Two-fold addition reaction of silylene to C₆₀: structural and electronic properties of a bis-adduct

• Masahiro Kako,
• Masato Kai,
• Masanori Yasui,
• Michio Yamada,
• Yutaka Maeda and
• Takeshi Akasaka

Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100

• C60 and quaternary carbons of the Dip groups are indicated by grey circles. ORTEP drawing of 3 showing thermal ellipsoids at the 50% probability level at 100 K. Hydrogen atoms are omitted for clarity. (a) Partial structures of isomers of Dip2SiC60. (b) Optimized structures of 2a and 2c. Hydrogen atoms

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

• Vladislav V. Nikol’skiy,
• Mikhail E. Minyaev,
• Maxim A. Bastrakov and
• Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

• molecule is not shown), 13c (top right), and 13d (bottom) with thermal ellipsoids set at a 50% probability level. Intermolecular hydrogen bonds are drawn with dashed lines. Methods for the synthesis of isoxazolo[4,5-b]pyridines: (A) annulation of an isoxazole fragment to a pyridine ring; (B) annulation of

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

• molecules within and between a layer with two molecules at the top and the bottom of the unit cell. b) Determined from X-ray structural analysis at 123 K. Element color: carbon (grey), hydrogen (white), oxygen (red) and nitrogen (blue). The thermal ellipsoids are drawn at the 50% probability level. UV–vis

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

• Andrew D. Gillie,
• Matthew G. Wakeling,
• Bethan L. Greene,
• Louise Male and
• Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

• complexes from 6a. The single crystal X-ray diffraction structures of 13 and 14 have ellipsoids drawn at 50% probability, with hydrogens and solvent omitted for clarity. Selected bond angles and distances: 13: C1–Au: 1.98 Å, Au–Cl: 2.28 Å, N2–Au: 3.65 Å. N1–C1–N3: 102.7°, N3–C1–Au: 129.5°, N1–C1–Au: 127.1

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• important. A selective hydration of the polar moiety while keeping the pyrene moiety stable can relatively strengthen the stability of conformation 2. Thus, as the polarity of the solvent increases, the probability of conformation 2 appearance is expected to increase. Mechanism of bi-stability in PASE on

• II. Thus, as the polarity of the solvent increases, the probability of the appearance of conformation II is expected to increase. Then, conditions of the temperature and the external pressure of gases have to be chosen properly, too. We need to keep the pyrene part stable in the whole procedures

• increase in the probability that the active center of the antigen/antibody reaction reacts with the antigen. To realize a good temperature condition, the barrier height should be close to or even less than 0.3 eV. Reducing the barrier height may be achieved by optimizing the solution to achieve nearly

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

• of compound 2b in acetonitrile before (1) and after 15 s (2), 35 s (3), 75 s (4), 2.5 min (5) and 5 min (6) of irradiation with light of 436 nm (c 5.0 × 10−5 mol·L−1). Molecular structure of O-acylated isomer 3b. Thermal ellipsoids are drawn at the 50% probability level. Fragment of the molecular

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• . Key 1H-1H COSY (bond lines), and HMBC (red arrows) correlations of 1–3. NOE correlations of compounds 1 and 2 (solid line indicates β-orientation and dashed lines represent α-orientation). X-ray crystal structure of compounds 1–3 (with a thermal ellipsoid probability of 50%). Proposed biosynthetic

Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• sp2 carbon of [10]CPP within 0.30 nm. HOMO−1, HOMO, LUMO, and LUMO+1 orbitals of [10]CPP⊃[5]CPP2+ (1), [5]CPP2+, and [10]CPP. X-ray crystal structure of [10]CPP⊃[5]CPP2+[B(C6F5)4]2. a) Side and b) top views of ORTEP drawings. The thermal ellipsoids are scaled at the 50% probability level. All hydrogen

