Amfiprotik ve Dipolar Aprotik Çözücülerde 3-(4-Aril) Propiyonik Asit Türevlerinin Asitlik Kuvvetleri

Yıl 2020, , 1876 - 1885, 01.09.2020

Zafer Ocak

https://doi.org/10.21597/jist.675630

Cited By: 1

Öz

Beş adet 3-(4-aril) propiyonik asit türevinin asitlik özellikleri incelenmiştir. Bu çalışmada amfiprotik çözücülerden etanol, tert‐butanol ve su, dipolaraprotik çözücülerden N,N dimetilformamid (DMF), aseton kullanılmıştır. Bileşikler tetrabutilamonyum hidroksidin (TBAH) metanoldeki çözeltisi ile titre edilmiş ve titrasyonlarda dönüm noktasının belirlenmesinde potansiyometrik metod, asitliğin belirlenmesinde yarı nötralizasyon metodu kullanılmıştır. Titrasyon eğrilerinin beklendiği gibi S şeklinde olduğu belirlenmiştir. Çizelge ve grafikler kullanılarak propiyonik asit türevlerinin amfiprotik ve dipolar aprotik çözücülerdeki asitlik kuvvetleri hesaplanmıştır. Çözücülerde elde edilen pKa değerlerinin farklandırıldığı görülmüştür. Bileşiklerin asitlik kuvvetlerine çözücü, moleküler yapı, otoprotoliz sabiti, dielektrik sabiti ve çözücünün seviyeleme-farklandırma etkileri tartışılmıştır.

Anahtar Kelimeler

3-(4-aril)propiyonik asit, amfiprotik çözücü, asitlik kuvveti, yarı nötralizasyon metodu

Destekleyen Kurum

yok

Proje Numarası

yok

Teşekkür

yok

The Acidity Strengths of 3-(4-Aryl) Propionic Acid Derivatives in Amphiprotic and Dipolar Aprotic Solvents

Öz

The acidic properties of five 3-(4-aryl) propionic acid derivatives were investigated. In this study, ethanol, tert‐butanol and water were used as an amphiprotic solvent. Aceton and N,N‐dimethylformamide (DMF) were preferred as a dipolar aprotic solvent. Compounds were titrated with tetrabuthylamonnium hydroxide (TBAH) in methyl alcohol and titrimetric analyses were used potentiometric method determining the end-points, half-neutralization method determining acidity. Typical S-shaped titration graphs excepted were determined. The acidity strengths of propionic acid derivatives in amphiprotic and dipolar aprotic solvents were calculated using tables and graphs. The pKa values obtained in the solvents were found to be differentiated. The effects of solvent, molecular structure, autoprotolysis constant dielectric constant, and leveling‐differentiation effects of the solvents upon acidity strength of the compounds were discussed.

Anahtar Kelimeler

Amphiprotic solvent, 3-(4-aryl) propionic acid, Acidity strength, Half‐neutralization method

