Spin and charge interactions between nanographene host and ferrocene

• Akira Suzuki,
• Yuya Miyake,
• Ryoga Shibata and
• Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

• increment of screening effect on photoemission hole by increasing in conduction electrons. Increasing in conduction π electron of nanographene in FeCp2-ACFs-150 suggests the charge transfer from FeCp2 to ACFs. In this connection, the observed partial ionization of FeCp2 is well understood by the structure

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• ). Samples were ionized by electron impact ionization (EI) on an Agilent 6890/5973 or Agilent 7890/5977 GC–MS equipped with a HP-5 capillary column using helium carrier gas or by electron spray ionization (ESI) on an Agilent 1200/6210 time-of-flight (TOF) LC–MS. X-ray single-crystal structure analysis was

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• , 4.6 × 150 mm) and connected to an Agilent 6230 TOF mass spectrometer with electrospray ionization (ESI). Analyses used an isocratic mixture containing 65% water, 25% acetonitrile, and 10% isopropanol at a flow rate of 0.5 mL/min. The mass spectrometer was run in the negative ion mode with a probe

Enhanced reactivity of Li⁺@C₆₀ toward thermal [2 + 2] cycloaddition by encapsulated Li⁺ Lewis acid

• Hiroshi Ueno,
• Yu Yamazaki,
• Hiroshi Okada,
• Fuminori Misaizu,
• Ken Kokubo and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2024, 20, 653–660, doi:10.3762/bjoc.20.58

• mode high-resolution matrix-assisted laser desorption ionization mass spectra showed the formation of the monoadducts at m/z 875.10431 (5a) and 861.08866 (5b), which were assigned to each molecular ion ([M]+ calcd for C70H12OLi (5a): 875.10427 and C69H10OLi (5b): 861.08862, respectively). The UV–vis

• , external standard), and carbon of the solvent for 13C (53.84 ppm, CD2Cl2). High-resolution matrix-assisted laser desorption ionization (HR-MALDI) mass spectra were obtained on a Bruker solariX 12T mass spectrometer with dithranol as a matrix. UV–vis absorption spectra were measured on a JASCO V-670 and a

Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• ™ Impact instrument (electrospray ionization). Melting points were determined on a Fisher–Johns melting point apparatus. X-ray diffraction study The X-ray diffraction dataset of compound 3b was recorded on an Agilent SuperNova diffractometer using a microfocus X-ray radiation source with copper anode and

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• was concentrated in vacuo to yield 1 (7.9 mg). LC–MS analysis Electrospray ionization-mass spectrometry (ESIMS) data was collected using a Triple TOF 5600+ LC–MS/MS System (AB Sciex, Framingham, MA, USA) with an ODS column (Capcell Core C18, 3.0 i.d. × 100 mm, 40 °C) (Osaka Soda, Japan) at a flow rate

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• Maxis™ Impact (resolving power (FWHM) of 40,000 at m/z 1222, electrospray ionization). The cyclic voltammograms of 4a–h, 5a–c, 6a,b, and 10c were measured with the use of three-electrode configuration (glassy carbon working electrode, Pt counter electrode, Ag/Ag+ reference electrode using 0.01 M AgNO3

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

• Sharmila Neupane,
• Marcelo Rodrigues de Amorim and
• Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

• for MS2 scan survey. Precursor ion was impacted with three different collision energies (33, 45, 57 V), and the resulting MS2 spectra were combined into one final MS2 spectrum. The mass spectra were acquired using Turbo Spray Ionization set to 5.5 kV in positive ion mode with an accumulation time of

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• be associated with the increased basicity of the starting substrate and its structural organization (proximity of the two nitrogen atoms). The revealed inertness may also be rationalized via the ionization of the starting dipyridoacenaphthene system 5 to an anion or even dianion 7 (at least in

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• lifetimes, radiative and non-radiative relaxation pathways of the indigo chromophore [26][27][30][31][32][33][34][35] as well as to estimate ionization potentials and electronic structures [28][29], singlet oxygen generation capacity [31], QSAR properties [25], and others. In both solution and solid state

