Synthesis and Potentiometric Titrations of Novel Di-{2-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethine]-6-methoxy}-phenyl Terephtalates

Abstract

In this study, 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) reacted with di-(2-formyl-6-methoxyphenyl) terephtalate (3), which was synthesized by the reaction of o-vanillin with terephthaloyl chloride by using triethylamine, to afford the corresponding seven novel di-{2-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethine]-6-methoxy}-phenyl terephtalates (4). The structures of new synthesized compounds were characterized by mains of elemental analysis and spectroscopic methods. In addition, to investigate the effects of solvents and molecular structure upon acidity, the prepared compounds 4 were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents, including acetone, 2-propanol, tert-butyl alcohol and N, N-dimethylformamide (DMF). The half-neutralization potential (HNP) values and the corresponding pKa values were determined.

Keywords

• 124-Triazol-5-one
• Syntheses
• Schiff base
• pKa
• Potentiometric titration

Yeni Di-{2-[(3-alkil)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]-6-metoksi}-fenil Tereftalat Bileşiklerinin Sentezi ve Potansiyometrik Titrasyonları

Öz

Bu çalışmada, 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (3) bileşiklerinin trietiamin varlığında o-vanillinin tereftaloil klorür ile reaksiyonundan elde edilen di-(2-formil-6-metoksifenil) tereftalat (3) ile reaksiyonundan yedi yeni di-{2-[(3-alkil)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]-6-metoksi}-fenil tereftalat (4) bileşikleri sentez edilmiştir. Sentezlenen yeni bileşikler elementel analiz ve spektroskopik yöntemlerle karakterize edilmiştir. Ayrıca, asitlik üzerine çözücü and molekül yapısının etkisini incelemek için, sentezlenen 4 tipi yeni bileşiklerin aseton, 2-propanol, tert-butanol ve N,N-dimetilformamid (DMF) susuz çözücüleri içerisinde tetrabutilamonyum hidroksit (TBAH) ile potansiyometrik titrasyon incelemeleri yapılmıştır. Her bileşik için kullanılan susuz çözücülerdeki yarı nötralizasyon potansiyel (HNP) değerleri ve karşın olan pKa değerleri tayin edilmiştir.

Anahtar Kelimeler

• Sentez
• Schiff bazı
• pKa
• Potansiyometrik titrasyon
• 124-Triazol-5-on

Kaynakça

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