The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

Ośmiałowski, Borys; Kolehmainen, Erkki; Valkonen, Arto; Kowalska, Magdalena; Ikonen, Satu

doi:10.1007/s11224-013-0283-4

Cited by 11 publications

(5 citation statements)

References 68 publications

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“…By replacing water/methanol with chloroform, we observed a significant enhancement in the RDF peak at r ∼0.25 nm (Figure d), which was attributed to the bifurcated hydrogen bonds (C–H···O bond, 0.19–0.25 nm) formed between the ether oxygens and chloroform, as reported previously. , This indicated a strong interaction between chloroform and PE5, which was supported by the highest solvent accessible area observed for PE5 in chloroform. We note that dispersion attractions or steric repulsions might also contribute to the distant interactions between chloroform and PE5, due to the large size of a chloroform molecule (Figure d).…”

Section: Results and Discussionsupporting

confidence: 84%

Compact Peptoid Molecular Brushes for Nanoparticle Stabilization

et al. 2022

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Controlling the interfaces and interactions of colloidal nanoparticles (NPs) via tethered molecular moieties is crucial for NP applications in engineered nanomaterials, optics, catalysis, and nanomedicine. Despite a broad range of molecular types explored, there is a need for a flexible approach to rationally vary the chemistry and structure of these interfacial molecules for controlling NP stability in diverse environments, while maintaining a small size of the NP molecular shell. Here, we demonstrate that low-molecular-weight, bifunctional comb-shaped, and sequence-defined peptoids can effectively stabilize gold NPs (AuNPs). The generality of this robust functionalization strategy was also demonstrated by coating of silver, platinum, and iron oxide NPs with designed peptoids. Each peptoid (PE) is designed with varied arrangements of a multivalent AuNP-binding domain and a solvation domain consisting of oligo-ethylene glycol (EG) branches. Among designs, a peptoid (PE5) with a diblock structure is demonstrated to provide a superior nanocolloidal stability in diverse aqueous solutions while forming a compact shell (∼1.5 nm) on the AuNP surface. We demonstrate by experiments and molecular dynamics simulations that PE5-coated AuNPs (PE5/AuNPs) are stable in select organic solvents owing to the strong PE5 (amine)–Au binding and solubility of the oligo-EG motifs. At the vapor–aqueous interface, we show that PE5/AuNPs remain stable and can self-assemble into ordered 2D lattices. The NP films exhibit strong near-field plasmonic coupling when transferred to solid substrates.

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Section: Results and Discussionsupporting

confidence: 84%

Compact Peptoid Molecular Brushes for Nanoparticle Stabilization

et al. 2022

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“…Weak hydrogen bonds involving carbon-bonded hydrogen atoms have been observed and described in other structures, and their features match those reported in Table S8 (Ośmiałowski et al, 2013).…”

Section: The Conformations Of Niflumic Acid and The Effect On The Pha...supporting

confidence: 82%

The solid state of anti-inflammatory morniflumate diniflumate: A cocrystalline salt

Céolin

Robert

Allouchi

et al. 2021

International Journal of Pharmaceutics

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“…Interestingly enough, the sum of these N–H···O and C–H···O binding energies is roughly equivalent to our calculated per-molecule binding energy of the isatin pentamer. Unlike some computational approaches, , DFT does not produce a breakdown of the percent contribution of the N–H···O and C–H···O hydrogen bond contribution; however, we believe that the presence of the C–H···O hydrogen in the isatin pentamer structure is a critical contributing factor to the exceptional stability of the isatin pentamer. This exceptional stability of the isatin pentamer is consistent with the observation that only isatin has higher- n oligomers in its mass spectrum, and 3M2O and 7-fluoroisatin do not.…”

Section: Results and Discussionmentioning

confidence: 77%

C–H···O Hydrogen Bonding in Pentamers of Isatin

et al. 2017

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Self-assembled monolayers of 1H-indole-2,3-dione (isatin), 3-methyl 2-oxindole, and 7-fluoroisatin are observed on the Au(111) surface via scanning tunneling microscopy (STM). We observed that isatin forms pentamers with density functional theory providing support for a cyclic structure stabilized by both N−His made between the 7-position C−H acting as the hydrogen bond donor and the 3-position carbonyl as the hydrogen bond acceptor, and calculations show that the isatin pentamer structure is 12 kJ/mol more stable than the dimer. When the 3-position carbonyl is removed and replaced with a methyl group (3-methyl 2-oxindole), we observe a monolayer with a mixture of catemer chains and pentameric clusters that are qualitatively different from those of isatin. Pentamer formation is completely broken when the 7position hydrogen is removed and replaced with fluorine; the monolayer of 7-fluoroisatin is composed of a mixture of close packed ordered domains and hexamer clusters. The role of C−H•••O bonding in forming isatin pentamers is supported by electrospray ionization mass spectrometry measurements, which show a propensity for isatin cluster formation, including magic-number isatin pentamers, while 3-methyl 2-oxindole and 7-fluoroisatin show relatively little clustering under the same conditions.

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The influence of CH bond polarization on the self-association of 2-acylaminopyrimidines by NH/CH···O/N interactions: XRD, NMR, DFT, and AIM study

Cited by 11 publications

References 68 publications

Compact Peptoid Molecular Brushes for Nanoparticle Stabilization

Compact Peptoid Molecular Brushes for Nanoparticle Stabilization

The solid state of anti-inflammatory morniflumate diniflumate: A cocrystalline salt

C–H···O Hydrogen Bonding in Pentamers of Isatin

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