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• CFCl3 (δF 0.0). Assignments of the signals in the NMR spectra were performed using 2D-spectroscopy (COSY, HSQC, HMBC) and DEPT-135 experiments. For the copies of NMR spectra for all new compounds see Supporting Information File 1. High resolution mass spectra (electrospray ionization, HRESIMS) were

Electron-beam-promoted fullerene dimerization in nanotubes: insights from DFT computations

• Laura Abella,
• Gerard Novell-Leruth,
• Josep M. Ricart,
• Josep M. Poblet and
• Antonio Rodríguez-Fortea

Beilstein J. Org. Chem. 2024, 20, 92–100, doi:10.3762/bjoc.20.10

• + C60 to assess the effect ionization produced by the electron beam has in the process. Before the reaction takes place, a stabilizing van der Waals complex between the two C60 molecules was formed (Figure 2), with an interdimer distance around 3 Å (slightly larger for the neutral profile). For dimer 1

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• and evaporated completely in vacuo. The residual materials were dissolved in 200 µL of methanol. The obtained samples were analyzed by liquid chromatography–electrospray ionization mass spectrometry (LC–ESIMS) using an LC-2040C 3D Plus system (Shimazu Corp., Kyoto, Japan) equipped with a COSMOCORE

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• of the compounds are sensitive to the medium. Cyclic voltammetry measurements indicate good hole-blocking and electron-injecting properties due to their high ionization potentials. Photoelectron spectroscopy and time-of-flight measurements reveal good electron-transporting properties for one of the

• results of CV measurements were used to obtain the ionization potential (IPCV) and electron affinity (EACV) values of the compounds 6–9. These values were obtained using the following equations: IPCV = e (Eonset,red − Fconset + 4.8), EACV = e (Eonset,ox − Fconset + 4.8) [7]. The IPCV values fall in a

• range of 5.80–5.90 eV, while the electron affinities (EACV) vary from 3.20 to 3.33 eV (Table 1). The obtained values are comparable to the corresponding ionization potentials (IPPE) and electron affinities (EAPE) obtained for the films by photoelectron emission spectrometry, presented and discussed in

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• , such as alkyl halides. In this study, the thermal reaction of the La@C2v-C82 anion with benzyl bromide derivatives 1 at 110 °C afforded single-bonded adducts 2–5 with high regioselectivity. The products were characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

• -electron reduction of Gd@C2v-C82 for the addition reaction to occur at room temperature [22]. Supporting Information File 1, Figure S1 depicts the three HPLC separation steps including recycling for the isolation. The matrix-assisted laser desorption/ionization time-of-flight (MALDI–TOF) mass spectra of 2a

• reduction of La@C2v-C82 is an easy and effective method for controlling its reactivity and selectivity via ionization for the production of La@C2v-C82 derivatives. Experimental General: All chemicals and solvents were obtained from Wako, TCI, and Aldrich and were used without further purification unless

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

• Recep Isci and
• Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

• (OFETs) [26][27][28], capacitors [29][30], hybrid films [31], and photosensitizers [32][33][34]. Another important π-conjugated unit is triphenylamine (TPA), having an ionization potential of 6.80 eV, which is lower compared to many other organic cores, thus providing a strong electron-donating ability

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• reaction mechanism of the presented method was studied on model reactions by electrospray-ionization time-of-flight (HRESI–TOF) mass spectral analysis in a timely manner. The analytical results indicated that the observed azafulvene-ended di- and tripyrrolic intermediates are responsible for the formation

• product formation, mass spectral analyses of model reactions were investigated by time-dependent electrospray-ionization time-of-flight (HRESI–TOF) technique. Results and Discussion Reactions of meso-pentafluorophenyl-substituted A2-tripyrrane 1 and N-tosylimines 2 were performed in the presence of Cu(OTf

• certain time intervals within 2 hours and examined by ESI LC–MS. Throughout the high-resolution electrospray-ionization time-of-flight (HRESI–TOF) mass analysis of the reaction mixture at 0 °C, the following peaks were observed: m/z = 246.0366 ([M + H]+ calcd for C11H5F5N, 246.0337), m/z = 857.1468 ([M