Proje Numarası

yok

Kaynakça

• Alkan M, Gürbüz A, Yüksek H, Gürsoy Kol Ö, Ocak Z, 2014. Synthesıs and Non-Aqueus Medıum Tıtratıons of Some New 3-Alkyl(Aryl)-4-[2-(4-Methoxybenzoxy)- 3-Methoxy]-Benzylidenamıno-4,5-Dıhydro-1H -1,2,4-Trıazol-5-Ones. Caucasian Journal of Science, 1: 138‐147.
• Almeida V R, Szpoganicza B, Bonnevilleb S, 2015. Potentiometric Titration and Out-Of-Equilibrium pH Response of the Biotite‑Water System. Journal of the Brazilian Chemical Society, 26 (9): 1848-1860.
• Amirdehi M A, Pousti M, Asayesh F, Gharib F, Greener J, 2017. Solvent Effects on Acid–Base Equilibria of Propranolol and Atenolol in Aqueous Solutions of Methanol: UV-Spectrophotometric Titration and Theory. Journal of Solution Chemistry, 46:720–733.
• Anonim, 2019. Propiyonik Asit ,(E280) https://ansiklopedi.halisinden.com/Propiyonik_Asit_(E280) (Erişim Tarihi:14.01.2020).
• Arslantaş A, Yüksek H, Gürsoy Kol Ö, Ocak Z, Tomruk Z, Calapoğlu M, 2012. Study of Antioxidant Properties and DNA Interaction of Some Novel 4,5-Dıhydro-1H -1,2,4-Trıazol-5-One Derivates. Asian Journal of Chemistry, 24(8): 3327‐3334.
• Bolong W, Fengxia Z, Xiaoning M, Fengjuan Z, 2016. Determination of Chloride in Infant Formula and Adult/Pediatric Nutritional Formula by Potentiometric Titration: Single-Laboratory Validation, First Action 2015.07. Journal of Association of Official Agricultural Chemists International, 99 (1): 198-203.
• Gündüz T, 2001. İnstrümental Analiz. Ankara Üniversitesi Fen Fakültesi Yayınları, s.936-940, Ankara-Türkiye.
• Hadjeb R, Barkat D, 2017. Determination of acid dissociation constants of some substituted salicylideneanilines by spectroscopy. Application of the Hammett relation. Arabian Journal of Chemistry, 10: S 3646–S3651.
• Hakli O, Ertekin K, Ozer M S, Aycan S, 2008. Determination of pKa Values of Clinically Important Perfluorochemicals in Nonaqueous Media. Journal of Analytical Chemistry, 63( 11): 1051–1056.
• Huang K, Xu Y, Lu W, Yu S, 2017. A Precise Method for Processing Data to Determine the Dissociation Constants of Polyhydroxy Carboxylic Acids via Potentiometric Titration. Applied Biochemistry and Biotechnology, 183:1426–1438.
• İslamoğlu F, Karaali N, Tanyel T, 2016. Calculation of Acid Dissociation Constants And Biological Activities In Some Pyrimidine Derivatives As Known Drug Active Substance. International Journal of Pharmaceutical,Chemical And Biological Sciences, 6(4):455-464.
• Katea A S, Basavaraju K C, 2018. A simple potentiometric titration method for estimation of maleic anhydride in high molecular weight styrene-maleic anhydride copolymer. Polymer Testing, 65: 369–373.
• Kiani F, Izadi H, Tahermansouri, Koohyar F, 2014. Determination of acidic dissociation constants of glutamine and isoleucine in water using ab initio methods. Türk Biyokimya Dergisi [Turkish Journal of Biochemistry–Turk J Biochem], 39(4): 503–515.
• Kumar S, Babu BV, 2006. A Brief Review on Propionic Acid: A Renewal Energy Source. Proceedings of National Conference on Environmental Conservation, Plani, September 1-3, 2006, pp: 459-464.
• Lisa T, Chansyanah D, Marina S, Nina K, Andrian S, 2019. Using Potentiometric Acid-Base Titration to Determine pKa from Mangosteen Pericarps Extract. Periódico Tchê Química, 16, 768-773.
• Loeppert R. H, Zelazny LW, Volk B. G,1979. Titration of pH-Dependent Sites of Kaolinite In Water and Selected Nonaqueous Solvents. Clays and Clay Minerals, 27 (1): 57-62.
• Meloun M, Bordovska S, Syrovy T, 2007. A novel computational strategy for the pKa estimation of drugs by non-linear regression of multiwavelength spectrophotometric pH-titration data exhibiting small spectral changes. Journal of Physical Organic Chemistry, 20: 690–701.
• Ocak Z, 2018. Solvent and moleculer structure effect on the acidity of 2-furoic acid derivatives. 1st International Balkan Chemistry Congress, Edirne, Septemper 17-21, pp:40.
• Özil M, İslamoğlu F, Menteşe F, Kahveci B, 2010. Microwave‐Assisted Synthesis of Novel 2,4‐Dihydro‐5‐[4‐(trifluoromethyl)phenyl]‐3H‐1,2,4‐triazol‐3‐ones and Potentiometric Determination of Their pKa in Nonaqueous Solvents. Helvetica Chimica Acta, 93(10): 1967-1974.
• Pilarski B, Kaliszan R,Wyrzkowski D, Mlodzianowski J, Balinska A, 2015. General Analytical Procedure for Determination of Acidity Parameters of Weak Acids and Bases. Journal of Analytical Methods in Chemistry, 1- 8.
• Reijenga J, Hoof A, Loon A, Teunissen B, 2013. Development of Methods for the Determination of pKa Values. Analytical Chemistry Insights, 8: 53–71.
• Taskiran D T, Urut GÖ, Ayata S, Alp S, 2017. Spectrofluorimetric and Potentiometric Determination of Acidity Constants of 4-(4′-Acetyloxy-3′-Methoxybenzylidene)- 5-Oxazolone Derivatives. Journal of Fluoresc, 27:521–528.
• Yokuş Ö A, Yüksek H, Kol Ö G, Karaoğlu Ş A, 2015. Synthesis and Biological Evaluation of New 1,2,4-triazole Derivatives with Their Potentiometric Ttrations. Medicinal Chemistry Research, 24:2813–2824.
• Yüksek H, Akyildirim O, Kol Ö G, 2013. Synthesis and In Vitro Antioxidant Evaluation of New 1,3,5-Tri- {2-methoxy-4-[(4,5-dihydro-1𝐻-1,2,4-triazol-5-on-4-yl)-azomethine]-phenoxycarbonyl}-Benzene Derivatives. Journal of Chemistry, 1–8.
• Yüksek H, Küçük M, Alkan M, Bahçeci Ş, Kolaylı S, Ocak Z, Ocak U, Şahinbaş E, Ocak M, 2006. Synthesis and Antioxidant Activities of Some New 4-(4-Hydroxy-benzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives with Their Acidic Properties. Asian Journal of Chemistry, 18(1):539-550.
• Zafar S, Akhtar S, Tariq T, Mushtag N, Akram A, Ahmed A, Arif M, Naeem S, Anwar S,2014. Determination of pKa values of new phenacyl-piperidine derivatives by potentiometric titration method in aqueous medium at room temperature (25±0.5oC). Pakistan Journal of Pharmaceutical Sciences, 27 (4): 925-929.