Ethyl Aniline Research Articles

Thermodynamic properties of the hydrogen bonded complexes between N-substituted anilines and proton acceptors

The influence of temperature, within the range 285–340 K, on spectral characteristics of ν(NH) absorption bands in ‘free’ N -methyl aniline, N -ethyl aniline, diphenylamine and N -methyl-4-nitroaniline in CCl 4 as well as in their hydrogen bonded complexes with acetonitrile, tetrahydrofurane, dimethylformamide (DMF), dimethylsulfoxide (DMSO) and hexamethylphosphoramide (HMPA) was studied. Spectral moments of ν(NH) absorption bands were determined: M (0) —the zero spectral moment (integrated intensity), M (1) —the first spectral moment (the centre of band gravity), M (2) —the second central moment as well as ‘effective’ half width of absorption band (Δν 1/2 ) eff =2( M (2) ) 1/2 . The coefficients of the linear correlation of these parameters with a temperature variation Y = aT + b ( Y = M (0) , M (1) , 2( M (2) ) 1/2 ) were calculated for ‘free’ and hydrogen-bonded molecules. It was demonstrated that these spectral characteristics considerably depend on the character of the N-substitute. The difference in the position of absorption bands ν m (NH) in the spectra for non-bonded molecules of N-substituted anilines in CCl 4 is caused by σ–π conjugation of alkyl radicals with the N atom and substitute polarization influence. Thermodynamic parameters −Δ H and Δ S of the complex formation process between amines and proton acceptors were determined from the temperature dependence of the equilibrium constants on the basis of van't Hoff equation. The increase of −Δ H enthalpy was observed in the rows of proton donors: N -alkyl-substituted anilines, diphenylamine and N -methyl-4-nitroaniline; and proton acceptors: acetonitrile, tetrahydrofurane, DMF, DMSO and HMPA. The correlations between −Δ H values and the shift of the first spectral moment Δ M c (1) = M m (1) − M c (1) , on the one hand, and −Δ H values and the increment of the square root of integrated intensity Δ B 1/2 = B c 1/2 − B m 1/2 , on the other hand, were found on passing from free to bonded molecules. However, the proportionality factor α in the equation −Δ H =αΔ B 1/2 depends on individual characteristics of proton donors and remains the same for each proton donor in the row of proton acceptors.

Role of and Criterion for Sorption Selectivity in Pervaporative Removal of Trace Organics from Aqueous Solutions

Pervaporative separation of trace organics from aqueous solutions was studied using poly(dimethyl siloxane) (PDMS) membrane at compositions up to saturation concentration of organics. The organics compounds studied were allyl isothiocyanate (AITC), 1-butanol, 2-phenyl ethyl alcohol (PEA), benzyl alcohol, aniline, benzaldehyde, nitrobenzene, and carbon tetrachloride. Except for AITC, all other compounds were found to yield high permeation selectivity. Effects of various approaches of solubility parameter approach were found to be most satisfactory in predicting permeation selectivity in terms of sorption behavior in the solute–solvent–polymer ternary system.

Metabolism of metolachlor by fungal cultures.

Metabolism of metolachlor was studied using a mixed fungal culture isolated from a metolachlor-acclimated field soil. The culture rapidly degraded metolachlor with a half-life of 3.5 days in broth. Aspergillus flavus and A. terricola purified from the mixed culture also metabolized metolachlor effectively. Five metabolites obtained were identified by co-chromatography on HPLC by comparing with authentic standards and by GC-MS. Hydrolytic dechlorination, N-dealkylation, and amide bond cleavage appeared to be the dominant transformations involved in the metabolism. Metabolites, 6-methyl 2-ethyl acetanilide and 6-methyl 2-ethyl aniline, identified in this study are new metabolites of metolachlor being reported from any mixed or pure microbial cultures. The mixed culture could degrade 99% of metolachlor at a fortification level as high as 100 microg mL(-)(1).

Structural, morphological and spectroelectrochemical characterization of poly (2-ethyl aniline)

In this paper a comparative study of the structure, morphology, and the spectroelectrochemical response of poly (2-ethyl aniline) and polyaniline for different counterions is presented. Spongeous structure of poly (2-ethyl aniline) is obtained when mineral acids are used, while homogeneous and compact films are formed using organic acids. The electrochemical response of poly (2-ethyl aniline) depends on the charge/size ratio of the counterion due to both steric and electronic effects. The correlation between the absorption bands and the redox couple show that the changes in absorbance are proportional to the faradaic current observed in the voltammograms.

Synthesis of (+)-(R)-6-Ethyl-2,3-dihydro-2-methyl-4Hpyran-4-one -Sex-Pheromone Component of the Male Swift MothHepialus hectaL

Abstract The synthesis of the male swift moth sex pheromone component, (+)-(R)-6-ethyl-2,3-dihydro-2-methyl-4H-pyran-4-one (6), from ethyl aniline and (S)-2-methyloxirane is described.