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

• , Supporting Information File 1. Thermal ellipsoids are drawn at the 50% probability level. UV–vis spectra of 6,8-di-tert-butyl-2-(arylamino)-3H-phenoxazin-3-ones 4a–h (toluene, c = 2⋅10−5 M, l = 1 cm, T = 293 K). Molecular structure of ethyl 2,4-di-tert-butyl-14H-quinoxalino[2,3-b]phenoxazine-10-carboxylate

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• ) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent conformation. Thermal ellipsoids are shown at the 50% probability level, and all hydrogen atoms as well as propyl groups on imide substituents have been omitted for clarity. Reprinted with permission from [57]. Copyright

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

• measurement of the quartz standards (to monitor the instrument stability). Each measurement at a particular concentration was repeated 10 times, then averaged and plotted against concentration. The standard deviations were calculated by using the Student’s distribution (95% probability) and did not exceed 1

• % unless specified otherwise, see the error bars; the error bar is on the order of the symbol size if not visible). The standard deviations were calculated by using the Student’s distribution (95% probability). The grey boxes in the figure are drawn to guide the eye and designate different ranges of

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

• Pengcheng Li,
• Daniel Kowalczyk,
• Johannes Liessem,
• Mohamed M. Elnagar,
• Dariusz Mitoraj,
• Radim Beranek and
• Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

• significance of the chosen parameters was evaluated by analysis of variance (ANOVA). The “Prob>F” probability value gives the estimation of whether the parameter has a significant effect on the response, and generally a parameter with a probability value less than 0.05 is considered as significant. A

• probability value larger than 0.10 renders the parameter generally as insignificant [35]. It is evident from Table 2 that light intensity and inert gas flow can be regarded as significant, while the photocatalyst amount and the stirring speed are insignificant. In addition to this analysis, it is necessary to

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• orbitals), the dianion has an additional 6π-aromatic cyclopentadienyl anion (highlighted in green), while the cation has a 6π-aromatic 1,3-dithiolium ring (highlighted in red). ORTEP plots (50% probability) and crystal packing of compounds a) 25, b) 26, and c) 29. The respective crystal packing of each

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

• Matthias R. Steiner,
• Max Schmallegger,
• Larissa Donner,
• Johann A. Hlina,
• Christoph Marschner,
• Judith Baumgartner and
• Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

• on the solid-state structure of 2a and the numbering scheme of the phenolate moiety. a) Molecular structure of 2a, hydrogen atoms omitted for clarity, thermal ellipsoids drawn at 30% probability level. Selected distances (Å) and angles (deg): P1–C6 = 1.758(2), P1–C15 = 1.824(2), P1–C18 = 1.814(2), P1

Long oligodeoxynucleotides: chemical synthesis, isolation via catching-by-polymerization, verification via sequencing, and gene expression demonstration

• Yipeng Yin,
• Reed Arneson,
• Alexander Apostle,
• Adikari M. D. N. Eriyagama,
• Komal Chillar,
• Emma Burke,
• Martina Jahfetson,
• Yinan Yuan and
• Shiyue Fang

Beilstein J. Org. Chem. 2023, 19, 1957–1965, doi:10.3762/bjoc.19.146

• -cyanoethyl groups were removed by flushing the CPG with a solution of DBU in ACN. Under these conditions, the ODN remains on CPG and the nucleobases remain protected, both of which decrease the probability of the Michael addition side reaction. After washing off acrylonitrile, the CPG was subjected to

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

• Nedra Touj,
• François Mazars,
• Guillermo Zaragoza and
• Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

• ) with thermal ellipsoids drawn at the 50% probability level. ORTEP representations of zwitterions 6b (MIC-Dip-Ph-Me·CS2, top) and 6e (MIC-Mes-Bu-Me·CS2, bottom) with thermal ellipsoids drawn at the 50% probability level. Synthesis of CAAC·CS2 zwitterion 2 from its free carbene parent 1. Synthesis of

