Synthesis of a Soluble Ureido-Naphthyridine Oligomer that Self-Associates via Eight Contiguous Hydrogen Bonds

Mayer, M.; Nakashima, Shoji; Zimmerman, Steven C.

doi:10.1021/ol050987f

Cited by 59 publications

(28 citation statements)

References 18 publications

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“…Examples of self-complementary endgroups include carboxylic acids (DA), diaminopurines (DADA), 39 ureidopyrimidones (DDAA), 15 and ureido-naphthyridine (DDAADDAA). 40 Quadruple and higher H-bonding functional groups have been shown to exhibit self-sorting with high specificity. 41 For that reason blends are considered that involve up to two different sitespecific interactions, and each associating group may only bond with associating groups of the same type, that is, cross-association of different endgroups is prohibited.…”

Section: Scopementioning

confidence: 99%

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Anthamatten¹

2007

J Polym Sci B Polym Phys

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A mean field model is developed to predict how polymer-polymer miscibility changes if polymers are functionalized with noncovalent, reversibly binding endgroups. The free-energy model is based on the Flory-Huggins mixing theory and has been modified using Painter's association model to account for equilibrium selfassociation of endgroups. Model input parameters include the length of polymer chains, a temperature-dependent interaction parameter, and a temperature-dependent equilibrium constant for each type of associating endgroup. The analysis is applied to 12 possible blend combinations involving self-complementary interactions and seven combinations involving hetero-complementary [i.e. donor-acceptor (DA)] interactions. Combinations involve both monofunctional and telechelic associating chains. Predicted phase diagrams illustrate how self-complementary interactions can stabilize two-phase regions and how DA interactions can stabilize single phase regions. The model is a useful tool in understanding the delicate balance between the combinatorial entropy of mixing polymer chains, the repulsive interactions between dissimilar polymers, and the additional enthalpic and entropic changes due to endgroup association of chain ends.

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Section: Scopementioning

confidence: 99%

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Anthamatten¹

2007

J Polym Sci B Polym Phys

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“…Formation and stability of numerous supramolecular homo-and copolymers with different self-complementary hydrogen bonding arrays have been widely studied [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. The main interest in designing self-assembling systems is to construct molecules that connect with each other in a predictable way [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies

et al. 2011

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Intermolecular interactions of 7-(RCONH)-[1H]-2-oxo-1,8-naphthyridines (R = Me, Et, i-Pr, t-Bu, 1-adamantyl (1-Ad), CF 3 , and C 2 F 5 ) containing ADAD quadruple hydrogen bonding motif were studied by liquid and solid state NMR, ESI-MS, IR, and DFT calculations. 1 H NMR was used to determine the dimerization constants of i-Pr and 1-Ad congeners in CDCl 3 . 13 C and 15 N crosspolarization (CP) magic angle spinning (MAS) NMR data suggest that compounds possess similar solid state structures. Further, mass spectral data reveal that in gas phase both Me and 1-Ad derivatives form also multimers due to lack of competitive solvent interactions. The structures of the gas phase multimers depend on the size of the alkyl group. These results are in agreement with quantum chemical calculations. Geometry optimization and 1 H NMR spectra show that in dimers that carry bulky alkyl groups (t-Bu and 1-Ad) certain hydrogen bonds are weaker than in Me, Et, and i-Pr derivatives while strong electron acceptors, CF 3 and C 2 F 5 , deshields hydrogen bonded protons but creates significant electronic F/O repulsion yielding lowering of the energy of interaction. The influence of steric effect on dimerization of quadruply hydrogen bonded dimers was correlated with the Taft E s values.

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“…In particular, Meijer's ureidopyrimidone (UPy) building block [9,10], with its characteristics of a high dimerization constant and synthetic accessibility, has found widespread applications in supramolecular chemistry, materials science, and catalysis [11,12]. Zimmerman's ureidodeazapterin and ureidonaphthyridine modules are also successful examples of heterocyclic building blocks [13][14][15][16].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C₁₃H₁₂N₄O₂

Pansuriya

Patel

Friedrich

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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C 13 H 12 N4O 2 , orthorhombic, Pbca (no. 61), a = 16.2353(11) Å, b = 16.8474(12) Å, c = 36.028(2) Å, V = 9854.5(11) Å 3 , Z = 32, CCDC no.: 1457416In the gure only one out of four crystallographically independent molecules is shown. Tables 1-3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialIsoniazid (1 g, 7.2 mmol) and phenyl isocyanate (1 g, 8.3 mmol) were mixed in methanol (30 mL) thoroughly and re uxed for 30 min. After the reaction was completed, the resulting mixture was cooled to room temperature. The products were collected by ltration (1.4 g, 80% yield); M.p.:422-424 K. The title compound was recrystallized from a mixture of methanol and dichloromethane (50:50), colourless single crystals were obtained by slow evaporation. Experimental detailsAbsorption correction was performed using SADABS (Bruker, 2006). All hydrogen atoms were placed in idealised positions

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Synthesis of a Soluble Ureido-Naphthyridine Oligomer that Self-Associates via Eight Contiguous Hydrogen Bonds

Cited by 59 publications

References 18 publications

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies

Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C₁₃H₁₂N₄O₂

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Synthesis of a Soluble Ureido-Naphthyridine Oligomer that Self-Associates via Eight Contiguous Hydrogen Bonds

Cited by 59 publications

References 18 publications

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Phase behavior predictions for polymer blends containing reversibly associating endgroups

Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies

Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C13H12N4O2

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Crystal structure of N-phenyl-2-(pyridin-4-ylcarbonyl)hydrazinecarboxamide with Z′ = 4, C₁₃H₁₂N₄O₂