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

Yıl 2024, Cilt: 24 Sayı: 3, 504 - 518, 27.06.2024

Fehmi Bardak , Etem Kose

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

Öz

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.

Anahtar Kelimeler

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

Proje Numarası

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

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

Öz

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.

Anahtar Kelimeler

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

Destekleyen Kurum

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

Proje Numarası

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

Teşekkür

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.

Kaynakça

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