Spatial arrangements of cyclodextrin host–guest complexes in solution studied by ¹³C NMR and molecular modelling

• Konstantin Lebedinskiy,
• Ivan Barvík,
• Zdeněk Tošner,
• Ivana Císařová,
• Jindřich Jindřich and
• Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

• to compare the solid-state structure of the guest 2–α-CD host complex with its proposed solution state conformations (Figure 6). Conclusion We have demonstrated that simple 13C NMR analyses of properly chosen Cs symmetric compounds varying in size can be used to estimate the host–guest spatial

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

• 30: Experimental procedures, plot of the solid-state structure of 2f, crystallographic data, NMR spectra, UV–vis spectra and experimental and simulated time conversion plots for the zwitterion formation. Funding Funding by the Christian Doppler Research Association (Austrian Federal Ministry for

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• lower 25% and 26% yields. Lastly, we synthesized 3f using the standard procedure for iodoliums with more sophisticated benzimidazole-containing diaryliodonium salt, but we only observed a reproducible yield of 8%. The analysis of its solid-state structure showed the desired connectivity [36]. Conclusion

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• , emphasising the structural motif's ability to stabilise guest molecules through primary and secondary sphere bonding interactions. Compound 19-Cr, similarly to 18a-Ti and 18a-V, also exhibited paramagnetic features. The solid state structure demonstrated the complex featuring a Cr3+ cation bound in a

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• 0.65 kcal·mol−1 over the (pm) alternated conformation, suggesting that these two conformations could coexist in solution. Furthermore, the (pm) dimeric model adopt a structure analogous to the solid-state structure of an N-hydroxypeptoid dimer, with very similar dihedral angles and φ angles opposite to

Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes

• Henrik Hupatz,
• Marius Gaedke,
• Hendrik V. Schröder,
• Julia Beerhues,
• Arto Valkonen,
• Fabian Klautzsch,
• Sebastian Müller,
• Felix Witte,
• Kari Rissanen,
• Biprajit Sarkar and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209

• intramolecular folding which was observed in the solid-state structure and is likely also present in solution, as indicated by a charge-transfer band. Nevertheless, it might be applicable for redox-controlled metal-sensing [60][61][62]. On the contrary, NDIC8 forms pseudo[2]rotaxanes and facilitates the

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• structure of rotaxane 1a was determined by single crystal X-ray diffraction of crystals obtained by slow evaporation of a dichloromethane solution. The analysis of the X-ray solid-state structure of the rotaxane 1a showed a significant difference to Leigh’s rotaxane I [4]. Rotaxane I only presented two

• was E1/2 = +0.380 V vs SCE showing that rotaxane 1a retained the redox properties of the parent ferrocene [21][22]. Importantly, the full reversibility of the one electron oxidation–reduction process attested to the stability of the electroactive system. Solid-state X-ray structure The solid-state

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• -phenyl ring in C-H···N [36][37][38][39] and C-H···π [40][41][42][43][44][45][46][47][48][49] interactions (Figure 2, for details, see Supporting Information File 1). It is noteworthy to mention that there are no significant π···π interactions in the solid-state structure of 5a (for details, see

1,5-Phosphonium betaines from N-triflylpropiolamides, triphenylphosphane, and active methylene compounds

• Vito A. Fiore,
• Chiara Freisler and
• Gerhard Maas

Beilstein J. Org. Chem. 2019, 15, 2603–2611, doi:10.3762/bjoc.15.253

• triflamide anion departs, remain to be answered. Phosphonium betaines 3 prepared. An E:Z ratio of 100:0 means that only the E-isomer was observed in the NMR spectra. Solid-state structure of E-3a (ORTEP plot), two symmetry-independent molecules in the triclinic unit cell. Solid-state structure of E-3b·CH2Cl2

• (ORTEP plot); CH2Cl2 solvate molecule not shown. Solid-state structure of E-3e·H2O·CH2Cl2 (ORTEP plot). The CH2Cl2 solvate molecule is disordered. Hydrogen-bonded H2O molecule: O1···O2 2.907(2) Å, angle O1···H–O2 169(3)°. Solid-state structure of Z-3e (ORTEP plot). Stable betaines I–IV. Reactions of N

Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls

• Dong-Hao Li and
• Bradley D. Smith

Beilstein J. Org. Chem. 2019, 15, 1086–1095, doi:10.3762/bjoc.15.105

• -Bu). a) Chemical structure of β-D-glucopyranose and the solid-state structure of its complexes with macrocycle B (X = CH). b) Schematic view of tetralactam B encapsulating glucose (R = O) or glucosammonium (R = NH2+) with stabilizing secondary interactions provided by back-folding of a peripherally

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

• Pedro N. Batalha,
• Luana da S. M. Forezi,
• Maria Clara R. Freitas,
• Nathalia M. de C. Tolentino,
• Ednilsom Orestes,
• José Walkimar de M. Carneiro,
• Fernanda da C. S. Boechat and
• Maria Cecília B. V. de Souza

Beilstein J. Org. Chem. 2019, 15, 388–400, doi:10.3762/bjoc.15.35

• structure as shown in Figure 6. As can be seen in Figure 6, attached to the central oxoquinoline ring is an ethyl substituent bonded to N1 and the carboxamide group is attached to C3. The solid-state structure confirms the regioselectivity of the reaction. It is important to note from the crystalline

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

• Hiroshi Morikawa,
• Jun-ichi Yamaguchi,
• Shun-ichi Sugimura,
• Masato Minamoto,
• Yuuta Gorou,
• Hisatoyo Morinaga and
• Suguru Motokucho

Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13

• reported in our previous study [27]. Of these, 1a has already been synthesised by other groups [10][11] as well as our group. Particularly, Kleij et al. revealed the solid-state structure of 1a via X-ray analysis [11], but the isolation and characterisation of 1d has only been reported by our group. Herein

• coupling constants match well the conformations in Figure 5 although the signal c for 1d unfortunately overlaps with other signals. The structure of 1a is in good agreement with the solid-state structure reported previously [11]. Conformations of the four LMdiols were also considered in the same manner as

The activity of indenylidene derivatives in olefin metathesis catalysts

• Maria Voccia,
• Steven P. Nolan,
• Luigi Cavallo and
• Albert Poater

Beilstein J. Org. Chem. 2018, 14, 2956–2963, doi:10.3762/bjoc.14.275

• generate and/or describe the activity in olefin metathesis of the new indenylidene derivatives. The phenyl substituent of the indenylidene is perpendicular to the indenyl moiety in the solid-state structure [34], as Nolan and co-workers first described in 1999 [35]. For complexes 3–6, where the phenyl ring

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

• Matthew J. Styles and
• Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

• ) [21][22]. C) The solid-state structure of the SdiA homodimer (PDB 4Y15; monomers shown in green and grey) bound to OOHL (cyan) [22]. D) Selected residues surrounding OOHL (cyan) in the SdiA ligand binding pocket (from PDB 4Y15 [22]): hydrogen bond acceptors/donors (orange), hydrophobic residues (grey

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• decrease. Next, a X-ray analysis was performed from the dU macrocycle 8, which was crystallized from methanolic solution containing traces of water. Colorless needles with a melting point of 260–265 °C (decomp.) were obtained. The solid state structure of the macrocycle is displayed in Figure 2. The X- ray

A hemicryptophane with a triple-stranded helical structure

• Augustin Long,
• Olivier Perraud,
• Erwann Jeanneau,
• Christophe Aronica,
• Jean-Pierre Dutasta and
• Alexandre Martinez

Beilstein J. Org. Chem. 2018, 14, 1885–1889, doi:10.3762/bjoc.14.162

• 1 than for 6 with Δδ = 0.38 ppm for the CH2NH and of Δδ = 0.19 ppm for the Ar–O–CH2–Ar of 1, compared to 0.07 ppm and 0.05 ppm for 6, respectively (Figure 3). This is consistent with a more rigid structure of cage 1 in solution, as suggested by the solid-state structure. Conclusion In summary, we

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

• Akira Yoshimura,
• Michael T. Shea,
• Cody L. Makitalo,
• Melissa E. Jarvi,
• Gregory T. Rohde,
• Akio Saito,
• Mekhman S. Yusubov and
• Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

• refrigerator for several weeks. Solutions of 7a in CDCl3 or CD3CN did not show any decomposition even after storage for over one month at room temperature. The solid state structure of compound 7a was characterized by X-ray crystallography. A single crystal X-ray diffraction of 7a confirmed the bicyclic

