On the basis of a combination of new structural data (eleven single-crystal structure determinations are presented) and information from the Cambridge Structural Database, it has been shown that self-complementary hydrogen-bond based amide...amide dimers can be relied upon as effective supramolecular synthons for the assembly and organization of acac- and paddle-wheel complexes of a variety of metal(II) ions. The targeted molecular recognition event and intended extended one-dimensional motif appear with a supramolecular yield of 78% (a total of 28 structures were examined). Despite the fact that the hydrogen bonds that give rise to the R2(2)(8) motif can be disrupted by both carboxylate- and acac-ligands, as well as by solvent molecules, they remain remarkably resilient and therefore represent useful synthetic tools in inorganic crystal engineering.
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http://dx.doi.org/10.1021/ic801992t | DOI Listing |
Org Lett
March 2021
Department of Chemistry, Queen's University, Kingston, ON K7L 3N6, Canada.
Mono- and dianion species of 1,8-naphthalene diamide were generated under -BuLi/TMEDA conditions and trapped with a variety of electrophiles to give 2- and 2,7- substituted products and . Using Suzuki-Miyaura cross-coupling, mono- and di-iodinated products were converted into the corresponding 2-aryl () and 2,7-diaryl () products, respectively. The amide-amide rotation barrier of was established by VT NMR, and the structure of fluorenone structure , obtained by metalation, was secured.
View Article and Find Full Text PDFChemistry
June 2016
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
By exploiting orthogonal hydrogen bonding involving supramolecular synthons and hydrophobic/hydrophilic interactions, a new series of simple organic salt based hydrogelators derived from pyrene butyric acid and its β-alanine amide derivative, and various primary amines has been achieved. The hydrogels were characterised by microscopy, table-top rheology and dynamic rheology. FTIR, variable-temperature (1) H NMR and emission spectroscopy established the role of various supramolecular interactions such as hydrogen bonding and π-π stacking in hydrogelation.
View Article and Find Full Text PDFJ Comput Chem
March 2014
Department of Chemistry, Liaoning Normal University, Dalian, 116029, People's Republic of China.
In this article, a polarizable dipole-dipole interaction model is established to estimate the equilibrium hydrogen bond distances and the interaction energies for hydrogen-bonded complexes containing peptide amides and nucleic acid bases. We regard the chemical bonds N-H, C=O, and C-H as bond dipoles. The magnitude of the bond dipole moment varies according to its environment.
View Article and Find Full Text PDFJ Am Chem Soc
January 2009
Department of Chemistry, State University of New York, Stony Brook, New York, 11794-3400, USA.
Single-crystal-to-single-crystal (SCSC) topochemical polymerizations of diacetylenes can yield nearly defect-free conjugated polymer crystals unattainable by other methods. Aryl-substituted diacetylenes with their potentially greater conjugation have been targeted for years, but until now no one has reported a SCSC polymerization of any aryl-substituted diacetylene. This is presumably due to the rigidity of such diaryl-substituted monomers as well as the lack of control over the supramolecular structure.
View Article and Find Full Text PDFJ Am Chem Soc
January 2005
Department of Chemistry, University of Missouri-Columbia, 605 South College Avenue, Columbia, Missouri 65211, USA.
The cross-link dG-to-dG is an important product of DNA nitrosation. Its formation has commonly been attributed to nucleophilic substitution of N2 in a guaninediazonium ion by guanine, while recent studies suggest guanine addition to a cyanoamine derivative formed after dediazoniation, deprotonation, and pyrimidine ring-opening. The chemical viability of the latter mechanism is supported here by the experimental demonstration of rG-to-aG formation via rG addition to a synthetic cyanoamine derivative.
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