Tailor-made naphthyridines: Self-assembling multiple hydrogen-bonded supramolecular architectures from dimer to helix

Goswami, Shyamaprosad; Dey, Swapan; Gallagher, John F.; Lough, Alan J.; García-Granda, Santiago; Torre-Fernández, Laura; Alkorta, Ibón; Elguero, José

doi:10.1016/j.molstruc.2007.01.024

Cited by 29 publications

(18 citation statements)

References 45 publications

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“…In addition, in the cis monomers, the two HB donors are located in the same side of the molecule as well the HB acceptor in the opposite. This disposition favors the secondary attractive interactions [32,33]. Finally, all these results are in line with the Gustafsson paradox [33][34][35][36] that proposed that the least stable configuration is the one with the larger acidity and basicity.…”

Section: Table IIIsupporting

confidence: 87%

Glyoxal oligomers: A computational study

Solimannejad

Massahi

Alkorta

2011

Int J of Quantum Chemistry

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Ab initio calculations at MP2/6-311þþG(2d,2p) computational level was used to analyze interactions between glyoxal (OCHCHO) dimers and trimers in the gas phase. The structures obtained have been analyzed with the atoms in molecules and natural bond orbital methodologies. Eight minima were located on the potential energy surface of the dimers. Eighteen different structures have been obtained for the trimers. CHÁÁÁO type of interactions is clustering OCHCHO molecules in studied oligomers. Stabilization energies of dimers and trimers including basis set superposition error and ZPE corrections are in the range 4-8 kJ mol À1 and 12-19 kJ mol À1 , respectively. Blue shift of CH bond upon complex formation in the ranges between 30-45 and 30-55 cm À1 was predicted for dimers and trimers, respectively.

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Section: Table IIIsupporting

confidence: 87%

Glyoxal oligomers: A computational study

Solimannejad

Massahi

Alkorta

2011

Int J of Quantum Chemistry

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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%

“…The number and order of HB-donors (D) and HB-acceptors (A) influence the relative stability of complexes due to the changes in SIs order and type [32,33]. Thus, taking into account SIs in the quadruple hydrogen bonded complexes, ADDA/DAAD-type complex is more stable than ADAD/ DADA-pair [19,22,42]. It is known that 2,7-disubstituted-1,8-naphthyridines form quadruple hydrogen bonded complexes [9,15,36,[43][44][45], which in the case of 7-acylamino-[1H]-2-oxo-1,8-naphthyridine are stabilized by an ADAD/DADA motif [19].…”

Section: Introductionmentioning

confidence: 99%

“…Thus, taking into account SIs in the quadruple hydrogen bonded complexes, ADDA/DAAD-type complex is more stable than ADAD/ DADA-pair [19,22,42]. It is known that 2,7-disubstituted-1,8-naphthyridines form quadruple hydrogen bonded complexes [9,15,36,[43][44][45], which in the case of 7-acylamino-[1H]-2-oxo-1,8-naphthyridine are stabilized by an ADAD/DADA motif [19]. It is also worth to mention that even weak CHÁÁÁN/O hydrogen bonding contacts may stabilize the infinite tapes of 2,7-disubstituted-1,8-naphthyridines in crystal [45].…”

Section: Introductionmentioning

confidence: 99%

“…It is also worth to mention that even weak CHÁÁÁN/O hydrogen bonding contacts may stabilize the infinite tapes of 2,7-disubstituted-1,8-naphthyridines in crystal [45]. The aim of this work is to perform a systematic study on the steric and electronic effects affecting the intermolecular interactions in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines (Scheme 1) because very scarce data on the topic has been published so far [19,39].…”

Section: Introductionmentioning

confidence: 99%

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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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The Two Faces of Hydrogen‐Bond Strength on Triple AAA–DDD Arrays

Lopéz¹,

Caramori²,

Coimbra³

et al. 2013

ChemPhysChem

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Systems that are connected through multiple hydrogen bonds are the cornerstone of molecular recognition processes in biology, and they are increasingly being employed in supramolecular chemistry, specifically in molecular self-assembly processes. For this reason, the effects of different substituents (NO2, CN, F, Cl, Br, OCH3 and NH2) on the electronic structure, and consequently on the magnitude of hydrogen bonds in triple AAA-DDD arrays (A=acceptor, D=donor) were evaluated in the light of topological [electron localization function (ELF) and quantum theory of atoms in molecules (QTAIM)], energetic [Su-Li energy-decomposition analysis (EDA) and natural bond orbital analysis (NBO)], and geometrical analysis. The results based on local H-bond descriptors (geometries, QTAIM, ELF, and NBO) indicate that substitutions with electron-withdrawing groups on the AAA module tend to strengthen, whereas electron-donating substituents tend to weaken the covalent character of the AAA-DDD intermolecular H-bonds, and also indicate that the magnitude of the effect is dependent on the position of substitution. In contrast, Su-Li EDA results show an opposite behavior when compared to local H-bond descriptors, indicating that electron-donating substituents tend to increase the magnitude of H-bonds in AAA-DDD arrays, and thus suggesting that the use of local H-bond descriptors describes the nature of H bonds only partially, not providing enough insight about the strength of such H bonds.

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Tailor-made naphthyridines: Self-assembling multiple hydrogen-bonded supramolecular architectures from dimer to helix

Cited by 29 publications

References 45 publications

Glyoxal oligomers: A computational study

Glyoxal oligomers: A computational study

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

The Two Faces of Hydrogen‐Bond Strength on Triple AAA–DDD Arrays

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