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• ionization. HPLC–MS was performed on an HPLC system using a Shimadzu LCMS-2020 (Shimadzu Corp., Japan) device equipped with a Reprospher (Altmann Analytik Corp., Germany) 100 Å C18 (5 µm; 100 × 3 mm) column and a positive/negative double ion source with a quadrupole MS analyzer in the range of 50–1000 m/z

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• otherwise specified. Gaseous products were determined by a gas chromatograph equipped with two barrier discharge ionization detectors (GC–BID). Typically, the concentrations used for the first screening were: 1 mM for PS, 0.1 mM for catalyst 1, and 20 mM for BIH, and the bases used were either

• from Shimadzu (GC-2030) equipped with two barrier discharge ionization detectors (BID). Every test was repeated at least twice. The photon flux was evaluated with actinometry, according to a previously published procedure [42], and it was 0.025 µE s−1. Therefore, an apparent photoluminescent quantum

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• wide range of semiconductors, they must exhibit low ionization energies and thus air sensitivity. One approach to circumvent this issue is to identify systems where the electron-transfer process is coupled to other chemical reactions, increasing the kinetic stability of the dopant to air, and thus

• their Y = cyclohexyl counterparts, 1e+/1e• and 1h+/1h•, respectively. These differences are also similar to those previously seen in the comparison of Y = metallocenyl systems 1c+/1c• and 1d+/1d• with 1e+/1e• (and in the DFT-calculated ionization energies of 1c–e•) [14][50] and are perhaps surprising

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• electrospray ionization HRESIMS analysis, and quantum chemical electronic CD calculations. Furthermore, the absolute configurations of sugar residues were determined by derivatization of the hydrolysates with ʟ-cysteine methyl ester and o-tolyl isothiocyanate followed by HPLC analysis. The anti-inflammatory

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• , emitted from the surface of polymers [178]. When a high-energy photon impacts an atomic electron, part of the photon energy is transferred to the electron leading to excitation or ionization and radical formation, and a deflected photon with lower energy is emitted, ready to impact another electron. This

Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea

• Winnie Chemutai Sum,
• Sherif S. Ebada,
• Didsanutda Gonkhom,
• Cony Decock,
• Rémy Bertrand Teponno,
• Josphat Clement Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84

• speed ETD ion trap mass spectrometer (Bruker Daltonics, Bremen, Germany) for HPLC-DAD/MS in positive and negative ionization modes. The HPLC (Dionex UltiMate 3000 UHPLC, Thermo Fisher Scientific Inc., Waltham, MA, USA) system’s stationary phase was composed of a C18 Acquity UPLC BEH column (Waters

• at 0.6 mL/min and the UV–vis detection made at 210 nm and 190–600 nm. The isolates were analyzed on a MaXis ESI-TOF (time-of-flight) mass spectrometer (Bruker Daltonics) for the HRESIMS data, in the positive ionization mode. This was coupled to an Agilent 1260 series HPLC–UV system (Agilent

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO₂F₂)

• Xian-Lin Chen and
• Hua-Li Qin

Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68

• nitriles 3ba–da in excellent yields. Interestingly, when the loading of CH3COOK was reduced to 2 equivalents, we obtained a mixture of unsaturated nitrile 3aa and saturated nitrile 4 after column chromatography (Scheme 4). We speculated that the reduction of the base equivalent may induce the ionization of

Recommendations for performing measurements of apparent equilibrium constants of enzyme-catalyzed reactions and for reporting the results of these measurements

• Robert N. Goldberg,
• Robert T. Giessmann,
• Peter J. Halling,
• Carsten Kettner and
• Hans V. Westerhoff

Beilstein J. Org. Chem. 2023, 19, 303–316, doi:10.3762/bjoc.19.26

• has occurred at a microscopic level and from both directions of reaction. Binding, ionization, and reactions that involve the formation of complexes often proceed rapidly. In such cases, the assumption is generally made that equilibrium has been achieved. In any case, any assumption regarding the