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Investigating the Molecular and Spectroscopic Properties of 2-chloroquinoline by Quantum Chemical Computational Methods

Year 2024, , 504 - 518, 27.06.2024

Fehmi Bardak , Etem Kose

https://doi.org/10.35414/akufemubid.1378105

Abstract

The current work deals with the exploration of fundamental molecular properties of 2-chloroquinoline molecule to reveal the chlorine substitution effect on the reactivity and potency of being active matter of quinoline derivatives. Accordingly, it includes a spectroscopic search for 2-chloroquinoline supported by experimental results obtained from FT-IR, FT-Raman, and 1H and 13C NMR spectra, and through quantum chemical calculations. The molecule’s optimized structure and energy parameters were obtained using the density functional theory B3LYP method 6-311++G(d,p) basis set. The vibrational characteristics of the molecule were obtained via the vibrational energy distribution analysis and in accordance with the simulated spectra obtained through molecular modeling. The 1H and 13C NMR chemical shift properties were estimated by the Gauge Invariant Atomic Orbital method and discussed in comparison with the experimental data. Moreover, molecular electrostatic potential surface characteristics, atomic partial charges, electronic orbitals, and possible electronic transitions of the compound were presented. It has been shown that chlorine substitution has significant effects on the fundamental characteristics of the compound and enhances its chemical reactivity in an important manner.

Keywords

2-Chloroquinoline DFT FT-IR Raman UV-Vis NMR

Project Number

FBE-2011/070, FBE-2017/139, ve FBE-2017/148

References

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2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması

Year 2024, , 504 - 518, 27.06.2024

Fehmi Bardak , Etem Kose

https://doi.org/10.35414/akufemubid.1378105

Abstract

Mevcut çalışma, kinolin türevlerinin aktif madde olma potansiyeli ve reaktivitesi üzerindeki klor ikame etkisini ortaya çıkarmak için 2-klorokinolin molekülünün temel moleküler özelliklerinin araştırılmasıyla ilgilidir. Buna göre FT-IR, FT-Raman, 1H ve 13C NMR spektrumlarından elde edilen deneysel sonuçlarla ve kuantum kimyasal hesaplamalarla desteklenen 2-klorokinolin için spektroskopik bir araştırmayı içermektedir. Molekülün optimize edilmiş yapısı ve enerji parametreleri, yoğunluk fonksiyonel teorisi B3LYP yöntemi 6-311++G(d,p) temel seti kullanılarak elde edildi. Molekülün titreşim özellikleri, titreşim enerji dağılımı analizi yoluyla ve moleküler modelleme yoluyla elde edilen simüle edilmiş spektrumlara uygun olarak elde edildi. Atomik Orbitalleri İçeren Gauge Yaklaşımı yöntemiyle tahmin edilen 1H ve 13C NMR kimyasal kayma özellikleri deneysel verilerle karşılaştırıldı. Ayrıca bileşiğin moleküler elektrostatik potansiyel yüzey özellikleri, atomik kısmi yükler, elektronik yörüngeler ve olası elektronik geçişler sunuldu. Klor ikamesinin 2-klorokinolin molekülünün temel özellikleri üzerinde önemli etkileri olduğu ve kimyasal reaktivitesini önemli ölçüde arttırdığı gösterilmiştir.

Keywords

2-klorokinolin DFT FT-IR Raman UV-Vis NMR

Supporting Institution

Manisa Celal Bayar Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi, TÜBİTAK ULAKBİM, Yüksek Performans ve Grid Hesaplama Merkezi

Project Number

FBE-2011/070, FBE-2017/139, ve FBE-2017/148

Thanks

Bu çalışma Manisa Celal Bayar Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi tarafından FBE-2011/070, FBE-2017/139, ve FBE-2017/148 no’lu projelerle desteklenmiştir. Ayrıca yapılan sayısal hesaplamalar tamamen/kısmen TÜBİTAK ULAKBİM, Yüksek Performans ve Grid Hesaplama Merkezi'nde (TRUBA kaynakları) yapılmıştır, desteklerinden dolayı teşekkür ederiz.

