Substrate specificity of a ketosynthase domain involved in bacillaene biosynthesis

• Zhiyong Yin and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2024, 20, 734–740, doi:10.3762/bjoc.20.67

• binding of both substrate surrogates to BaeJ-KS2, but it is unclear from these experiments, if 11 is bound covalently to the protein or through non-covalent interactions. To gain further evidence for the covalent binding of 11 to BaeJ-KS2, the highly conserved Cys residue involved in substrate attachment

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

• that no new atoms are introduced into the molecule, thus ensuring first-order kinetics of the process without complexity. One of the possible mechanisms of redox-induced switching involves an intramolecular bond formation that introduces non-covalent interactions between tweezers endpoints leading to a

• electronic or geometrical properties upon oxidation or reduction. TTF and derivatives tweezers One of the most widely used electroactive moieties is tetrathiafulvalene (TTF). Its electron-donor π-system can form non-covalent interactions with various electron-poor π-systems, and those interactions can be

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

• up new possibilities for the fabrication of supramolecular structures based on the non-covalent interactions using carbon nanorings [37][38]. Despite the unique structure of the host–guest complexes, however, their electronic structures are not very attractive. This is because the complex formation

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

• remarkable advances not only highlighted the synthetic potential of photocatalysis but also served as inspiration for future developments of low-cost photocatalysis based on other non-covalent interactions. The simplicity, practicality, and broad substrate scope demonstrated by these approaches further

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• , finally, the structure with the lowest energy, with the functional PBE0-D4/mTZVPP/CPCM. The Hartree–Fock plus London dispersion (HFLD) method was used for the study of non-covalent interactions (NCI). The calculations lead to the conclusion that a reduction in electrostatic interactions and an increase in

• of non-covalent interactions within various types of supramolecular complexes [17]. One such method is HFLD [18], which can be considered a dispersion-corrected HF approach where the dispersion interaction between fragments is added at the DLPNO-CC level. The HFLD method demonstrates comparable

• performance to HF in terms of total interaction energies while maintaining the accuracy of DLPNO CCSD(T) [19]. This method proves very accurate in quantifying non-covalent interactions, such as those found in hydrogen-bonded systems, among others. Despite the relatively small cavity in the structure of

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

• Carlee A. Montgomery and
• Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

• ). The authors’ explanation for the improved reactivity of o-anisyl derivative 39 was based on its improved solubility in dichloromethane. The contact distances were both within the Van der Waals radii criteria for confirming non-covalent interactions [33], which likely contributed to the ylide’s

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• (hydroxylation, hydroperoxidation, halogenation, etc.), cross-dehydrogenative coupling and oxidative cyclization, alcohol oxidation, and the oxidation of other functional groups. Compared to other types of organocatalysis (type I and type II in Scheme 1) reversible bonding and non-covalent interactions of redox

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

• Oleg A. Levitskiy,
• Olga I. Aglamazova,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

• base platform creates an optimal balance between the covalent binding with the substrate (which does not “kill” its reactivity but precludes its redox destruction) with non-covalent interactions in the metal chiral coordination environment governing the reaction’s stereocontrol. Cyclic voltammograms

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• be performed. Supramolecular systems based on non-covalent interactions have drawn considerable attention in assembling efficient light harvesting systems (LHSs) in the last decade [60][61]. Significant attention has been centered to construct artificial LHSs via FRET (fluorescence resonance energy

Recent advances in organocatalytic asymmetric aza-Michael reactions of amines and amides

• Pratibha Sharma,
• Raakhi Gupta and
• Raj K. Bansal

Beilstein J. Org. Chem. 2021, 17, 2585–2610, doi:10.3762/bjoc.17.173

• overviews the literature published during the last 10 years concerning the asymmetric aza-MR of amines and amides catalysed by organocatalysts. Both types of the organocatalysts, i.e., those acting through non-covalent interactions and those working through covalent bond formation have been applied for the

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• molecular recognition processes have been established based on different non-covalent interactions such as hydrogen bonding [9][10][11][12], π–π interaction [13][14][15][16][17], hydrophobic effects, and amphiphilicity [18][19][20][21]. It has been highly desirable to establish concepts that could be

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

• tuning of the fluorescence behaviour and mesomorphic properties of the assemblies. Keywords: fluorescence; halogen bonding; liquid crystal; Introduction Supramolecular chemistry has proven to be an efficient approach for the development of novel smart materials, since it relies on non-covalent

• interactions, which allow for dynamic responses to external stimuli [1]. In addition, the self-assembly of the complementary molecular entities provides an easy access to functional systems and enables recyclability and self-healing properties of the materials [2]. With respect to the formation of

UV resonance Raman spectroscopy of the supramolecular ligand guanidiniocarbonyl indole (GCI) with 244 nm laser excitation

• Tim Holtum,
• Vikas Kumar,
• Daniel Sebena,
• Jens Voskuhl and
• Sebastian Schlücker

Beilstein J. Org. Chem. 2020, 16, 2911–2919, doi:10.3762/bjoc.16.240

• vibrational modes of the molecule. Especially for non-covalent interactions such as hydrogen bonding, vibrational spectroscopy has been shown to be very sensitive [10][11]. In the context of supramolecular recognition, for example, IR spectroscopy has been applied to monitor the binding of tetrapeptides by

• -covalent interactions namely hydrogen bonds, van der Waals, and/or hydrophobic interactions [1][2][3][4][5]. In this context, Schmuck and co-workers have introduced a class of synthetic receptors based on the guanidiniocarbonyl pyrrole (GCP) moiety (cf. Figure 1 top right) as a carboxylate binding site

