96-77-5Relevant articles and documents
NMR Characterization of Sulfonation Products of Phenylchloroformate with Verification of NOE Effects by Molecular Modeling
Kwoh, David,Kerschner, Judith L.,Jensen, Arnold,Cece, Anthony
, p. 407 - 412 (1995)
In the trial scale-up of the sulfonation of phenylchloroformate and subsequent formation of sulfonated phenyl carbonates, samples from the batch process showed a number of unexpected by-products.Because they were suspected to have an unusual ring substitution pattern, phenylchloroformate sulfonation was studied by 1H and two-dimensional nuclear magnetic resonance (NMR) techniques.Distance geometry was used to compute internuclear distances, which were used to substantiate the observation of the nuclear Overhauser effect.The reaction mechanism leading to these by-products is proposed.Index Headings: Phenylchloroformate; Sulfonation; 1H NMR; Two-dimensional NMR; Potential energy computation.
A fluorescent molecule based on 1,8- naphthalic anhydride: Synthesis, spectral properties, and studying the conductance in solution
Al-Aqar, Roza
, p. 4227 - 4233 (2020/12/09)
In this paper, the compound of (4-bromo-3-nitro-1,8 -naphthalic anhydride) and the dopant material (4-hydroxy-m-benzene-disulfonic acid) were synthesized. The UV- Vis absorption and emission spectra of the compound were recorded. 4-bromo-1,8- naphthalic anhydride was used as a starting material to prepare the compound (4-bromo-3-nitro-1,8 -naphthalic anhydride) in the presence of concentrated sulphuric acid and sodium nitrate. The dopant material (4-hydroxy-m-benzene-disulfonic acid) was prepared by using phenol in concentrated sulfuric acid. The absorption bands depend on the solvent polarity, which the compound shows significant red shift in DMSO solvent compared to in ethanol solvent. The fluorescence spectra of this compound were sensitive to the solvent polarity, the calculated result indicates that the maximum peak is shifted to red in polar solvent, to the excited states of the polar ICT, which leads to decrease the energy of the excited states. The effect of the dopant material on the conductivities (ionic and specific) of the compound was studied, the ionic conductance was increased as the weight of the dopant material increases.
On the intermediacy of phenyl hydrogen sulfates in the sulfonation of phenols. Sulfonation of phenol, anisole, methyl phenyl sulfate, the 2-halogenophenols, a series of phenyl methanesulfonates together with 2,6-dimethylaniline and its N-methylsulfonyl derivative
de Wit, Peter,Woldhuis, Alex F.,Cerfontain, Hans
, p. 668 - 675 (2007/10/02)
The sulfonation of methyl phenyl sulfate (4) with concentrated aqueous sulfuric acid at 25 deg C yields the 4-sulfonic acid.This initial product then decomposes to give phenol-4-sulfonic acid, which is subsequently sulfonated to phenol-2,4-disulfonic acid.From the first-order-rate coefficients obtained for sulfonation of phenyl methanesulfonate (3) and (4) in 93,2percent H2SO4, for which acid concentration the sulfonating entity is H2S2O7, the ?p+ values of the OSO2Me and OSO2OMe substituents have been determined to be 0.40 and 0.46, respectively.The sulfonation of both 2-chlorophenyl (10) and 2-methylphenyl methanesulfonate (14) with 2.0 equiv of SO3 in nitromethane at 0.0 deg C yields the 4-sulfonic acid as the exclusive product, whereas 2-methoxyphenyl methanesulfonate (13), under the same conditions, forms exclusively the 5-sulfonic acid. 2-Chloro- (6), 2-bromo- (7) and 2-iodophenol (8) with 1.0 and 4.0 equiv of SO3 in nitromethane yield exclusively the 4-sulfonic acid, while 2-fluorophenol (5) with 2.0 and 5.0 equiv of SO3 yields in addition the 5-sulfonic acid to the extent of 4 and 30percent, respectively.In the reactions of 2,6-dimethylphenol (15) and 2,6-dimethylaniline (17) with at least 1 equiv of SO3 in nitromethane, the 3-SO3H/4-SO3H ratio was found to increase on increasing the relative amount of SO3.For both 15 and 17, the limiting 3-SO3H/4-SO3H ratio at high SO3/ArOH ratios is 86/14 and this value is considered to be the ratio for the sulfonation of both 2,6-dimethylphenyl hydrogen sulfate and 2,6-dimethylaniline-N-sulfonic acid.This assumption is supported by the observation that the sulfonation of 2,6-dimethylphenyl methanesulfonate (16) and N-(methylsulfonyl)-2,6-dimethylaniline (18) with SO3 leads to a similar 3-SO3H/4-SO3H ratio.
