The role of micellar catalysis from kinetic and thermodynamic investigations of the reaction between bromhexine drug with para-dimethylaminobenzaldehyde

Khalil, Rabah A.; Saeed, Abdussamed

doi:10.1016/j.colsurfa.2006.10.064

Cited by 7 publications

(10 citation statements)

References 7 publications

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“…Thus, the different colors shown by species (6) from both (5) and (2) involved in the equilibrium of Scheme 2 allows the use of compound (2) as an acid-base indicator, placing the transition interval between pH 9.5 (yellow) and pH 10.5 (colorless). The yellow color of the reagent (2) in neutral state may be attributed to the conjugation as illustrated by the resonance structures of Scheme 3.…”

Section: Resultsmentioning

confidence: 99%

“…For this purpose, the Schiff base must possess a specific substituent at definite position to prevent its hydrolysis. In our investigations, we have found that the presence of sulfonamide group in the para-position of imine nitrogen is responsible for the indicator characteristics of the presented reagent (2). It should be noted that the use of acid-base indictor is not captured by titration method but also used to adjust the fine pH through pH indicator paper and the color of solution.…”

Section: Discussionmentioning

confidence: 99%

“…More *Corresponding author. E-mail: rakhalil64@yahoo.com recently, we have extended our investigations of the above reaction through using bromhexine drug [2,3] and three ȕ-lactams antibiotics [4] instead of sulfonamide. The colored solutions of these molecules do not show the above observed phenomenon of sulfanilamide.…”

Section: Introductionmentioning

confidence: 99%

“…The colored solutions of these molecules do not show the above observed phenomenon of sulfanilamide. Therefore, it seems quite interesting to synthesis the Schiff base from condensation of (1) with DAB and then separate it in a bulk form as 4[(4-dimethylamino-benzylidene)-amino]-benzene sulfonamide (2). This is followed by the study of its acid-base equilibrium in order to establish whether it could be used as an acid-base indicator.…”

Section: Introductionmentioning

confidence: 99%

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Application of a Schiff base derived from sulfanilamide as an acid-base indicator

Khalil

Jalil

Abd-Alrazzak

2009

JICS

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The present paper firstly announces the possibility of using a Schiff base as an acid-base indicator. This surprising phenomenon can be considered as an interest due to the fact that Schiff bases are usually unstable in solutions and definitely undergo hydrolysis. It was found that such a specific observation depends merely upon the chemical structure and type of the substitute of amine that reacts with aldehyde to give the Schiff base. The latter reagent 4[(4-dimethylamino-benzylidene)-amino]-benzene sulfonamide was synthesized from the condensation of sulfanilamide with p-dimethylaminobenzaldehyde. The reagent solution shows a reproducible change in its color due to the addition of acid and base. A UV-Vis spectroscopic characterization and acid-base equilibrium study of the reagent for its possible use as an indicator were investigated. The results show that the reagent is an amphoteric which possesses four ionization constants K a1 , K a2 , K b1 and K b2 of weak dibasic and diacidic properties. The value of pK a2 (9.80) is parallel to the observed transition interval pH 9.5 (yellow) and pH 10.5 (colorless), which is considered to be the indicator exponents pK i . It was concluded that the benzyl sulfonamide group plays a key role in the stability of the reagent towards hydrolysis and also for indicator characteristics through breaking the conjugation.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Application of a Schiff base derived from sulfanilamide as an acid-base indicator

Khalil

Jalil

Abd-Alrazzak

2009

JICS

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“…Indeed, our extensive study about the effect of SDS upon the kinetic and thermodynamic aspects of the presented reaction between bromhexine and DAB 15,16 led to a breakthrough with the presented procedure. The results of these investigations indicate that the molar ratio of bromhexine to DAB is 1:1.…”

Section: Resultsmentioning

confidence: 98%

Colorimetric Microdetermination of Bromhexine Drug in Aqueous Solution

Khalil

Saeed

2007

J Chinese Chemical Soc

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A simple, accurate and sensitive method for determination of bromhexine hydrochloride drug in aqueous solution has been described. The procedure has been based on the reaction of this drug with an excess amount of p-dimethylaminobenzaldehyde (DAB) in acidic medium (pH = 1.6) and the presence of sodium dodecyl sulfate (SDS). The produced yellow color from this reaction has been followed spectrophotometrically at an absorbance maximum of 430 nm. Microgram amounts of bromhexine hydrochloride can be estimated with an accuracy of better than ±1.5% and a relative standard deviation of less than 3.5%. The method has been used for the determination of 0.41-82.5 mg.mL -1 with a molar extinction coefficient of 4699.1-3602.3 L.mol -1 .cm -1 . An application of the developed procedure to bulk bromhexine hydrochloride and some of its pharmaceutical preparations has been carried out. The effect of the presence of some other surfactants and common pharmaceutical additives has been investigated. A comparison of the presented method with that in the absence of SDS and the standard method of the British Pharmacopoeia has been explored. The suggestion, according to the results, is to use the developed method as standard in pharmaceutical applications.

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Development of a Sensitive and Selective Method for the Determination of some Selected Aldehydes Based on Fluorescence Quenching

2023

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The role of micellar catalysis from kinetic and thermodynamic investigations of the reaction between bromhexine drug with para-dimethylaminobenzaldehyde

Cited by 7 publications

References 7 publications

Application of a Schiff base derived from sulfanilamide as an acid-base indicator

Application of a Schiff base derived from sulfanilamide as an acid-base indicator

Colorimetric Microdetermination of Bromhexine Drug in Aqueous Solution

Development of a Sensitive and Selective Method for the Determination of some Selected Aldehydes Based on Fluorescence Quenching

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