Studying specificity in protein–glycosaminoglycan recognition with umbrella sampling

• Mateusz Marcisz,
• Sebastian Anila,
• Margrethe Gaardløs,
• Martin Zacharias and
• Sergey A. Samsonov

Beilstein J. Org. Chem. 2023, 19, 1933–1946, doi:10.3762/bjoc.19.144

• acidic FGF-ligand 3; Cα@Arg296-C3@12GlcA for cathepsin K-ligand 4. The reaction coordinate values increased in each subsequent window, with the starting point for each window taken from the previous one. The overlap between the probability distributions in adjacent windows was analyzed both using

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

• C14, C10, C18, and C9 in Ce@C2v-C82(CH2C6H3Me2), which is attributed to the 1b, 1d, 1c, and 1a isomers in [25]. The carbon atom numbers correspond to that shown in Figure 6d. ORTEP drawing of 3a with thermal ellipsoids shown at 50% probability level. Only an independent unit of 3a is shown. This

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• GalN as well as 8 other molecules. For benchmarking purposes, all spectra were annotated with true labels. By running the model inference for one spectrum multiple times we can measure the variability of its prediction probability for each category. If the model gives consistently a high probability

• for one category after each inference, then its uncertainty is low, and the spectrum likely belongs to the said category of molecules. On the other hand, if the model predicts a category with highly variable probability, then the uncertainty is high, and the spectrum likely does not belong to any of

• the classification categories. We ran model inference 200 times on each sample and obtained the mean prediction probability for every category as its variability represented by the interpercentile range 5 to 95%. The results are shown in Figure 5. As an example: the spectrum of CS-C is predicted as

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

• drawing of crystal polymorph 1a (left) and 1b (right), shown at the 50% probability level. Hydrogen atoms and co-crystallized solvent molecules are omitted for clarity. UV–vis absorbance of complex 1 in DMA. Inset: zoom-in of the 500–800 nm range to visualize the low-intensity bands associated with metal

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• structure was calculated with the Pymol tool [66]. ORTEP representation of the new N-acylhydrazones synthesized in the present work, drawn with thermal ellipsoids at 30% probability. Left: hdz-CH3 and right: hdz-NO2. (A) Superposition of molecular structures and stacked motifs of (B) hdz-CH3 and (C) hdz-NO2

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• may also enhance the rISC in OLED devices, in which the electron–hole recombination produces mainly the triplet state (the theoretical probability is 75%, by following the spin statistic rule) [1]. Compared to the application studies, the investigation of the photophysical mechanism of TADF emitters

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• PCM/mPW1PW91/6-311+G(d,p) [16] level for (7R*,10S*)-1 (1a) and (7S*,10S*)-1 (1b), which are possible diastereomers of 1. The results reveal that 1a has the highest probability score. Next, ECD calculations on (7R,10S)-1 and (7S,10R)-1 were conducted according to the results obtained from NMR

• configurations of chiral centers in 3 apart from C-11 were assigned. To determine the configuration of C-11 we performed NMR calculations. The results disclose that 3 has likely the configuration of (7R*,10R*,11S*)-3 based on the DP4+ probability analysis and the correlation coefficient. To clarify the absolute

• configuration of 5 was assigned as (7R*,10R*,11S*)-5 by conducting NMR calculations at the PCM/mPW1PW91/6-311+G(d,p) level, calculated for (7S*,10S*,11S*)-5 (5a) and (7R*,10R*,11S*)-5 (5b) using the correlation coefficient and DP4+ probability analysis. The absolute configuration of 5 was subsequently assigned

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

• ellipsoid contour probability level of 50%; edetected by GC–MS. The acid-catalyzed reversible transformation of tetrahydrofuro[3,2-c]pyridine 4a and 3-(2-oxopropyl)piperidin-4-one 5a. The product yield was determined by GC–MS using an internal standard. Synthesis of tetrahydropyrrolo[3,2-c]pyridine 6a