in aqueous media, these are good antioxidants. These theoretical results support the intrinsic antioxidant activity of EST, ESD, and ESO estrogens in lipid and aqueous media.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48227781","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
2,3,5,6-Tetrafluoro-1,4-phenylenedinitrene: A dinitrene with near degenerate singlet and triplet states 2,3,5,6‐四氟‐1,4‐苯二腈:具有近简并单重态和三重态的二腈
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-15 DOI: 10.1002/poc.4544
Adrian Portela-Gonzalez, Enrique Mendez-Vega, Wolfram Sander
{"title":"2,3,5,6-Tetrafluoro-1,4-phenylenedinitrene: A dinitrene with near degenerate singlet and triplet states","authors":"Adrian Portela-Gonzalez,&nbsp;Enrique Mendez-Vega,&nbsp;Wolfram Sander","doi":"10.1002/poc.4544","DOIUrl":"10.1002/poc.4544","url":null,"abstract":"<p>The dinitrene 2,3,5,6-tetrafluoro-1,4-phenylenedinitrene was synthesized by photolysis of matrix-isolated 1,4-diazido-2,3,5,6-tetrafluorobenzene at 365 or 405 nm in high yields at cryogenic temperatures and characterized by FT-IR, UV-Vis, and EPR spectroscopy. The electronic structure of the dinitrene is described best as a quinoidal diradical with an open-shell singlet ground state and a triplet state laying only 650 ± 5 cal/mol higher in energy. Irradiation with λ = 254 nm results in fragmentation of the dinitrene into FCCF and several olefins which on prolonged photolysis fragment into FCCCN, FCCNC, and FCN.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/poc.4544","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46538326","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An unexpected isomerisation of Isoquinuclidines 异奎宁环类化合物的意外异构化
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-10 DOI: 10.1002/poc.4518
Rebeca G. Moura, Patrick R. Batista, Lucas C. Ducati, Lydia F. Yamaguchi, Liliana Marzorati
{"title":"An unexpected isomerisation of Isoquinuclidines","authors":"Rebeca G. Moura,&nbsp;Patrick R. Batista,&nbsp;Lucas C. Ducati,&nbsp;Lydia F. Yamaguchi,&nbsp;Liliana Marzorati","doi":"10.1002/poc.4518","DOIUrl":"https://doi.org/10.1002/poc.4518","url":null,"abstract":"<p>The Diels–Alder reaction of three chiral dihydro-2H-[2,3-a]oxazolopyridines with <i>N</i>-methylmaleimide afforded the corresponding chiral cycloadducts as diastereomeric mixtures. In the presence of a solvent, some of the originally formed adducts underwent isomerisation to new isoquinuclidines.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50127958","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A computational study of double perovskites A2BI6 (A = Cs, K, Rb; B = Pt, Sn) invoking density functional theory 双钙钛矿a2bi6 (A = Cs, K, Rb)的计算研究B = Pt, Sn)调用密度泛函理论
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-07 DOI: 10.1002/poc.4519
Bobby Solanki, Pooja Sharma, Prabhat Ranjan, Pancham Kumar, Tanmoy Chakraborty
{"title":"A computational study of double perovskites A2BI6 (A = Cs, K, Rb; B = Pt, Sn) invoking density functional theory","authors":"Bobby Solanki,&nbsp;Pooja Sharma,&nbsp;Prabhat Ranjan,&nbsp;Pancham Kumar,&nbsp;Tanmoy Chakraborty","doi":"10.1002/poc.4519","DOIUrl":"10.1002/poc.4519","url":null,"abstract":"<p>Lead-free double perovskite materials A<sub>2</sub>BI<sub>6</sub> (A = Cs, K, Rb; B = Pt and Sn) have been studied and analyzed invoking density functional theory (DFT). Computed values of the HOMO–LUMO gap for lead-free double perovskites material A<sub>2</sub>BI<sub>6</sub> are found in the range of 1.062–2.811 eV. The energy gaps of K<sub>2</sub>PtI<sub>6</sub>, K<sub>2</sub>SnI<sub>6</sub>, and Rb<sub>2</sub>SnI<sub>6</sub> are in the optimal energy gap range (0.9 to 1.6 eV) required for a lead-free double perovskite system. Conceptual DFT-based descriptors, viz., molecular hardness, softness, electronegativity, electrophilicity index, dipole moment, and polarizability, are computed. The result reveals that K<sub>2</sub>PtI<sub>6</sub> shows high efficacy towards electron injection and may show the maximum electron driving force. The optical properties—refractive index and dielectric constant—of these perovskites are also computed. The maximum value of refractive index and dielectric constant is found for K<sub>2</sub>PtI<sub>6</sub>. Our computed results are in good agreement with the available experimental and other theoretical data. Perovskite materials K<sub>2</sub>PtI<sub>6</sub>, K<sub>2</sub>SnI<sub>6</sub>, and Rb<sub>2</sub>SnI<sub>6</sub> display a suitable energy gap as well as a high refractive index and dielectric constant, which makes them suitable for photovoltaic applications.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43533054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
