Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• ’ high aspect ratio and the hydrophobic effect, water could effectively diffuse away from the catalytic site, which enabled the enhanced formation of product. [40]. Catalysis in micelles: Micelles as nanoreactors have been extensively used in organic synthesis [31], allowing reactions in water [65] with

Interactions between photoacidic 3-hydroxynaphtho[1,2-b]quinolizinium and cucurbit[7]uril: Influence on acidity in the ground and excited state

• Jonas Becher,
• Daria V. Berdnikova,
• Darinka Dzubiel,
• Heiko Ihmels and
• Phil M. Pithan

Beilstein J. Org. Chem. 2017, 13, 203–212, doi:10.3762/bjoc.13.23

• charge providing ion–dipole interactions with the carbonyl portals of CB[7] as well as its extended π system, that was proposed to cause a higher affinity to the CB[7] due to an increased hydrophobic effect. Moreover, the naphthoquinolizinium ion resembles the quinolizinium-type alkaloids palmatine

• the binding constants of complexes between cationic ligands and cucurbiturils depend not only on the actual fit of the ligand to the host structure. In this particular case, the stabilization/destabilization of the free ligand in water, and for that matter the hydrophobic effect, may influence the

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

• functions are obtained by using data from experimentally determined structures and fitting this information to parameters. The idea here is that the binding free energy is calculated as the weighted sum of terms that are uncorrelated. These terms can be the number of hydrogen bonds, hydrophobic effect, and

Radical polymerization by a supramolecular catalyst: cyclodextrin with a RAFT reagent

• Kohei Koyanagi,
• Yoshinori Takashima,
• Takashi Nakamura,
• Hiroyasu Yamaguchi and
• Akira Harada

Beilstein J. Org. Chem. 2016, 12, 2495–2502, doi:10.3762/bjoc.12.244

• due to the hydrophobic effect. As a water-soluble radical initiator, we selected 2,2'-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044). Two hundred equivalents (equiv) of monomers, 1 equiv of α-CD-CTA, and 0.4 equiv of VA-044 were mixed in water (monomer: 1 mol/kg). After the reactants

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• interests. (a) Cyclophane receptors from Dennis Dougherty’s group in the late ‘80’s and early ‘90’s that demonstrated cation–π interactions [2]. (b) Cyclophane receptors from the Diederich group in the late ‘80’s and early ‘90’s that demonstrated the “nonclassical hydrophobic effect” [3]. (c) The Hunter

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• , and to contribute to Science’s understanding of the properties of aqueous solutions. As discussed below, the latter can be bifurcated into two general topics: the hydrophobic effect and the Hofmeister effect. However, specific molecular-level understandings of these phenomena are far from complete

• were working in organic solvents, not water. Throughout my career, water had been just under the surface of all my research endeavors: I had been working towards water-soluble cavitands and making four-helix bundles that assembled via the hydrophobic effect at UBC, I had been working with water-soluble

• zinc complexes at NYU; even non-water-soluble steroids rely in part on the hydrophobic effect to bind. The common denominator was water, “the solvent of life”. However, although we understand water quite well, we are far from fully understanding aqueous solutions [29][30], and to be frank, it’s hard to

Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex

• Chompoonut Rungnim,
• Sarunya Phunpee,
• Manaschai Kunaseth,
• Supawadee Namuangruk,
• Kanin Rungsardthong,
• Thanyada Rungrotmongkol and
• Uracha Ruktanonchai

Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251

• . [23] reviewed the hydrophobic effect of supramolecular complexes from MD simulation studies and emphasized that the non-covalent driving force of high-energy water in the cavity of cyclodextrins, cyclophanes and cucurbiturils was an essential factor for complexation with the guest molecule. MD

Cathodic hydrodimerization of nitroolefins

• Michael Weßling and
• Hans J. Schäfer

Beilstein J. Org. Chem. 2015, 11, 1163–1174, doi:10.3762/bjoc.11.131

• way reverse partially the hydrophobic effect of the alkyl groups in the tetraethylammonium cation. The dimer yield should increase with increasing radical concentration, which means that at the beginning of the reaction the dimer yield should be higher than towards the end. As olefin 1 and dimer 2 are

Why a diaminopyrrolic tripodal receptor binds mannosides in acetonitrile but not in water?

• Diogo Vila-Viçosa,
• Oscar Francesconi and
• Miguel Machuqueiro

Beilstein J. Org. Chem. 2014, 10, 1513–1523, doi:10.3762/bjoc.10.156

• and ACN (Figure 9). In ACN, a strong interaction between the sugar ring and the arms of the receptor is observed and, in water, the carbon chain lays close to the ring stabilized by the hydrophobic effect. Altogether, these results show that, in ACN, hydrogen bonds are stronger and, probably, the main

Diastereoselective synthesis of nitroso acetals from (S,E)-γ-aminated nitroalkenes via multicomponent [4 + 2]/[3 + 2] cycloadditions promoted by LiCl or LiClO₄

• Leandro Lara de Carvalho,
• Robert Alan Burrow and
• Vera Lúcia Patrocinio Pereira

Beilstein J. Org. Chem. 2013, 9, 838–845, doi:10.3762/bjoc.9.96

• hydrophobic effect can lead the reaction partners to collapse to a TS that is less hydrophobic and less destabilized than the initial state, promoting an increase in the reaction rate [17][28][29]. Aiming to improve the efficiency of the cycloaddition reactions, LiCl or LiClO4 solutions were used as a

Expanding the gelation properties of valine-based 3,5-diaminobenzoate organogelators with N-alkylurea functionalities

• Hak-Fun Chow and
• Chin-Ho Cheng

Beilstein J. Org. Chem. 2010, 6, 1015–1021, doi:10.3762/bjoc.6.114

• those of the shorter ones. Keywords: amino acids; hydrophobic effect; organogelators; self-assembly; urea; Introduction Organic gelators are an interesting group of molecules that are able to form a non-covalent three dimensional network with a particular solvent system. The ultimate result is the

RAFT polymers for protein recognition

• Alan F. Tominey,
• Julia Liese,
• Sun Wei,
• Klaus Kowski,
• Thomas Schrader and
• Arno Kraft

Beilstein J. Org. Chem. 2010, 6, No. 66, doi:10.3762/bjoc.6.66

• : electrostatic interactions; hydrophobic effect; isothermal calorimetry; protein recognition; RAFT polymers; Introduction The ability of biological receptors to bind strongly and specifically to a particular molecular target is an essential part of biological machinery. The best example is the immune system

• affinity. We therefore tentatively explain the gain in free energy by an increased classical hydrophobic effect due to the presence of additional nonpolar cyclohexyl residues throughout the polymer chain. For biological applications, it is desirable to keep the polymer size close to the size of the protein

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32