Proton sponges

Llamas-Saíz, Antonio L.; Foces‐Foces, C.; Elguero, José

doi:10.1016/0022-2860(94)08367-3

Cited by 221 publications

(175 citation statements)

References 68 publications

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“…The average value for intramolecular N--H bond lengths of hydrogen bonds in 63 organic crystals has been found to be 1.02 (12) ,& (Llamas-Saiz et al, 1994). Structural studies at low temperature on this protonated proton sponge, performed for various salts (Kanters, Schouten, Duisenberg et al, 1991;Kanters, Schouten, Kroon & Grech, 1991;Kanters, Horst et al, 1992;Mallinson et al, 1997;Miller et al, 1988) (Kanters, Schouten et al, 1992) fairly short N--H distances of 0.94 (6) and 0.97 (6)A for two independent DMANH ÷ ions are found.…”

Section: Commentmentioning

confidence: 80%

“…One of the major reasons for the high level of basicity of these proton sponges in general and 1,8-bis(dimethylamino)naphthalene (DMAN) in particular, is the high degree of stability of the intramolecular [N--H...N] ÷ hydrogen bond of the protonated form of DMAN. The location and the possible disorder of this hydrogen bond in DMANH ÷ has been the focus of a number of studies (Llamas-Saiz et al, 1994, and references therein).…”

Section: Commentmentioning

confidence: 99%

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1,8-Bis(dimethylamino)naphthalene bis[6-fluoro-2-(trifluoromethyl)-4-quinolinol] acetonitrile solvate

Vergeer¹,

Kooijman²,

Schreurs³

et al. 1999

Acta Crystallogr C

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Section: Commentmentioning

confidence: 80%

Section: Commentmentioning

confidence: 99%

1,8-Bis(dimethylamino)naphthalene bis[6-fluoro-2-(trifluoromethyl)-4-quinolinol] acetonitrile solvate

Vergeer¹,

Kooijman²,

Schreurs³

et al. 1999

Acta Crystallogr C

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“…Conformation-controlling intramolecular interactions in drug molecules have a direct influence on the binding modes of the drugs with the respective targets [53,54,55]. In particular, intramolecular peri-interactions have been widely studied in the literature in naphthalene and other related systems [56][57][58][59][60].…”

Section: The Importance In Drug Design Of Similar To Hb Bondsmentioning

confidence: 99%

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Yunta¹

2017

AJMO

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The effect of weak intermolecular interactions on the binding affinity between ligand-protein complexes plays an important role in stabilizing a ligand at the interface of a protein structure. In this review article, we will explore the different ways of taking into account these interactions, mainly intramolecular hydrogen bonds, in docking calculations. Their possible limitations and their suitable application domains are highlighted. Inspection of the outliers of this study probed very stimulating, as it provides opportunities and inspiration to medicinal chemists, being a reminder of the impact that minimal chemical modifications can have on biological activities.

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“…These possibilities are demonstrated clearly by the successful synthesis of the hydrothermally stable ITQ-51 containing 1D 16-ring pores. The ability to design proton sponges with different sizes, geometries, hydrophobicity, or basicity (27,28) may open opportunities for the synthesis of new zeolitic materials. Moreover, we have demonstrated a complete ab initio 3D structure solution of unknown zeolites from a single submicrometersized crystal using the RED method.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of an extra-large molecular sieve using proton sponges as organic structure-directing agents

Martínez-Franco

Moliner

Yun

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

109

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The synthesis of crystalline microporous materials containing large pores is in high demand by industry, especially for the use of these materials as catalysts in chemical processes involving bulky molecules. An extra-large-pore silicoaluminophosphate with 16-ring openings, ITQ-51, has been synthesized by the use of bulky aromatic proton sponges as organic structure-directing agents. Proton sponges show exceptional properties for directing extra-large zeolites because of their unusually high basicity combined with their large size and rigidity. This extra-large-pore material is stable after calcination, being one of the very few examples of hydrothermally stable molecular sieves containing extra-large pores. The structure of ITQ-51 was solved from submicrometer-sized crystals using the rotation electron diffraction method. Finally, several hypothetical zeolites related to ITQ-51 have been proposed.aluminophosphate | extra-large microporous materials | zeolite synthesis

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Proton sponges

Cited by 221 publications

References 68 publications

1,8-Bis(dimethylamino)naphthalene bis[6-fluoro-2-(trifluoromethyl)-4-quinolinol] acetonitrile solvate

1,8-Bis(dimethylamino)naphthalene bis[6-fluoro-2-(trifluoromethyl)-4-quinolinol] acetonitrile solvate

It Is Important to Compute Intramolecular Hydrogen Bonding in Drug Design?

Synthesis of an extra-large molecular sieve using proton sponges as organic structure-directing agents

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