Trietilamin varlığında bazı alifatik karboksilik asitlerden disübstitüe organosiklotrifosfazenlerin sentezi ve karakterizasyonu

Yıl 2020, Cilt: 22 Sayı: 2, 709 - 716, 10.04.2020

Orhan Pamukçu Fatih Aslan

https://doi.org/10.25092/baunfbed.757301

Öz

Organosiklotrifosfazen elde etmek için bazı alifatik karboksilik asitler ile hekzaklorosiklotrifosfazenin tepkimesi trietilamin varlığında THF çözücüsünde gerçekleştirildi. Asetik asit, bütirik asit, 4-kloro-sinnamik asit ve 4-kloro-fenil-asetik asit tepkimelerde alifatik karboksilik asit olarak kullanıldı. Bütün tepkimelerde oluşan trietilamonyum klorür miktarı, yer değiştiren iki mol klora karşılık geldiği belirlendi. Ayrıca, 18 ppm civarında ikili ve -12 ppm civarında üçlü iki pik bütün bileşiklerin (2-5) 31P NMR spektrumlarında görüldü. Elde edilen bu iki sonuca göre, sentezlenen organosiklotrifosfazenlerin gem-disubstitüe yapısında olduğu belirlendi. Bütün bileşiklerin yapıları gravmetrik ve spektroskopik yöntemlerle belirlendi. IR ve NMR (1H, 13C ve 31P) spektroskopileri bileşiklerin spektroskopik analizinde kullanıldı.

Anahtar Kelimeler

Fosfazen, organofosfazen, karboksilik asit

Teşekkür

Bu çalışmamız HÜBAK tarafından 14173 nolu proje ile desteklenmiştir.

Synthesis and characterization of disubstituted organocyclotriphosphazenes from some aliphatic carboxylic acids in the presence of triethylamine

Öz

The reaction of hexachlorocyclotriphosphazene with some aliphatic carboxylic acids was performed in THF solvent in the presence of triethylamine to obtain organocyclotriphosphazene. Acetic acid, butyric acid, 4-chloro-sinnamic acid and 4-chloro-phenyl-acetic acid were used as aliphatic carboxylic acid in the reactions. It was determined that the amount of triethylammonium chloride generated in all reactions corresponds to two equivalent of chlorine displaced. Additionally, two peaks were seen at around 18 ppm as doublet and around -12 ppm as triplet in the 31P NMR spectra of the compounds (2-5). According to these two results, the synthesized organocyclotriphosphazene derivatives were determined to be in the gem-disubstituted structure. The structures of all compounds were determined by gravimetric and spectroscopic methods. FTIR and NMR (1H, 13C and 31P) spectroscopies were used in spectroscopic analysis of the compounds.

Anahtar Kelimeler

Phosphazene, organophosphazene, carboxylic acid

Kaynakça

• Aslan, F., Ozturk, A.I., Soylemez, B., Synthesis of fluorescence organocyclotriphosphazene derivatives having functional groups such as formyl, Schiff base and both formyl and Schiff base without using Ar or N-2 atmosphere, Journal of Molecular Structure, 1137, 387-395, (2017).
• Hanife, İ., Güzel, A., Yüksel, F., The reaction of hexachlorocyclotriphosphazatriene with p-aminophenol, Phosphorus, Sulfur, and Silicon and the Related Elements,192, 92-97, (2017).
• Arslan, M., Aslan, F., Öztürk, A.I, Arylation reaction of N-dichlorophosphoryl-P-trichlorophosphazene, Heteroatom Chemıstry, 14, 138-143, (2003).
• Allcock, H. R. Phosphorue-Nitrogen Compounds, Academic Press (New York and London), 279- 281, (1972).
• Bezman, I. I., Reed,W. R., Nitrile Formation by Reaction of Triphosphonitrilic Chloride with Carboxylic Acid Salts, Journal of the American Chemical Society, 82, 2167-2168, (1960).
• Caglioti, L., Poloni, M., Rosini, G., Phosphonitrilic Chloride as Activator of Carboxylic Acids. Formation of Amides and Hydrazides, The Journal of Organic Chemistry, 99, 2979-2981, (1968).
• Yokoyama, M., Cho, Y., Aida, R., Reactions of triphosphonitrilic chloride with carboxylic acids, Kgyo Kagaku Zasshi, 66, 609-613, (1963).
• Uslu, A., Balci, C., Yüksel, F., Özcan, E., Dural, S., Beşli, S., The investigation of thermosensitive properties of phosphazene derivatives bearing amino acid ester groups, Journal of Molecular Structure, 1136, 90-99, (2017).