Synthesis and uranyl(VI) extraction performance of a calix[4]pyrrole–tetrahydroxamic acid receptor

• Sara Karnib,
• Rana Baydoun,
• Wissam Zaidan,
• Nancy AlHaddad,
• Omar El Samad,
• Bilal Nsouli,
• Francine Cazier-Dennin and
• Pierre-Edouard Danjou

Beilstein J. Org. Chem. 2026, 22, 486–494, doi:10.3762/bjoc.22.36

• relevant example is a calix[6]arene functionalized with three hydroxamic acid groups, where a theoretical study using density functional theory (DFT) calculations showed that the complex with the uranyl is most stabilized when only two of the three hydroxamic acid units participate in binding [78]. This

Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene

• Yukiho Hashimoto,
• Yuuya Kawasaki,
• Kazunobu Igawa and
• Katsuhiko Tomooka

Beilstein J. Org. Chem. 2026, 22, 436–442, doi:10.3762/bjoc.22.30

• . The CD spectrum of 1ab showed a weak positive Cotton effect around 270 nm and a strong Cotton effect around 230 nm, and that of 1ad showed a weak negative Cotton effect around 290 nm and a strong Cotton effect around 250 nm. Each TD-DFT calculations for (R)-1ab and (R)-1ad showed good agreement in

• : 254 nm): a1), a2) chromatograms monitored at 254 nm; b1), b2) CD spectrum of the first eluates in a flow cell; c1), c2) calculated CD spectra using TD-DFT calculations at the B3LYP level using the 6-311G(2d,2p) basis set for C, H, and O atoms and the SDD basis set with the corresponding effective core

• procedures, characterization data, copies of 1H and 13C NMR spectra, and optimized geometries of DFT calculations. Supporting Information File 26: Crystallographic information file of compound 1ac. Acknowledgements We thank K. Imamura (Evaluation center of material properties, IMCE Kyushu University) for

Synthesis and anti-cancer activity of naphthalimide–organylselanyl conjugates

• Rajkumar Ravi and
• Selvakumar Karuthapandi

Beilstein J. Org. Chem. 2026, 22, 416–435, doi:10.3762/bjoc.22.29

• analyses, and structure and electronic properties were further investigated using density functional theory (DFT) calculations. Cytotoxicity tests were used to assess the anticancer potential of both conjugates, and it was found that both compounds showed notable activity against the test MDA-MB-231 breast

Electrosynthetic access to unsymmetrical oxaza[8]helicenes with high chiral stability and strong circularly polarized luminescence (CPL)

• Tin Zar Aye,
• Rubal Sharma,
• Muthu Karuppasamy,
• Daiya Suzuki,
• Haruka Nakajima,
• Yoshitane Imai,
• Mitsuhiro Arisawa,
• Mohamed S. H. Salem and
• Shinobu Takizawa

Beilstein J. Org. Chem. 2026, 22, 372–382, doi:10.3762/bjoc.22.25

• products were detected under the optimized conditions (Scheme 2). Based on our previous reports [48][56], DFT calculations, and cyclic voltammetry (CV) analyses (Figure 1), anodic single-electron transfer (SET) is expected to occur first from 3, generating the electrophilic radical cation [3]·+ as 3 (Eox

• [8]helicenes 5a and 5b, we performed DFT calculations to locate the transition states with the highest Gibbs free energies. In both cases, the transition states correspond to conformations in which the terminal rings adopt a face-to-face arrangement along the helical axis (Figure 3). The calculated

• insight into the electronic transitions, we performed time-dependent DFT (TD-DFT) calculations for all oxaza[7]helicenes 6 and oxaza[8]helicenes 5 after geometry optimization at the S1 minimum (see Supporting Information File 1 and Supporting Information File 2) [62][63]. The convergence of these