The conformational behavior and structure of monosubstituted 1,3,5-trisilacyclohexanes—Part III: 1-Methyl-1,3,5-trisilacyclohexane 单取代1,3,5-三硅环己烷的构象行为和结构——第三部分:1-甲基-1,3,5-三硅环己烷
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-04 DOI: 10.1002/poc.4514
Liubov E. Kuzmina, Sergey A. Shlykov, Ingvar Arnason, Nanna R. Jonsdottir
{"title":"The conformational behavior and structure of monosubstituted 1,3,5-trisilacyclohexanes—Part III: 1-Methyl-1,3,5-trisilacyclohexane","authors":"Liubov E. Kuzmina,&nbsp;Sergey A. Shlykov,&nbsp;Ingvar Arnason,&nbsp;Nanna R. Jonsdottir","doi":"10.1002/poc.4514","DOIUrl":"https://doi.org/10.1002/poc.4514","url":null,"abstract":"<p>1-Methyl-1,3,5-trisilacyclohexane was synthesized and its structure and conformational properties have been determined by gas-phase electron diffraction (GED) and quantum chemical (QC) calculations. The molecule may exist in two forms differing from each other by the substituent's position. QC results show that the equatorial conformer is predicted to be slightly more stable than the axial conformer; note that one method (M06-2X) with basis set 6-311G** shows an equal amount of Ax and Eq conformers: ratio (Ax/Eq) = (30–50):(70–50)% (depending on the method and basis set). From the GED data, the molar fractions of the conformers were found to be Ax:Eq = 54(10):46(10) at 280(5) K. A temperature-dependent Raman experiment resulted in an Ax:Eq ratio of 58(4):42(4). Conformational properties are compared in series of analogous 1-X-1-(hetero)cyclohexanes.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"50120732","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Effects of solvents on excited‐state proton transfer behaviors and photophysical property of 3NTF 溶剂对3NTF激发态质子转移行为和光物理性质的影响
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-01 DOI: 10.1002/poc.4516
Guikun Lin, Wen‐Lin Xie, Yao Xiao, Shiyi Peng, Yao‐Dong Song, Qian‐Ting Wang
{"title":"Effects of solvents on excited‐state proton transfer behaviors and photophysical property of 3NTF","authors":"Guikun Lin, Wen‐Lin Xie, Yao Xiao, Shiyi Peng, Yao‐Dong Song, Qian‐Ting Wang","doi":"10.1002/poc.4516","DOIUrl":"https://doi.org/10.1002/poc.4516","url":null,"abstract":"","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46702663","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Reactivity of bis(2-chloroprop-2-enyl)sulfide in the system hydrazine hydrate/alkali: A quantum chemical insight 双(2-氯丙-2-烯基)硫化物在水合肼/碱体系中的反应性:量子化学研究
IF 1.8 4区 化学
Journal of Physical Organic Chemistry Pub Date : 2023-05-01 DOI: 10.1002/poc.4515
Nikita V. Teplyashin, Alexander S. Bobkov, Nikolai A. Korchevin, Igor B. Rozentsveig, Nadezhda M. Vitkovskaya
{"title":"Reactivity of bis(2-chloroprop-2-enyl)sulfide in the system hydrazine hydrate/alkali: A quantum chemical insight","authors":"Nikita V. Teplyashin,&nbsp;Alexander S. Bobkov,&nbsp;Nikolai A. Korchevin,&nbsp;Igor B. Rozentsveig,&nbsp;Nadezhda M. Vitkovskaya","doi":"10.1002/poc.4515","DOIUrl":"10.1002/poc.4515","url":null,"abstract":"<p>The reactivity of bis(2-chloroprop-2-enyl)sulfide in the system hydrazine hydrate/alkali has been studied using quantum-chemical methods. The B2PLYP-D2//B3LYP approach shows a good agreement between the relative values of activation barriers compared to high-precision CBS//Q-B3. The correction for the entropy change during the transition from the gas phase to the binary solvent hydrazine hydrate is calculated. The IEF PCM model was parameterized for hydrazine hydrate solvent. The studied reaction routes includes (i) a competition between migration of the C=C bond and dehydrochlorination of bis(2-chloroprop-2-enyl)sulfide; (ii) 1,3-prototropic rearrangements of bis (allenyl)sulfide resulting from a dehydrochlorination; (iii) the possible substitution of sulfur and chlorine atoms with hydrazine. The probable formation of the thiiranium and thiirenium cations formation in the above has also been evaluated.</p>","PeriodicalId":16829,"journal":{"name":"Journal of Physical Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":1.8,"publicationDate":"2023-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48704728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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