Castor oil as a way to fast-cured polyurethane ureas

Polyurethane urea networks have been synthesized in bulk from castor oil, isophorone diisocyanate and methylene bis-methyl ethyl aniline. The kinetics of prepolymer formation have been studied by gel permeation chromatography. Calorimetric and dynamic mechanical properties have been studied for various stoichiometric ratios. A wide range of moduli can be obtained, with short reaction times.

Hemicyanines from 3-arylbenzo [f] quinolinium salts and their spectral-luminescence properties

1-(β-Anilinovinyl)-3-arylbenzo[f]quinolinium methiodides were synthesized by the condensation of 1,4-dimethyl-3-arylbenzo[f]quinolinium salts with ethyl orthoformate and aniline or by fusion with N,N-diphenylformamidine. The IR spectra, the absorption spectra in the visible region, and the fluorescence of the dyes in the crystalline state were examined. The introduction of substituents in the 3-phenyl ring of benzo[f]quinoline gives rise to a bathochromic shift of the fluorescence band.

Chemistry of nitropyrroles

1. A study was made of the reactions of the dipotassium salt of trinitropropionaldehyde with formaldehyde and a primary amine, those examined being benzylamine, 2-aminoethanol, glycine ethyl ester, aniline, ammonia, hydrazine, ethylenediamine, and urea. 2. The reactions with benzylamine, 2-aminoethanol, and glycine ethyl ester led to the formation of the corresponding nitropyrrole derivatives: 1-benzyl-3,4-dinitropyrrole, 1-(2-hydroxyethyl)-3,4-dinitropyrrole [3,4-dinitropyrrole-1-ethanol], and ethyl 3,4-dinitropyrrole-1-acetate. In the case of ammonia, hydrazine, ethylenediamine, and urea the reaction did not go in the desired direction. 3. In the reaction with aniline two individual substances C16H13N3O2 and C13H11N3O2 were obtained; their structures were not determined. 4. It was shown that simple homologs of formaldehyde can be used in the reaction, namely acetaldehyde and propionaldehyde.

CONTRIBUTION TO THE STUDY OF 1,1-DIPHENYLINDAN AND ITS DERIVATIVES. SYNTHESIS OF 1,1-DIPHENYL-3-INDANACETIC AND 1,1-DIPHENYL-3-INDENEACETIC ACIDS

1,1-Diphenylindan was treated with one molecule of bromine. It yielded a monobromide, which was condensed with methyl and ethyl alcohols, piperidine, p-toluidine, and aniline. With aqueous solutions of potassium carbonate, the monobromide directly gave rise to 1,1-diphenylindene and small quantities of diphenylindanyl ether.The condensation of the monobromide with sodium ethyl malonate yielded ethyl 1,1-diphenyl-3-indanmalonate from which 1,1-diphenyl-3-indanmalonic and 1-1-diphenyl-3-indanacetic acids were prepared. A few derivatives of these acids were also obtained.To establish the constitution of 1,1-diphenyl-3-indanacetic acid and, hence, that of the monobromide and of the other compounds, this acid was prepared directly from 3,3-diphenyl-1-indanone by a Reformatsky reaction with ethyl bromoacetate.The method of preparation of 1,1-diphenylindan has been improved, 1,1-diphenylindene has been obtained by new methods, and the following compounds are described, as far as the authors are aware, for the first time: 3-bromo-1,1-diphenylindan, 3-methoxy-1,1-diphenylindan, 3-ethoxy-1,1-diphenylindan, 3-N-piperidyl-1,1-diphenylindan, N-phenyl-1,1-diphenyl-3-indanamine, N-p-tolyl-1,1-diphenyl-3-indanamine, ethyl 1,1-diphenyl-3-indanmalonate, 1,1-diphenyl-3-indanmalonic acid, 1,1-diphenyl-3-indanmalonic acid p-nitrobenzyl ester, silver salt of 1,1-diphenyl-3-indanmalonic acid, 1,1-diphenyl-3-indanacetic acid, 1,1-diphenyl-3-indanacetic acid p-nitrobenzyl ester, silver salt of 1,1-diphenyl-3-indanacetic acid, 1,1-diphenyl-3-indanacetanilide, 1,1-diphenyl-3-indanacetamide, 1,1-diphenyl-3-indanacetonitrile, 1,1-diphenyl-3-indanethylamine hydrochloride, ethyl 3-hydroxy-1,1-diphenyl-3-indanacetate, ethyl 1,1-diphenyl-3-indeneacetate, 1,1-diphenyl-3-indeneacetic acid, silver salt of 1,1-diphenyl-3-indeneacetic acid, 1,1-diphenyl-3-indeneacetic acid p-nitrobenzyl ester, ethyl 1,1-diphenyl-3-indanacetate.