Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• interesting alternative to hydrogen bonding, which constitute an indispensable type of non-covalent interaction utilized in several catalytic approaches [81][82][83][84][85][86][87][88]. In 2008, Bolm introduced the use of perfluoroiodoalkanes as XB catalysts and the field gained widespread attention as an

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• . An EDA complex was formed through non-covalent interaction between the redox ester 10 and n-Bu4NI (Scheme 7). Subsequently, upon the photoexcitation, radical pairs I were generated via a SET process, accompanied by the liberation of CO2 and the phthalimide anion. The recombination of the alkyl

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• the complex. Every ΔTm value here reported was the average of at least two measurements. The error in ΔTm is ±0.5 °C. Isothermal titration calorimetry (ITC) experiments: A non-covalent interaction study of Phen-Py-1 with the human enzyme mutant DPP III E451A was performed on a MicroCal PEAQ-ITC

Tuning the solid-state emission of liquid crystalline nitro-cyanostilbene by halogen bonding

• Subrata Nath,
• Alexander Kappelt,
• Matthias Spengler,
• Bibhisan Roy,
• Jens Voskuhl and
• Michael Giese

Beilstein J. Org. Chem. 2021, 17, 124–131, doi:10.3762/bjoc.17.13

• behaviour of halogen-bonded liquid crystals has been reported. In 2014, Tothadi and Desiraju reported on a new supramolecular synthon based on the non-covalent interaction between 1,4-dinitrobenzene and iodobenzene [13]. Their structural analysis of a series of ternary cocrystals revealed that the nitro

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

• Annike Weißenstein,
• Myroslav O. Vysotsky,
• Ivo Piantanida and
• Frank Würthner

Beilstein J. Org. Chem. 2020, 16, 2032–2045, doi:10.3762/bjoc.16.170

• several decades, consequently becoming increasingly complex [5][6][7]. This includes examples incorporating several types of non-covalent interaction with DNA/RNA (intercalation, groove binding, positive–negative charge interaction [5][8]) in one molecule or even modified biomacromolecules (e.g., proteins

• examined first by means of the thermal denaturation method. Various double-stranded DNA or RNA are known upon heating to dissociate into two single-stranded polynucleotides at a characteristic well-defined temperature (Tm value). A non-covalent interaction of small molecules usually increases the thermal

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• dimers, respectively, while the former shows boat conformation and the latter forms rectangle conformation. Triazolium salts form a linear polymer with polyiodide. Keywords: aggregation; 4,5-diiodo-1,2,3-triazolium salts; halogen bond; non-covalent interaction; Introduction The halogen bond (XB) is a

Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

• Fangfang Pan,
• Mohadeseh Dashti,
• Michael R. Reynolds,
• Kari Rissanen,
• John F. Trant and
• Ngong Kodiah Beyeh

Beilstein J. Org. Chem. 2019, 15, 947–954, doi:10.3762/bjoc.15.91

• type of directional non-covalent interaction, is regarded as the “long lost brother” of hydrogen bonding (HB) [6][7]. Although XB in many aspects is very similar to HB, and in most cases not as strong as classical HB, the character of XB, such as hydrophobicity, adjustability, or softness, allows these

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

• bonding (case 3) is also the reason for using the term “non-covalent interaction”, another frequently used term is “weak intermolecular interaction”. Both terms have disadvantages. Weak intermolecular interaction does not cover those cases in which intramolecular interactions cause stabilization, e.g

• ., when a large n-alkane changes from the linear to the hairpin structure; non-covalent interaction, on the other hand, does not exclude creation and stabilization of cation–anion pairs or zwitterions and their stabilization by Coulomb interaction. Weak molecular interaction is certainly the best term for

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• guanine bases) to DNA is irreversible and causes permanent stall of transcription leading to cell death. Non-covalent interaction between small molecules and DNA is usually reversible and can further be classified as minor groove binders, intercalators, backbone binders, and major groove binders. There