Polysubstituted ferrocenes as tunable redox mediators

• Sven D. Waniek,
• Jan Klett,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2018, 14, 1004–1015, doi:10.3762/bjoc.14.86

• the occurrence of distinguishable C=O bands [54][76][77]. For example, two different molecules of monoester 1 are present in the asymmetric unit of the solid-state structure [76], leading to different C=O stretching vibration bands (Figure 3a). In contrast to the solid-state IR spectra, only a single

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• 3 by a solid-state structure (Figure 1). Details of the structure determination are given in Supporting Information File 1, Table S1. The absorption spectra (Figure 2) were measured in dichloromethane solution at ambient temperature. The complexes show almost identical absorption behavior with only

• ). Supporting Information The Supporting Information contains NMR-spectra, additional figures, details of the solid state structure determination and computational details. CCDC 1823322 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http

• ://www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: +44 1223 336033. Supporting Information File 67: NMR spectra, additional figures, details of the solid state structure determination

The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones

• Ommid Anamimoghadam,
• Saira Mumtaz,
• Anke Nietsch,
• Gaetano Saya,
• Cherie A. Motti,
• Jun Wang,
• Peter C. Junk,
• Ashfaq Mahmood Qureshi and
• Michael Oelgemöller

Beilstein J. Org. Chem. 2017, 13, 2833–2841, doi:10.3762/bjoc.13.275

• -isomers was again observed (Table 4, entries 26 and 27). The solid state structure of the amination product (Z)-8a was furthermore established by X-ray crystal structure analysis (Figure 4). The phenyl group of the arylmethylene unit is positioned almost perpendicular to the isoindolinone ring on top of

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• NOEs within the 2/β-CD complex points out that the overall geometry is very much similar to that described for 1/β-CD. The approximate and qualitative picture derived from NOE restraints is in good agreement with the solid state structure of the two complexes obtained from single crystal X-ray

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• ) 176(2)°; N4–H···Cl, N4···Cl 3.320(2) Å, NH···Cl 2.53(2) Å, <(N4–H···Cl) 148(2)°. Left: solid-state structure of 9b·H2O (ORTEP plot). Right: centrosymmetric hydrogen-bonded dimer of (CF3SO3)−·H2O (Mercury plot); the substituents at the triazole ring are not complete. Selected bond lengths (Å): C1–N1

• ···O8 (1−x, 1−y, 1−z), O11–Ha 0.95 Å, O11···O8 2.979(3) Å, Ha···O8 2.05 Å, <(O11–Ha···O8) 169°. Solid-state structure of mesoionic compound 7a (ORTEP plot); thermal displacement ellipsoids are drawn at the 30% probability level. Selected bond lengths (Å): C1–N1 1.343(1), C1–N3 1.398(1), C1–N5 1.322(1

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• the spacer length, the solvent-filled pore systems in the solid-state structures have been tuned and structural features such as porosity of the materials have been investigated by PXRD, TGA analysis and sorption studies. Results and Discussion Recently, we reported on the synthesis and solid-state

• structure of dodecaacid C2 (Cn stands for Th symmetrical hexakisadducts C60{C[COO(CH2)n−1COOH]2}6, see Figure 1) revealing a complex hydrogen-bonding network in the crystalline state [57]. Based on this initial finding, we also utilized C2 and elongated derivative C3 as organic connectivity centers in metal

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• ). Molecular structure of compound 3a (ORTEP plot with 50% probability level). Molecular structure of compound 4b (ORTEP plot with 50% probability level). Superimposition fit of the two conformers, which exist in the ratio of 1:1 in the solid state structure of compound 4b (label A marks the atoms of the

A T-shape diphosphinoborane palladium(0) complex

• Patrick Steinhoff and
• Michael E. Tauchert

Beilstein J. Org. Chem. 2016, 12, 1573–1576, doi:10.3762/bjoc.12.152

• solid-state structure of 9 displayed a slightly distorted T-shape geometry around the palladium center. A short Pd1–B1 distance of 2.243(2) Å (cf. complex 2: 2.194(3) Å) and a significant pyramidalization at the boron center (ΣBα = 341°) is observed, indicating a strong Pd(0)→B bond. The distance