Recent advances in the cleavage of non-activated amides

• Eun-Sol Choi and
• Hyo-Jun Lee

Beilstein J. Org. Chem. 2026, 22, 352–369, doi:10.3762/bjoc.22.23

• restored after recalcination prior to reuse. Based on DFT calculations, the authors proposed that octanol is deprotonated and coordinated to Ce, while the amide substrate is simultaneously activated electrophilically through coordination to the Ce center (A). This dual activation enables the lattice oxygen

• transition-metal-catalyzed asymmetric C–H activation reactions as a directing group, thus necessitating an efficient method for the cleavage of 8-aminoquinoline-derived amides. The role of Me2SO4 in this transformation was elucidated through DFT calculations. Methylation of the carbonyl oxygen by Me2SO4

• bioactive compounds underwent smooth esterification with TFE to give the corresponding 2,2,2-trifluoroethyl esters 82–85 in high yields. To elucidate the reaction mechanism, cyclic voltammetry experiments, control reactions, and DFT calculations were conducted. At the anode, bromide ions are oxidized to

Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

• Arthur A. Puzyrkov,
• Andrew S. Drachuk,
• Ekaterina A. Popova,
• Alexander V. Stepakov and
• Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

• formation of azomethine ylide from alloxan (1) and ʟ-proline (2) was previously studied using DFT calculations [43]. Based on the calculated data, it was assumed that the 1,3-dipole is formed as a result of a multistage sequence: initial generation of a zwitterionic imine intermediate from 1 and 2, followed

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

• Adrian G. Rossebø,
• Hannah G. Kolberg,
• Anders E. Tønder,
• Louise Kjaerulff,
• Poul Erik Hansen,
• Karla A. Frydenvang,
• Jesper Østergaard and
• Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

• be partially responsible for its high membrane permeability. To investigate if an IMHB is indeed present in 1, we combined DFT calculations with NMR spectroscopy titrations. For a system containing an IMHB, it would be expected that replacing the proton (O–H) with a deuteron (O–D) would lead to an

• isotope effect observable as changes in the 13C NMR chemical shift [18][19]. DFT calculations were based on a truncated model (Figure 6a) containing the essential elements for intramolecular hydrogen bonding. The structure was considered both in vacuum as well as with DMSO or water as implicit solvents

• and 0.1% phosphoric acid in the ratios 35:65 and 25:75, v/v for the distribution coefficient and stability experiments, respectively. The ChemStation software (Version B.04.03, Agilent Technologies) was used for instrument control and data collection. Computational chemistry DFT calculations were

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

• Daiki Tauchi,
• Sota Ogura,
• Misa Sakura,
• Kazunori Tsubaki and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

• chiral platinum(II) complex was synthesized via Sonogashira coupling and subsequent coordination of a pincer ligand to a precursor. The complex exhibited a broad absorption band ranging from 250 to 550 nm in the UV–vis spectrum, with TD-DFT calculations indicating mixed ligand-to-ligand charge transfer

• behavior, through a combination of experimental measurements and density functional theory (DFT) calculations. The experimental UV–vis spectrum was in good agreement with the DFT calculations, revealing that the electronic transitions originate from both ligand-to-ligand charge transfer (LL’CT) and metal

• spectroscopy, as well as high-resolution mass spectrometry (HRMS). Due to its low solubility, single crystals suitable for X-ray crystallographic analysis could not be obtained. Spectroscopic analysis and DFT calculations To elucidate the electronic structure of the platinum(II) complex, UV–vis absorption

Symmetrical D–π–A–π–D indanone dyes: a new design for nonlinear optics and cyanide detection

• Ergin Keleş,
• Alberto Barsella,
• Nurgül Seferoğlu,
• Zeynel Seferoğlu and
• Burcu Aydıner

Beilstein J. Org. Chem. 2026, 22, 131–142, doi:10.3762/bjoc.22.6

• cyanide and the chemosensor is determined by a 1H NMR study and explained by DFT calculations. Keywords: chemosensor; DFT calculations; donor–π–acceptor–π–donor based organic dyes; indan-2-one; NLO; Introduction Over the past decades, the functional heterocyclic push–pull dyes have attracted significant

