Proton magnetic resonance spectra of some naphthalene derivatives

Freeman, Harold S.; Hsu, Whei Neen; Esancy, James F.; Esancy, Michelle K.

doi:10.1016/0143-7208(88)85005-8

Cited by 14 publications

(6 citation statements)

References 13 publications

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“…Instead, a downÐeld shift to 7.09 ppm takes place, in the direction of the d(H2) of naphthalene (7.48 ppm, Table 4). 38 This observation has been explained by the electronic decoupling of the dimethylamino and naphthyl moieties in 1DMAN, caused by its larger twist angle (60¡) as compared with 1MAN and 1AN. A similar behaviour is found here (Table 4) for the series 14DMCN, 14MCN and 14ANCN, for which d(H2) equals 6.97, 6.53 and 6.72 ppm, respectively.…”

Section: H Nmr Spectramentioning

confidence: 99%

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Suzuki

Demeter

Kühnle

et al. 2000

Phys. Chem. Chem. Phys.

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Section: H Nmr Spectramentioning

confidence: 99%

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Suzuki

Demeter

Kühnle

et al. 2000

Phys. Chem. Chem. Phys.

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“…By analogy with naphthalene therefore, the signals at 7.92 pprn could be tentatively assigned to the proton on C-1 (and C-8) and the signals at 7.20 pprn can be assigned to the proton on C-3 (and C-6). Nevertheless, the assignment of chemical shifts using only the arguments made above or those made by Freeman et al (12) is clearly not sufficient for a multi-substituted naphthalene derivative such as CTA.…”

Section: Resultsmentioning

confidence: 93%

“…Lajunen et al (11) reported a 13C NMR study of CTA, but the 13C NMR spectrum was not definitively assigned. More recently, Freeman et al (12) described the 250-MHz 'H NMR spectrum of CTA and other naphthalene-based dyestuff intermediates '~u t h o r to whom correspondence may be addressed.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of chromotropic acid. ¹H and ¹³C NMR spectroscopy of chromotropic acid and its derivatives

Georghiou¹,

Ho²,

Jablonski³

1991

Can. J. Chem.

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. J. Chem. 69, 1207 (1991).The 'H and I3C NMR spectra of chromotropic acid (CTA) (4,5-dihydroxy-2,7-naphthalenedisulphonic acid) have been unambiguously assigned. Proton NOED spectra were used to show the proximity of both H-3 and H-6 and the hydroxyl groups. Two-dimensional 'H-'~c NMR correlation spectra of CTA, of its corresponding diacetoxy derivative, and of 3-bromo-and 3,6-dibromo-CTA support the assignments. A regioselective deuterium exchange reaction of the C-3 and C-6 protons of CTA with deuterium oxide was observed during the NMR experiments. This latter finding is strongly indicative of the mode of formation, and of the nature of the chromogen formed in the reaction of CTA with formaldehyde in the well-known CTA-formaldehyde analytical reaction.

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“…Manufactured from coal tar, a by-product of the coking process, it is routinely converted to phthalic anhydride, a compound essential to the manufacture of many commercial solvents and plastics [3]. Naphthalene is easily modified via electrophilic aromatic substitution reactions; analogs that are substituted with combinations of strongly electron-donating functional groups, such as alcohols and amines, are intermediates in the preparation of many synthetic dyes [4].…”

Section: Introductionmentioning

confidence: 99%

Degradative-release as a function of drug structure from LDI-glycerol polyurethanes

Sivak

Zhang

Pètoud

et al. 2010

Bio-Medical Materials and Engineering

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Naphthalene analogs with differing hydroxyl and amine functionality were incorporated into degradable polyurethane foams synthesized from lysine diisocyanate and glycerol to determine if chemical structure can be used in controlled release systems. Excitation and emission spectra of the various naphthalene analogs in aqueous solution were collected to ensure they were capable of being quantitatively detected in aqueous solution at low concentrations. The fluorescence stability of the compounds was assessed over a 2-week period at 70 • C; the analogs were all found to exhibit signal decay to varying degrees. Polyurethane foam materials containing the naphthalene analogs were synthesized and examined via scanning electron microscopy; incorporating naphthalene ligands did not grossly alter the polyurethane morphology. The analog distribution was then assessed via fluorescence microscopy, and the naphthalene analogs were found evenly dispersed throughout the polyurethane materials. Foam samples containing various analogs were then incubated in PBS buffer solution (pH 7.4) at 4, 22, 37 and 70 • C for 11-weeks. Temperature dependent release of naphthalene analogs from the polyurethane foams was found to depend upon the functional groups present on the naphthalene analog. These results suggest that the chemical structure of a drug plays a unique role in controlling release from hydrolytically degradable drug delivery systems.

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Proton magnetic resonance spectra of some naphthalene derivatives

Cited by 14 publications

References 13 publications

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Chemistry of chromotropic acid. ¹H and ¹³C NMR spectroscopy of chromotropic acid and its derivatives

Degradative-release as a function of drug structure from LDI-glycerol polyurethanes

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Proton magnetic resonance spectra of some naphthalene derivatives

Cited by 14 publications

References 13 publications

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Internal conversion in 4-substituted 1-naphthylamines. Influence of the electron donor/acceptor substituent character

Chemistry of chromotropic acid. 1H and 13C NMR spectroscopy of chromotropic acid and its derivatives

Degradative-release as a function of drug structure from LDI-glycerol polyurethanes

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Chemistry of chromotropic acid. ¹H and ¹³C NMR spectroscopy of chromotropic acid and its derivatives