ACCURATE CALCULATION OF PKA OF SULFACETAMIDE USING HIGH-LEVEL AB INITIO CALCULATIONS

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AJAMEIN H.; NAMAZIAN M.; Noorbala m.r.; TAMADON F.

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Seminar: IRANIAN CHEMISTRY CONGRESS
Year:2013 | Issue:16

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Title

ACCURATE CALCULATION OF PKA OF SULFACETAMIDE USING HIGH-LEVEL AB INITIO CALCULATIONS

Author(s)

AJAMEIN H. | NAMAZIAN M. | Noorbala m.r. | TAMADON F. | Issue Writer Certificate

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Abstract

THE SULFONAMIDE–SO2NH– GROUP EXISTS IN NUMEROUS BIOLOGICALLY ACTIVE COMPOUNDS, WHICH INCLUDE ANTIMICROBIAL DRUGS, SALURETICS, CARBONIC ANHYDRASE INHIBITORS, INSULIN-RELEASING SULFONAMIDES, ANTITHYROIDAGENTS ANTITUMOR DRUGS. SULFACETAMIDE IS A SULFONAMIDE ANTIBIOTIC THAT BLOCKS THE SYNTHESIS OF DIHYDROFOLIC ACID BY INHIBITING THE ENZYME DIHYDROPTEROATE SYNTHASE. SULFACETAMIDE IS A COMPETITIVE INHIBITOR OF BACTERIAL PARA-AMINOBENZOIC ACID (PABA), WHICH IS REQUIRED FOR BACTERIAL SYNTHESIS OF FOLIC ACID [1]. THE ACID-BASE PROPERTIES OF THESE COMPOUNDS ARE BELIEVED TO PLAY AN IMPORTANT ROLE IN THEIR BIOLOGICAL ACTIVITIES. SULFACETAMIDE HAS AN–NH2 GROUP AND–NHCOCH3 GROUP WHICH PRESENT BASIC AND ACIDIC PROPERTIES, RESPECTIVELY. THIS MOLECULE ALSO HAS A CHANCE TO BE IN THE FORM OF ZWITTERION.IN THE PRESENT RESEARCH, WE STUDIED THEORETICALLY THE STABILITY OF SULFACETAMIDE IN DIFFERENT FORMS IN BOTH GAS-PHASE AND AQUEOUS SOLUTION. WE FOUND THAT ZWITTERION IS NOT THE MOST STABLE FORM FOR THIS MOLECULE. THE ACIDITY AND BASICITY OF THIS COMPOUND HAVE BEEN ALSO INVESTIGATED. THE THEORETICAL PKA OF THIS MOLECULES HAS BEEN CALCULATED AS 4.9 WHICH IS IN AGREEMENT WITH THE EXPERIMENTAL VALUE OF 5.4 [2].IN THIS WORK, STANDARD AB INITIO MOLECULAR ORBITAL THEORY AND DENSITY FUNCTIONAL THEORY CALCULATIONS WERE CARRIED OUT USING THE GAUSSIAN 09 SOFTWARE. GEOMETRIES OF ALL SPECIES WERE OPTIMIZED AT THE B3LYP/6-31G (D) LEVEL OF THEORY, AND WHERE NECESSARY, EXTRA CARE WAS TAKEN TO SELECT THE MINIMUM-ENERGY CONFORMATION VIA SYSTEMATIC CONFORMATIONAL SEARCHING AT THIS LEVEL. THE NATURE OF EACH STATIONARY POINT WAS ESTABLISHED VIA B3LYP/6-31G (D) FREQUENCY CALCULATIONS. THE OPTIMIZED GEOMETRIES HAVE BEEN USED FOR FURTHER CALCULATIONS. FOR CALCULATION OF ENERGIES, ENTHALPIES AND GIBBS ENERGIES, G3 (MP2) //B3LYP [3] HAS BEEN USED ALONG WITH AVAILABLE SOLVATION MODELS OF CPCM AND SMD [4].

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APA: Copy

AJAMEIN, H., NAMAZIAN, M., Noorbala, m.r., & TAMADON, F.. (2013). ACCURATE CALCULATION OF PK_A OF SULFACETAMIDE USING HIGH-LEVEL AB INITIO CALCULATIONS. IRANIAN CHEMISTRY CONGRESS. SID. https://sid.ir/paper/915781/en

Vancouver: Copy

AJAMEIN H., NAMAZIAN M., Noorbala m.r., TAMADON F.. ACCURATE CALCULATION OF PK_A OF SULFACETAMIDE USING HIGH-LEVEL AB INITIO CALCULATIONS. 2013. Available from: https://sid.ir/paper/915781/en

IEEE: Copy

H. AJAMEIN, M. NAMAZIAN, m.r. Noorbala, and F. TAMADON, “ACCURATE CALCULATION OF PK_A OF SULFACETAMIDE USING HIGH-LEVEL AB INITIO CALCULATIONS,” presented at the IRANIAN CHEMISTRY CONGRESS. 2013, [Online]. Available: https://sid.ir/paper/915781/en

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