• functional theory (DFT) and time-dependent DFT (TD-DFT) calculations, which were consistent with experimental results. NLO properties of the compounds were experimentally determined using the EFISH method and calculated using theoretical methods. Additionally, the thermal decomposition temperatures, an

• spectrometry methods (Figures S1–S10 in Supporting Information File 1). Optical properties of dyes Photophysical properties of dyes 2a–c were assessed in four different organic solvents with various polarities (DMSO, acetone, chloroform, and THF) via absorption spectra and DFT calculations (Table 2). Figure 2a

Advances in Zr-mediated radical transformations and applications to total synthesis

• Hiroshige Ogawa and
• Hugh Nakamura

Beilstein J. Org. Chem. 2026, 22, 71–87, doi:10.3762/bjoc.22.3

• for the success of the reaction. DFT calculations suggested that in the transition state (TS1), a Cl–π interaction between the chlorine atom on the zirconocene catalyst and the aromatic ring of the substrate facilitated rapid halogen atom transfer (XAT), generating a radical at the C3 position of

• potential and stabilizing the radical pathway. The DFT calculations are shown in Scheme 13A. The activation barrier for the XAT process was calculated to be ΔG‡ = 8.0 kcal/mol, indicating that this process can proceed spontaneously around room temperature. Moreover, the transition state (TS1) suggested the

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

• Alexander S. Budnikov,
• Nikita E. Leonov,
• Michael S. Klenov,
• Andrey A. Kulikov,
• Igor B. Krylov,
• Timofey A. Kudryashev,
• Aleksandr M. Churakov,
• Alexander O. Terent’ev and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

• end of the reaction), which is sufficient to oxidize ADN. According to the performed calculations, competitive oxidation of 1a does not occur, which is confirmed by the obtained CV-data (see Figure 1 and Figure 2). According to DFT calculations, the reaction of N-radical A with 2-nitro-2

Recent advancements in the synthesis of Veratrum alkaloids

• Morwenna Mögel,
• David Berger and
• Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

• -NOESY and DFT calculations. The tertiary amine was masked as the hydrochloride salt with concomitant ketal deprotection, which was followed by hydrogenation to remove the benzyl protecting group to obtain (±)-4-methylenegermine hydrochloride (17·HCl) in 31 steps (LLS from commercial materials) and an

Recent advances in total synthesis of illisimonin A

• Juan Huang and
• Ming Yang

Beilstein J. Org. Chem. 2025, 21, 2571–2583, doi:10.3762/bjoc.21.199

• . However, subsequent density functional theory (DFT) calculations by the Tantillo group on rearrangements of potential biosynthetic precursors revealed that structure 10 corresponds to a transition state rather than a stable intermediate of the 1,2-alkyl migration [27]. Their study further indicated that

Synthesis of the tetracyclic skeleton of Aspidosperma alkaloids via PET-initiated cationic radical-derived interrupted [2 + 2]/retro-Mannich reaction

• Ru-Dong Liu,
• Jian-Yu Long,
• Zhi-Lin Song,
• Zhen Yang and
• Zhong-Chao Zhang

Beilstein J. Org. Chem. 2025, 21, 2470–2478, doi:10.3762/bjoc.21.189

• of new reactions and strategies. In this work, a PET-initiated cationic radical-derived interrupted [2 + 2]/retro-Mannich reaction of N-substituted cyclobutenone provided a facile approach to the direct construction of the ABCE tetracyclic framework of Aspidosperma alkaloids. DFT calculations showed

Catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formations

• Qi-Sen Gao,
• Zheng-Wei Wei and
• Zhi-Min Chen

Beilstein J. Org. Chem. 2025, 21, 2447–2455, doi:10.3762/bjoc.21.186

• excellent conversion rates (up to 95% yield) and high enantioselectivity (up to 96% ee). Notably, isoquinoline derivatives containing polycyclic naphthalene moieties or ortho-substituted phenyl groups also demonstrated good reactivity and compatibility. DFT calculations indicated that the C–Se bond