References

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  • Arjunan, V., Mohan, S., Balamourougane, P. S., & Ravindran, P. (2009). Quantum chemical and spectroscopic investigations of 5-aminoquinoline. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 74(5), 1215–1223. https://doi.org/10.1016/j.saa.2009.09.039
  • Arjunan, V., Ravindran, P., Rani, T., & Mohan, S. (2011). FTIR, FT-Raman, FT-NMR, ab initio and DFT electronic structure investigation on 8-chloroquinoline and 8-nitroquinoline. Journal of Molecular Structure, 988(1), 91–101. https://doi.org/10.1016/j.molstruc.2010.12.032
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  • Bardak, F., Karaca, C., Bilgili, S., Atac, A., Mavis, T., Asiri, A. M., Karabacak, M., & Kose, E. (2016). Conformational, electronic, and spectroscopic characterization of isophthalic acid (monomer and dimer structures) experimentally and by DFT. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 165, 33–46. https://doi.org/10.1016/j.saa.2016.03.050
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  • Deady, L. W., Desneves, J., Kaye, A., Finlay, G., Baguley, B., & Denny, W. (2001). Positioning of the carboxamide side chain in 11-oxo-11H-indeno[1,2-b]quinolinecarboxamide anticancer agents: Effects on cytotoxicity. Bioorganic and Medicinal Chemistry, 9(2), 445–452. https://doi.org/10.1016/S0968-0896(00)00264-9
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  • Famin, O., Krugliak, M., & Ginsburg, H. (1999). Kinetics of inhibition of glutathione-mediated degradation of ferriprotoporphyrin IX by antimalarial drugs. Biochemical Pharmacology, 58(1), 59–68. https://doi.org/10.1016/S0006-2952(99)00059-3
  • Fort, P. O., Pinto, D. C. G. a, Santos, C. M. M., & Silva, A. M. S. (2007). Advanced NMR techniques for structural characterization of heterocyclic structures. In Recent Research Developments in Heterocyclic Chemistry (Vol. 661, Issue 2).
  • Friebolin, H. (2005). Basic One- and Two-Dimensional NMR Spectroscopy. Wiley. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., … Gaussian 16 Revision A.03 (Gaussian, Inc., Wallingford CT, ). (2016). Gaussian 16 Revision A.03 (A.03). Gaussian, Inc., Wallingford, CT.
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  • Fukui, K. (1982). Role of frontier orbitals in chemical reactions. Science (New York, N.Y.), 218(4574), 747–754. https://doi.org/10.1126/science.218.4574.747
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There are 53 citations in total.

Details

Primary Language Turkish
Subjects Photonics, Optoelectronics and Optical Communications, Atomic, Molecular and Optical Physics (Other)
Journal Section Articles
Authors

Fehmi Bardak 0000-0001-9684-3616

Etem Kose 0000-0001-5791-8873

Project Number FBE-2011/070, FBE-2017/139, ve FBE-2017/148
Early Pub Date June 8, 2024
Publication Date June 27, 2024
Submission Date October 18, 2023
Acceptance Date May 6, 2024
Published in Issue Year 2024

Cite

APA Bardak, F., & Kose, E. (2024). 2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 24(3), 504-518. https://doi.org/10.35414/akufemubid.1378105
AMA Bardak F, Kose E. 2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. June 2024;24(3):504-518. doi:10.35414/akufemubid.1378105
Chicago Bardak, Fehmi, and Etem Kose. “2-Klorokinolinin Moleküler Ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24, no. 3 (June 2024): 504-18. https://doi.org/10.35414/akufemubid.1378105.
EndNote Bardak F, Kose E (June 1, 2024) 2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24 3 504–518.
IEEE F. Bardak and E. Kose, “2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 3, pp. 504–518, 2024, doi: 10.35414/akufemubid.1378105.
ISNAD Bardak, Fehmi - Kose, Etem. “2-Klorokinolinin Moleküler Ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24/3 (June 2024), 504-518. https://doi.org/10.35414/akufemubid.1378105.
JAMA Bardak F, Kose E. 2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24:504–518.
MLA Bardak, Fehmi and Etem Kose. “2-Klorokinolinin Moleküler Ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 3, 2024, pp. 504-18, doi:10.35414/akufemubid.1378105.
Vancouver Bardak F, Kose E. 2-klorokinolinin Moleküler ve Spektroskopik Özelliklerinin Kuantum Kimyasal Hesaplama Yöntemleriyle Araştırılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24(3):504-18.


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