Synthesis and GIAO NMR Calculations for Some Novel 4-Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1Hand 13C- Chemical Shifts

Yüksek, Haydar; Čakmak, İsmail; Sadi, S.; Alkan, Muzaffer; Baykara, Haci

doi:10.3390/i6060219

Cited by 36 publications

(20 citation statements)

References 15 publications

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“…Some studies have focused on optimized geometries and conformational distribution [37,38] while others have focused mainly on their NMR properties [39][40][41]. We recently reported the results of a hybrid density functional theory investigation of a series of alloxan-based thiosemicarbazones and semicarbazones [42].…”

Section: 'mentioning

confidence: 99%

“…Theoretical studies can further advance the understanding of the molecular properties of TSC compounds and their complexes with transitional metals, and a few such studies have been recently reported [36][37][38][39][40][41]. Some studies have focused on optimized geometries and conformational distribution [37,38] while others have focused mainly on their NMR properties [39][40][41].…”

Section: 'mentioning

confidence: 99%

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A theoretical investigation on the isomerism and the NMR properties of thiosemicarbazones

Silva

Albu

2007

Open Chemistry

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Hybrid density functional theory calculations at the mPW1PW91/6-31+G(d,p) level of theory have been used to investigate the optimized structures and other molecular properties of five different series of thiosemicarbazones. The investigated compounds were obtained from acenaphthenequinone, isatin and its derivatives, and alloxan. The focus of the study is the isomerism and the NMR characterization of these thiosemicarbazones. It was found that only one isomer is expected for thiosemicarbazones and methylthiosemicarbazones, while for dimethylthiosemicarbazones, two isomers are possible. All investigated thiosemicarbazones exhibit a hydrazinic proton that is highly deshielded and resonates far downfield in the proton NMR spectra. This proton is a part of a characteristic sixmembered ring, and its NMR properties are a result of its strong, intermolecular hydrogen bond. The relationships between the calculated 1 H and 13 C NMR chemical shifts and various geometric parameters are reported.

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Section: 'mentioning

confidence: 99%

Section: 'mentioning

confidence: 99%

A theoretical investigation on the isomerism and the NMR properties of thiosemicarbazones

Silva

Albu

2007

Open Chemistry

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“…Bu yöntemlerden Hatre-Fock (HF) ve Yoğunluk Fonksiyon Teorisi (DFT) literatürdeki birçok çalışmada moleküler özelliklerin etkin ve doğru bir şekilde değerlendirilmesi için kullanılmıştır (Burda et al, 2005;Yüksek et al, 2005a;Yüksek et al, 2005b;Starosta et al, 2010;Shokhmkar et al, 2014;Tamer et al, 2015a;Thanigaimani et al, 2015;Kazici et al, 2016;Preat et al, 2016 …”

Section: Introductionunclassified

2-N-Formilaminotiyofenol Bileşiğinin Spektroskopik Karakterizasyonu, Elektronik ve Çizgisel Olmayan Optik Özellikleri

