Extremely Strong and Readily Accessible AAA−DDD Triple Hydrogen Bond Complexes

Djurdjevic, Smilja; Leigh, David A.; McNab, Hamish; Parsons, Simon; Teobaldi, Gilberto; Zerbetto, Francesco

doi:10.1021/ja067410t

Cited by 102 publications

(63 citation statements)

References 14 publications

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“…The calculated binding energies and free energies are listed in Table 4. The [43]. It was emphasized earlier by Zimmerman that the secondary electrostatic interaction proposal is not general such as a DAAD-ADDA complex was found to be more strongly bound than a DDAA-AADD pair even though the former has two repulsive interactions while the later has two attractive interactions [31].…”

Section: Triply H-bonded Complexesmentioning

confidence: 99%

“…In addition, we also thoroughly investigated two newly developed triply H-bonded complexes. One is a well-designed conformer-independent triply H-bonded complex [42], the other was reported to be the most strongly bound neutral H-bonded complex with a DDD-AAA array [43]. In our research, we aim to seek an automated, robust and reliable computational tool to study H-bonding and van der Waals interactions, respectively, for practical chemists and undergraduate students, which can help them to make scientific discoveries and predictions before "setting foot in the laboratory" [31].…”

mentioning

confidence: 99%

“…In our research, we aim to seek an automated, robust and reliable computational tool to study H-bonding and van der Waals interactions, respectively, for practical chemists and undergraduate students, which can help them to make scientific discoveries and predictions before "setting foot in the laboratory" [31]. Indeed, our calculations provide critical and useful insights for the latest experimental measurements and popular explanations on the stabilities of the H-bonded complex of the DDD-AAA array in solution [43].…”

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confidence: 99%

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Computational study of the thermodynamic stabilities of hydrogen-bonded complexes in solution

2014

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Section: Triply H-bonded Complexesmentioning

confidence: 99%

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Computational study of the thermodynamic stabilities of hydrogen-bonded complexes in solution

2014

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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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“…The same is true for AAA/DDD [14][15][16][17] versus DDA/AAD [18,19] versus ADA/DAD pairs [7,8,[20][21][22]. Although the ADA and the DAD motifs are not self-complementary, their selfassociation is still possible due to rotamerism (Scheme 1) or tautomerism [23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

et al. 2010

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Association constants of 2,6-bis(alkylcarbonylamino)pyridines (alkyl = methyl or ethyl) and their perfluoroalkyl analogues with succin-and maleimide as well as with 2,2 0 -dipyridylamine (complementary DAD and ADA hydrogen bonding motifs are responsible for formation of the associates) have been determined by NMR titrations and quantum chemical calculations. Interactions of 2,6-bis (alkylcarbonylamino)pyridines with imides differ by character from these of perfluoroalkyl analogues. Such large difference was not observed for the 2,2 0 -dipyridylamine associates. Since fluorine atoms cause carbonylamino groups to be stronger hydrogen bond donors, perfluorinated species of this type were found to be more stable. Single crystal X-ray structures of 2,6-bis(trifluoromethylcarbonylamino)pyridine and 2,6-bis(pentafluoroethylcarbonylamino)pyridine have been also determined.

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Extremely Strong and Readily Accessible AAA−DDD Triple Hydrogen Bond Complexes

Cited by 102 publications

References 14 publications

Computational study of the thermodynamic stabilities of hydrogen-bonded complexes in solution

Computational study of the thermodynamic stabilities of hydrogen-bonded complexes in solution

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

NMR and quantum chemical studies on association of 2,6-bis(acylamino)pyridines with selected imides and 2,2′-dipyridylamine

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