Solid-state NMR and x-ray diffraction studies of ionic complex of 1,8-bis(dimethylamino)naphthalene (DMAN) with picrolonic acid

naik, Krzysztof Wo; Krygowski, Tadeusz M.; Pawlak, Dorota A.; Kolodziejski, Walaw; Grech, E.

doi:10.1002/(sici)1099-1395(199711)10:11<814::aid-pca953>3.0.co;2-s

Cited by 12 publications

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References 28 publications

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“…Interestingly, similar chemical shifts (approx. 17-18 ppm) have been described in the literature for the acidic proton shielded by the amino groups on different DMAN complexes with inorganic and organic acids [24][25][26][27][28]. The solid 1 H MAS NMR spectrum of commercially available DMAN only shows the two large peaks corresponding to protons bound to the aliphatic and aromatic carbons (figure 3a), but no signal at approximately 18.5 ppm is observed.…”

Section: Resultsmentioning

confidence: 90%

Supra-molecular assembly of aromatic proton sponges to direct the crystallization of extra-large-pore zeotypes

et al. 2014

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The combination of different experimental techniques, such as solid 13 C and 1 H magic-angle spinning NMR spectroscopy, fluorescence spectroscopy and powder X-ray diffraction, together with theoretical calculations allows the determination of the unique structure directing the role of the bulky aromatic proton sponge 1,8-bis(dimethylamino)naphthalene (DMAN) towards the extra-large-pore ITQ-51 zeolite through supra-molecular assemblies of those organic molecules.

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Section: Resultsmentioning

confidence: 90%

Supra-molecular assembly of aromatic proton sponges to direct the crystallization of extra-large-pore zeotypes

et al. 2014

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“…The NH bond in DMANH + is, however, substantially elongated due to the electrostatic interaction with the counterion. The latter forms an ion pair with DMANH + , approaching the cation near the place where the bridging proton is located, both in solids 15,16 and in liquids. 17 In porphycene, no ion pairs can be formed and, therefore, the NH bond can be better modeled by that in a protein.…”

Section: Resultsmentioning

confidence: 99%

Accurate determination of the ultrafast proton transfer rate in porphycene using nuclear spin relaxation

Bernatowicz

2013

Phys. Chem. Chem. Phys.

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The longitudinal (15)N relaxation rate and (15)N{(1)H} NOE enhancement were determined for porphycene in a CD2Cl2 solution. By invoking the rotational diffusion tensor of porphycene as previously determined, these data could be used to evaluate the tautomerization rate of protons in the NHN bridges. The proton transfer rate compares well to the results obtained by other authors by means of optical spectroscopy.

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Low-temperature (120 K) structure and vibrational spectrum of protonated proton sponge: the adduct of 1,8-bis(dimethylamino)naphthalene (DMAN) with 4,5- dicyanoimidazole (DCI)

Grech

Malarski

Sawka‐Dobrowolska

et al. 1999

J. Phys. Org. Chem.

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Low-temperature (120 K) studies of the structure of the DMAN Á DCI adduct indicate that in symmetrical [NHN] hydrogen bridge of 2.571 (1) Å length (2.579(2) Å at room temperature) there is a disorder of the H-atom occupying two positions at nitrogen atoms with a distance of 0.94(3) Å . The comparison with the situation at room temperature seems to show a very low barrier for the proton transfer. The low-frequency vibrations with the participation of the whole N(CH 3 ) 2 groups observed in Raman and inelastic incoherent neutron scattering (IINS) spectra of about 100 cm À1 excited at room temperature cause the fundamental level of the protonic mode to penetrate or exceed the barrier. The bending CNC vibrations of about 500 cm À1 are strongly coupled with the protonic mode leading to Evans holes in the band ascribed to the 0 → 0 À transition. This hypothesis is consistent with the literature data relating to theoretical studies on H 3 NHNH 3 , which show that the barrier for the proton transfer disappears at the hydrogen bond length of about 2.55 Å .

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Solid-state NMR and x-ray diffraction studies of ionic complex of 1,8-bis(dimethylamino)naphthalene (DMAN) with picrolonic acid

Cited by 12 publications

References 28 publications

Supra-molecular assembly of aromatic proton sponges to direct the crystallization of extra-large-pore zeotypes

Supra-molecular assembly of aromatic proton sponges to direct the crystallization of extra-large-pore zeotypes

Accurate determination of the ultrafast proton transfer rate in porphycene using nuclear spin relaxation

Low-temperature (120 K) structure and vibrational spectrum of protonated proton sponge: the adduct of 1,8-bis(dimethylamino)naphthalene (DMAN) with 4,5- dicyanoimidazole (DCI)

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