Akyıldırım¹,

Beytur²,

Kardaş³

et al. 2018

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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ÖZET: Bu çalışmada, 2-N-formilaminotiyofenol bileşiğinin teorik spektroskopik özellikleri incelenerek bazı deneysel verilerle mukayese edilmiştir. Bu amaçla, öncelikle çalışılan bileşik B3LYP, HF yöntemleri ve 6-311G++(d,p) temel seti kullanılarak optimize edilmiştir. Elde edilen optimize yapı yardımıyla GIAO metoduna göre 1 H-NMR ve 13 C-NMR kimyasal kayma değerleri Gaussian G09W programı vasıtasıyla gaz fazında hesaplanmıştır. δ exp=a+b. δ calc. eşitliğine göre teorik değerler ile deneysel veriler SigmaPlot programı kullanılarak grafiğe geçirilmiştir. Elde edilen sonuçlara göre teorik verilerin deneysel verilerle uyumlu oldukları görülmüştür. Çalışmanın teorik kısmında ayrıca, aynı metodlar ve temel set kullanılarak sentezlenen bileşiğin IR frekans değerleri hesaplanmış, bulunan değerler belirli uyum faktörleri ile çarpılmıştır. Teorik infrared spektrumları HF ve B3LYP yöntemlerine göre elde edilmiştir. UV-vis değerleri de etanollü ortamda teorik olarak hesaplanmıştır. İlaveten, molekülün bağ uzunlukları, bağ açıları, Mulliken atomik yükleri, HOMO-LUMO enerjileri, dipol momentleri, toplam enerjileri, iyonlaşma potansiyeli, elektron ilgisi, moleküler yumuşaklık, moleküler sertlik ve elektronegatifliği aynı metodlar ve aynı set kullanılarak hesaplanmıştır. Son olarak, ilgili bileşiğin, çizgisel olmayan optik özellikleri; tek nokta enerji hesabında polar hesapları yapılarak polarizebiliteleri, hiperpolarizebilite değerleri hesaplanmıştır.Anahtar Kelimeler: B3LYP, GIAO, HF, tiyofenol polarizebilite, hiperpolarizebilite ABSTRACT: In this study, the characterization 2-N-formylaminothiophenol has been carried out by quantum chemical method and vibrational spectral techniques. For this purpose, firstly studied compound has been optimized using B3LYP and HF method 6-311G++(d,p) the basic set). The values calculated IR frequencies using the same methods and the basic set of 2-formylaminothiophenol were calculated using Gaussian 09W computer program in gas phase. The founded values are multiplied by appropriate adjustment factors. Theoretical infrared spectrums were obtained according to HF and B3LYP methods. Ved4f program was used for theoretically identification of calculated IR data. Also, 13 C-NMR and 1 H-NMR chemical shift values according to the method GIAO by obtained optimized structure were calculated in DMSO solvent. Theoretically and experimentally obtained values according to exp=a+b. δ calc Eq. were plotted by the SigmaPlot program. In the theoretical part of the study, UVvis values in ethanol were theoretically calculated using Time Dependent-Density Functional Theory (TD-DFT). Additionally, the title compound was found bond angles, bond lengths, the dipole moments, mulliken charges, HOMO-LUMO energy, total energy of the molecule, ionization potential, electron affinity, molecular softness, molecular hardness and electronegativity. Finally, non-linear optical properties of the relevant compound; polarity calculations were made in single point energy calculation, and the polarizability, hyperpolarizability v...

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“…Based on ONIOM2 optimized geometries, the GaugeIncluding Atomic Orbital (GIAO) method as implemented in Gaussian 09 was applied for 1 H NMR calculations [64,65] and by employing B3LYP functional and 6-31G(d) basis set with using corresponding TMS shielding calculated at the same theoretical level as the reference. The solvent effects have been investigated using the PCM method for water as a solvent (ε=78.39).…”

Section: Giao/dft Nmr Studymentioning

confidence: 99%

Inclusion Complex Formation of β-Cyclodextrin with the Nonsteroidal Anti-inflammatory Drug Flufenamic Acid: Computational Study

Belhocine¹,

Bouhadiba²,

Rahim³

et al. 2018

MHC

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Synthesis and GIAO NMR Calculations for Some Novel 4-Heteroarylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives: Comparison of Theoretical and Experimental 1Hand 13C- Chemical Shifts

Cited by 36 publications

References 15 publications

A theoretical investigation on the isomerism and the NMR properties of thiosemicarbazones

A theoretical investigation on the isomerism and the NMR properties of thiosemicarbazones

2-N-Formilaminotiyofenol Bileşiğinin Spektroskopik Karakterizasyonu, Elektronik ve Çizgisel Olmayan Optik Özellikleri

Inclusion Complex Formation of β-Cyclodextrin with the Nonsteroidal Anti-inflammatory Drug Flufenamic Acid: Computational Study

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