Year 2020, Volume 10 , Issue 1, Pages 386 - 398 2020-03-01

Synthesis and Characterization of Squaramic Acid Derivatives of 4-(Hetarilazoil)anilines
4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu

Fatih EYDURAN [1] , Mine AYDOĞAN YERLİKAYA [2]


In the study, synthesis of squaramic acids having azo group (compounds 4-6) were carried out in a one-pot. For the synthesis of compounds 4-6, firstly azo dyes bearing the free amine group (compounds 1-3) were obtained by the diazo-coupling method. In this method, the starting compound 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione was obtained in the methanol medium as a result of the single substitution of methanol with squaric acid and used in the synthesis of compounds 4-6 without isolation. Compounds 4-6 were synthesized in a one-pot in a low yield in methanol medium as a result of single displacement reaction between compounds 1-3 and 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione. Chemical structures of compounds 2, 4, 5, 6 were confirmed by spectroscopic methods (FTIR, NMR). In addition, UV-Vis absorption spectra of compounds 4-6 in different solutions were taken and evaluated. In this synthesis method, it was determined that compound 1 and 2 were selectively substituted with the -OCH3 group of 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione compared -OH group.

Çalışmada, azo grubu taşıyan skuaramik asitlerin (bileşikler 4-6) sentezleri tek-kap içerisinde gerçekleştirildi. Bileşikler 4-6’nın sentezi için önce serbest amino grubu içeren azo boyarmaddeleri (bileşikler 1-3), diazo-kenetlenme yöntemiyle elde edildi. Bu yöntemde, çıkış bileşiği 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion, metanol ortamında, metanolün skuarik asit ile tekli yerdeğiştirmesi sonucunda elde edilmiş ve izole edilmeden bileşikler 4-6’nın sentezinde kullanılmıştır. Bileşikler 4-6, elde edilen bileşikler 1-3’ün 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion arasındaki tekli yerdeğiştirme tepkimesi sonucunda tek-kap içerisinde metanol ortamında düşük verimlerle sentezlenmiştir. Bileşikler 2, 4, 5 ve 6’nın kimyasal yapıları, spektroskopik yöntemler (FTIR, NMR) ile aydınlatılmıştır. Ayrıca, farklı çözelti ortamlarında bileşikler 4-6’nın UV-Görünür bölge absorpsiyon spektrumları alınmış ve değerlendirilmiştir. Bu sentez yönteminde, bileşikler 1-3, 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion’un -OCH3 grubu ile -OH grubuna göre bişelik 3 hariç seçimli yer değiştirdiği belirlenmiştir.

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Primary Language tr
Subjects Engineering, Chemical
Published Date Mart-2020
Journal Section Kimya / Chemistry, Kimya Mühendisliği / Chemical Engineering
Authors

Orcid: 0000-0003-0488-3691
Author: Fatih EYDURAN (Primary Author)
Institution: ADNAN MENDERES ÜNİVERSİTESİ
Country: Turkey


Orcid: 0000-0001-8016-490X
Author: Mine AYDOĞAN YERLİKAYA
Institution: ADNAN MENDERES ÜNİVERSİTESİ
Country: Turkey


Dates

Application Date : March 20, 2019
Acceptance Date : October 7, 2019
Publication Date : March 1, 2020

Bibtex @research article { jist542445, journal = {Journal of the Institute of Science and Technology}, issn = {2146-0574}, eissn = {2536-4618}, address = {}, publisher = {Igdir University}, year = {2020}, volume = {10}, pages = {386 - 398}, doi = {10.21597/jist.542445}, title = {4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu}, key = {cite}, author = {EYDURAN, Fatih and AYDOĞAN YERLİKAYA, Mine} }
APA EYDURAN, F , AYDOĞAN YERLİKAYA, M . (2020). 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology , 10 (1) , 386-398 . DOI: 10.21597/jist.542445
MLA EYDURAN, F , AYDOĞAN YERLİKAYA, M . "4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu". Journal of the Institute of Science and Technology 10 (2020 ): 386-398 <https://dergipark.org.tr/en/pub/jist/issue/52503/542445>
Chicago EYDURAN, F , AYDOĞAN YERLİKAYA, M . "4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu". Journal of the Institute of Science and Technology 10 (2020 ): 386-398
RIS TY - JOUR T1 - 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu AU - Fatih EYDURAN , Mine AYDOĞAN YERLİKAYA Y1 - 2020 PY - 2020 N1 - doi: 10.21597/jist.542445 DO - 10.21597/jist.542445 T2 - Journal of the Institute of Science and Technology JF - Journal JO - JOR SP - 386 EP - 398 VL - 10 IS - 1 SN - 2146-0574-2536-4618 M3 - doi: 10.21597/jist.542445 UR - https://doi.org/10.21597/jist.542445 Y2 - 2019 ER -
EndNote %0 Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu %A Fatih EYDURAN , Mine AYDOĞAN YERLİKAYA %T 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu %D 2020 %J Journal of the Institute of Science and Technology %P 2146-0574-2536-4618 %V 10 %N 1 %R doi: 10.21597/jist.542445 %U 10.21597/jist.542445
ISNAD EYDURAN, Fatih , AYDOĞAN YERLİKAYA, Mine . "4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu". Journal of the Institute of Science and Technology 10 / 1 (March 2020): 386-398 . https://doi.org/10.21597/jist.542445
AMA EYDURAN F , AYDOĞAN YERLİKAYA M . 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu. Iğdır Üniv. Fen Bil Enst. Der.. 2020; 10(1): 386-398.
Vancouver EYDURAN F , AYDOĞAN YERLİKAYA M . 4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu. Journal of the Institute of Science and Technology. 2020; 10(1): 398-386.