• the results from density functional theory (DFT) calculations. Keywords: GCI; GCP; guanidiniocarbonyl indole; guanidiniocarbonyl pyrrole; UVRR; Raman spectroscopy; resonance Raman; Introduction Supramolecular ligands are capable to selectively bind to peptides and proteins via reversible non

NMR Spectroscopy of supramolecular chemistry on protein surfaces

• Peter Bayer,
• Anja Matena and
• Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

• steric accessibility is an important determining factor for calixarene binding, the overall local electrostatic potential of the protein surface as well as other non-covalent interactions such as hydrophobic interactions or aromatic ring stacking contribute to a certain selectivity for some lysine

• in the crystal structures, which enable a greater diversity of non-covalent interactions with the protein and even different binding modes on the same lysine side chain. With increasing ring size, the calixarenes promote ligand-induced ordered multimerization of proteins. Cyt c for example is

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• energetically favourable non-covalent interactions, hydrogen bonds, and van der Waals interactions formed between the DNA/RNA and solvent, and between the compound 4 and solvent. The large positive entropy changes suggest solvent release upon binding, which makes a favourable contribution to the reaction Gibbs

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

• ; Introduction The interplay of non-covalent interactions between nucleic acids and proteins or peptides is the basis of life and is also often used for the design of artificial small molecules, aiming for sensing or control of biorelevant processes. Many naturally occurring bioactive molecules contain a short

Models of necessity

• Timothy Clark and
• Martin G. Hicks

Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137

• ideas about chemical structures and reactions. This early extension of the Lewis model and the introduction of two-center three-electron bonding [44] serve as prototypes for what will become necessary improvements to handle in particular non-covalent interactions but in general any structures or

• ] or quantitative VB calculations. If we delve deeper, we find MO interpretations of, for instance, non-covalent interactions [82] coexisting with more fundamentally physical electrostatic pictures [83]. Indeed, the polarization/charge transfer shown in Figure 4 is often interpreted as donation into an

• reactions. There is, however, a need to add non-covalent interactions to the model in order to take the importance of complexation and aggregation via non-covalent interactions into account. This could be done in a purely ad hoc fashion for each type of interaction. This is how force-field developers have

Fluorohydration of alkynes via I(I)/I(III) catalysis

• Jessica Neufeld,
• Constantin G. Daniliuc and
• Ryan Gilmour

Beilstein J. Org. Chem. 2020, 16, 1627–1635, doi:10.3762/bjoc.16.135

• non-covalent interactions [8][9][10]. These collective attributes render fluorination a valuable strategy in drug discovery [11] and agrochemical development [12]. In the conception of enabling fluorination technologies, the α-fluorocarbonyl motif has emerged as a prominent target scaffold [13

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions

• in governing the endo stereocontrol. Keywords: endo-Diels–Alder stereocontrol; 2-formylpyrrole; intramolecular Heck arylation reaction; non-covalent interactions; pyrroloindoles; pyrroloisoindoles; Introduction Pyrrolizines [1][2] and pyrrolizidines [3][4], abundant in nature [4][5], are among the

Small anion-assisted electrochemical potential splitting in a new series of bistriarylamine derivatives: organic mixed valency across a urea bridge and zwitterionization

• Keishiro Tahara,
• Tetsufumi Nakakita,
• Alyona A. Starikova,
• Takashi Ikeda,
• Masaaki Abe and
• Jun-ichi Kikuchi

Beilstein J. Org. Chem. 2019, 15, 2277–2286, doi:10.3762/bjoc.15.220

• promising trigger to directly change the charge distributions of molecules and assemblies, potentially allowing tuning of the strength of non-covalent interactions, including hydrogen bonds (H-bonds) [23][24][25][26]. In this context, a number of redox-active compounds bearing H-bond donors and acceptors

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

• Jing Li,
• Qiang Shi,
• Ying Han and
• Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

• -polar solvent, acetone hampers or competes the intermolecular non-covalent interactions between the hosts and the guests, and thus resulted in a decrease of the host–guest complexation. ESIMS studies of the formation of host–guest complexes The electrospray ionization (ESI) mass spectra also confirmed

• multiple intermolecular non-covalent interactions with distances ranging from 1.651 to 2.575 Å. Compared with hosts H2 and H3, helic[6]arene H1 and its derivatives H4 and H5 all show multiple hydrogen-bonding interactions with the examined guests, which were confirmed by not only X-ray crystal structures

• ) Top view, (b) side view, and (c) packing viewed along c-axis. Blue lines denote the non-covalent interactions between H1 and G1. Solvent molecules and hydrogen atoms not involved in the non-covalent interactions were omitted for clarity. Crystal structure of complex H5·G1. (a) Top view, (b) side view

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• smaller than that in the presence of one equivalent of TBA[AuCl4] (Figure 3), although they have rather similar binding affinities. This may be due to a different extent hydrogen bonding is involved in diverse complexes and other non-covalent interactions may contribute more in the cases of (TBA)2[PtCl4

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• with their linear glycol chain counterparts, B21C7 shows great potential to be an easy-to-accessed building block to probe the non-covalent interactions and chemical transformations influenced by water molecules. Perylene diimide (PDI) and naphthalene diimide (NDI) are polycyclic aromatic chromophores

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

• preorganized structures that favor high affinity and shape-selective association of guest molecules or ions. Usually, it is the solvent that determines which non-covalent interactions are the most important for strong association. Polar interactions are often dominant in weakly polar organic solvents, and thus

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

• are working in tandem and concertedly to form networks of non-covalent interactions stabilizing the dimeric and capsular structures in the solid state. The inclusion guests affect the geometry of the cavity of the hex-NARBr and cy-NARCl, thus affecting the halogen bonding connection in the final