Stereodynamic tetrahydrobiisoindole “NU-BIPHEP(O)”s: functionalization, rotational barriers and non-covalent interactions

• Golo Storch,
• Sebastian Pallmann,
• Frank Rominger and
• Oliver Trapp

Beilstein J. Org. Chem. 2016, 12, 1453–1458, doi:10.3762/bjoc.12.141

• ) barriers. Functionalization of stereodynamic BIPHEP ligands at the biaryl core offers multiple possibilities. The introduction of achiral, non-covalent interaction sites allows for ee determination of chiral analytes via NMR spectroscopy [21] as well as deracemization of the BIPHEPs with HPLC stationary

• achiral auxiliaries or binding sites. In this study, we chose amide bond formation with 3,5-dichlorobenzoyl chloride (Figure 2B) in connection with our recent report [21] on non-covalent interaction properties of stereodynamic BIPHEP ligands with this binding site that is well known in HPLC stationary

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• between thiophenes C and G is higher (18.36°) but the two S-atoms are involved in a weak non-covalent interaction with a distance of 3.81 Å between them. The strong π–π stacking interaction and the presence of multiple S–S non-covalent interactions in the H-shaped TTF-oligothiophene system 54 (n = 2) made

Substitution effect and effect of axle’s flexibility at (pseudo-)rotaxanes

• Friedrich Malberg,
• Jan Gerit Brandenburg,
• Werner Reckien,
• Oldamur Hollóczki,
• Stefan Grimme and
• Barbara Kirchner

Beilstein J. Org. Chem. 2014, 10, 1299–1307, doi:10.3762/bjoc.10.131

• to many benchmark calculations (see, e.g., [49][51][56]), both functionals perform very similar for non-covalent interaction (TPSS-D3 being even somewhat better for hydrogen bonding), which supports the above conclusion. Substitution effect The interaction energies in Table 2 show that the more

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89

• planar. Keywords: discotic liquid crystals; shape-persistent macrocycles; templates; X-ray scattering; Introduction The supramolecular chemistry of shape-persistent macrocycles has enormously expanded during the past several years [1][2][3][4][5][6]. It covers the non-covalent interaction between the

Conformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect

• Josué M. Silla,
• Claudimar J. Duarte,
• Rodrigo A. Cormanich,
• Roberto Rittner and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2014, 10, 877–882, doi:10.3762/bjoc.10.84

• bond. Likewise, the 'quantum' nature of this hydrogen bond (the nF→σ*NH interaction) is not detected by NBO analysis. However, the new non-covalent interaction (NCI) approach, which is based on the electron density and its derivatives, enables the identification of non-covalent interactions by means of

• ]. Quantum theory of atoms in molecules (QTAIM) calculations were performed to search for possible hydrogen bonds and their stabilities using the AIMAll program [27]. The non-covalent interaction (NCI) method was carried out by using the NCIPLOT program [28]. NCI domains and the plot of reduced density

Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15

• Hynek Balcar,
• Tushar Shinde,
• Naděžda Žilková and
• Zdeněk Bastl

Beilstein J. Org. Chem. 2011, 7, 22–28, doi:10.3762/bjoc.7.4

• in accord with the amount of Ru removed from the support by leaching as determined from elemental analysis. The results obtained suggest that the Ru species in 3/SBA-15 were attached to the sieves by a non-covalent interaction (probably via physical adsorption). The small residual Ru content, which

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

• Kari Raatikainen,
• Massimo Cametti and
• Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

• engineering; halogen bonding; hydrogen bonding; supramolecular chemistry; weak interactions; Introduction Non-covalent interaction, such as hydrogen bonding and metal coordination represent the basic set of tools for the construction of elaborate architectures in the supramolecular chemistry of organic or

• chemistry [2]. Halogen bonding (XB) is the non-covalent interaction involving halogen atoms as electrophilic species [3]. The first reports of these interactions, only later classified as halogen bonds, date back to the late 1960’s [4]. In the following years, several X-ray studies demonstrated the