• products demonstrated complete E-stereoselectivity (E/Z ratio >20:1). Notably, under the same reaction conditions, aliphatic selenols remained unreactive. Density functional theory (DFT) calculations revealed that the rate-determining step involves the nucleophilic attack of the selenium anion in

Pathway economy in cyclization of 1,n-enynes

• Hezhen Han,
• Wenjie Mao,
• Bin Lin,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2025, 21, 2260–2282, doi:10.3762/bjoc.21.173

• product 49 (Scheme 11, path a). When aryl or alkyl substituents were introduced on the alkyne moiety, a more stable vinylidene intermediate 50 was formed via a 6-endo-dig cyclization, ultimately leading to the generation of the bicyclo[3.3.1]nonadiene product 51 (Scheme 11, path b). DFT calculations

• cleavage to form the boronated phenanthrene framework 170. It is worth mentioning that a unique skeleton rearrangement, supported by DFT calculations, was proposed in this work, which was unprecedented in BiCl3-promoted cyclization. Conclusion This comprehensive review has systematically delineated the

A m-quaterphenyl probe for absolute configurational assignments of primary and secondary amines

• Yuka Takeuchi,
• Mutsumi Kobayashi,
• Yuuka Gotoh,
• Mari Ikeda,
• Yoichi Habata,
• Tomohiko Shirai and
• Shunsuke Kuwahara

Beilstein J. Org. Chem. 2025, 21, 2211–2219, doi:10.3762/bjoc.21.168

• conformers, obtained via DFT calculations, show a correlation with both the sign and intensity of the experimentally observed CD spectra. Keywords: absolute configuration; chiral amine; chiral quaternary ammonium salt; circular dichroism; DFT calculation; Introduction Determining the absolute

Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings

• Lifen Peng,
• Ting Wang,
• Zhiwen Yuan,
• Bin Li,
• Zilong Tang,
• Xirong Liu,
• Hui Li,
• Guofang Jiang,
• Chunling Zeng,
• Henry N. C. Wong and
• Xiao-Shui Peng

Beilstein J. Org. Chem. 2025, 21, 2173–2201, doi:10.3762/bjoc.21.166

• mixture of propargyl alcohol 50 (0.7 mmol), NaN3 (2.8 mmol), n-Bu4NI (0.5 mmol) and MeCN (10 mL) under electrolysis (graphite rod as anode, stainless-steel plate as cathode, 11 mA) at rt for 10 h. According to the experimental results and density functional theory (DFT) calculations, a plausible mechanism

Understanding the origin of stereoselectivity in the photochemical denitrogenation of 2,3-diazabicyclo[2.2.1]heptene and its derivatives with non-adiabatic molecular dynamics

• Leticia A. Gomes and
• Steven A. Lopez

Beilstein J. Org. Chem. 2025, 21, 2007–2020, doi:10.3762/bjoc.21.156

• TD-DFT calculations were performed using the range-separated hybrid density functional ωB97X-D [89] with the aug-cc-pVTZ [90][104] basis set. All single reference methods were run using the Gaussian 16 software [105]. Multiconfigurational methods The multiconfigurational calculations were performed

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• density functional theory (DFT) calculations were obtained. Results and Discussion Photoreduction of 2-benzoylimidazolium triflate with diisopropylethylamine Initial investigations To investigate the potential for the light-mediated reduction of acylazolium salts, compound 1 was prepared as a

• , however, did not reveal any significant change in the absorption profile. To gain further insight, time-dependent density functional theory (TD-DFT) calculations were carried out (for details of the computational studies, see Supporting Information File 1). In line with the UV–vis studies, comparison of

• ][26][27][28][29][30]. The TD-DFT calculations also provided insight into the nature of the subsequent mechanistic steps where the excited benzoylimidazolium 1* is converted to the reduced zwitterionic alkoxide species E in the presence of DIPEA (Scheme 2). This requires the transfer of both an

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• process hazards through the evaluation of thermal safety parameters and DFT calculations revealed catalytic and solvent effects of ionic liquids in nitration [9]. In addition, researchers have focused on improving nitration processes through process intensification strategies by integrating advanced

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

• Natalia Lebedeva,
• Fedor Kliuev,
• Olesya Zvereva,
• Klim Biriukov,
• Evgeniya Podyacheva,
• Maria Godovikova,
• Oleg I. Afanasyev and
• Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

• . The remedy for Parkinson’s disease, piribedil, was obtained in high yield. The plausible mechanism of the elaborated process was proposed and supported by DFT calculations. Keywords: amines; DFT; hypophosphites; reductive amination; role of cations; Introduction Sodium hypophosphite, NaH2PO2, is one

• the DFT calculations (Scheme 5, Figure 2). Firstly, reductive amination of an aldehyde started from a nucleophilic addition of the amine to the carbonyl group of the aldehyde. In the presence of acid, this step could occur via acidic catalysis involving a protonation step of an amine (Step_2) or

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• cyclization of functionalized phenyl isocyanides, guided by DFT calculations (Scheme 2b) [29]. Three types of isocyanides (10–12) were evaluated in reactions with aryl iodides, affording indole-fused N-heteroaryl scaffolds 13–15, featuring either a C–C or C–N stereogenic axis, in moderate-to-high yields with

• identified. While the employment of L9 afforded endo-selective [3 + 2] cycloadducts 60, using Trost ligand L10 resulted in a complete reversal to the exo-cycloadducts 61. DFT calculations were performed and indicated that these two ligands act in different ways in the cyclization process, providing

Synthesis of optically active folded cyclic dimers and trimers

• Ena Kumamoto,
• Kana Ogawa,
• Kazunori Okamoto and
• Yasuhiro Morisaki

Beilstein J. Org. Chem. 2025, 21, 1603–1612, doi:10.3762/bjoc.21.124

• spectra were simulated by time-dependent density functional theory (TD-DFT) calculations (TD-MN15/6-31G(d)//MN15/6-31G(d). The calculated rotatory strengths of (Sp)-6 and (Sp)-7 were plotted with their observed CD spectra in Figure 3A and 3B, respectively, and the calculated CD spectra are shown in

• ). Molecular orbitals of (Sp)-6 and (Sp)-7 in their ground and excited states were calculated using DFT and TD-DFT calculations (Figures S20–S23, Supporting Information File 1). In both molecules, the orbitals were localized to part of the π-conjugation systems rather than the whole system in the ground and

• excited states due to the twisted structures by the π-stacked [2.2]paracyclophane moieties. The CPL behaviors of (Sp)-6 and (Sp)-7 were investigated by TD-DFT calculations; namely, the electric transition dipole moment (μ), magnetic transition dipole moment (m), and the angle (θ) between μ and m in the S1

Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads

• Issei Fukunaga,
• Shunsuke Kobashi,
• Yuki Nagai,
• Hiroki Horita,
• Hiromitsu Maeda and
• Yoichi Kobayashi

Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121

• synthesized and characterized (Figure 1). Their photophysical properties were comprehensively examined by steady-state and time-resolved emission and absorption spectroscopy. Furthermore, time-dependent density functional theory (TD-DFT) calculations were performed to support the experimental findings

• shown in Supporting Information File 1. Energy levels and steady-state optical properties Time-dependent density functional theory (TD-DFT) calculations were performed to gain insights into the electronic structures of Pe–PTZ derivatives at B3LYP/6-31+G(d,p) level of theory (Figure 2) [18]. The

• absorption bands derived from the Pe moiety between 390 and 450 nm. A broad absorption feature around 320 nm, whose intensity increased with the number of TPA groups, was also observed. The increase in the absorption with the increase in the number of TPA groups is reproduced by TD-DFT calculations (Figure