A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy

Asadi, Zahra; Esrafili, Mehdi D.; Vessally, Esmail; Asnaashariisfahani, Manzarbanou; Yahyaei, Saeideh; Khani, Ali

doi:10.1016/j.molstruc.2016.09.027

Cited by 42 publications

(22 citation statements)

References 27 publications

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“…The optimized tube structures are shown in Figure . Calculated bond distances and bond angles are in good agreement with a very recent high‐level calculation made at the B3LYP/6‐311++G(d,p) DFT level (bond distances in this work are around 0.01 Å higher and bond angles agree within a few degrees) . The higher level calculation was found to display structural parameters close to experimental values.…”

Section: Resultssupporting

confidence: 87%

“…The dipole moment calculated in this work has a value of 3.28 Debye compared to the reported value of 3.2 Debye, and is similarly oriented perpendicular with respect to the piperdine ring. The optimized structures of the two species as shown in Figure are very similar with all their functional groups oriented in analogous directions, the main chemical difference being the C ** ‐carboxylic group in carfentanil. The study of Asadi et al did not include experimental NR or DFT Raman, both of which we report in the next section …”

Section: Resultsmentioning

confidence: 80%

“…, but its origin was not investigated . It is also absent from experimental and computational IR‐spectra of fentanyl, and it cannot be assigned at this time …”

Section: Discussionmentioning

confidence: 99%

“…Fentanyl was studied on both gold and silver with FT‐Raman spectroscopy, but that study focused on cocaine and other illicit drugs and presented no spectral data for fentanyl. Another work has investigated the use of density functional theory (DFT) calculations for comparing NMR and IR spectroscopic data . There still is a need for a nondestructive, sensitive, and rapid method that combines experimental and theoretical data to provide precise and invaluable information.…”

Section: Introductionmentioning

confidence: 99%

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SERS, Raman, and DFT analyses of fentanyl and carfentanil: Toward detection of trace samples

Leonard

Haddad

Green³

et al. 2017

J Raman Spectroscopy

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We examine the normal Raman and the surface‐enhanced Raman spectra of fentanyl and carfentanil. As an aid in the assignment of the spectral lines, we present a density functional theory calculation. Although Raman spectroscopy is a valuable analytic tool for the detection and identification of molecular species, it is a weak effect and requires specialized equipment for detection of trace samples. We therefore turn to surface‐enhanced Raman spectroscopy, which utilizes the large enhancement of the Raman signal endowed by proximity to silver or gold nanoparticles. The enhancement factor (EF) obtained in this experiment is ≥1.6 × 105. This points the way towards future development of a simple and sensitive technique for the detection of analytes in trace quantities, particularly for wider application in forensic science.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 80%

“…, but its origin was not investigated . It is also absent from experimental and computational IR‐spectra of fentanyl, and it cannot be assigned at this time …”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

SERS, Raman, and DFT analyses of fentanyl and carfentanil: Toward detection of trace samples

Leonard

Haddad

Green³

et al. 2017

J Raman Spectroscopy

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“…HOMO and LUMO energy band gap is an important factor in determination of molecular electrical properties [44]. HOMO indicates the electron-donating capability and LUMO presents the electron accepting capability of a molecule [45].…”

Section: Homo-lumo Analysesmentioning

confidence: 99%

Experimental and Theoretical Investigations of Molecular Structure and Vibrational Frequencies of Hypericin Molecule

Özdemir¹,

Gökçe²

2017

Cumhuriyet Science Journal

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In the present study, vibrational analysis of hypericin molecule was experimentally performed using FT-IR spectroscopy. The molecular structure, geometric parameters, vibrational wavenumbers, molecular electrostatic potential and the highest and the lowest occupied molecular orbital analyses of hypericin molecule were theoretically obtained with Density Functional Theory. The vibrational wavenumbers were consistent with literature and the experimental data obtained in the current study.

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Facile Synthesis of the Shape‐Persistent 4‐Hydroxybenzaldehyde Based Macrocycles and Exploration of their Key Electronic Properties: An Experimental and DFT Approach

et al. 2022

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In the current study, a series of stabilized bis-acetylene incorporated 4-hydroxybenzaldehyde based macrocycles using the alkyne-homocoupling approach were synthesized in moderate yields. A total of six newly stiff macrocycles were synthesized in a stepwise manner starting from 4-hydroxybenzaldehyde. In the first step, base mediated propargylation was performed followed by copper mediated terminal alkyne homocoupling. The alkyne homocoupled substrate having carbonyl at both the terminals is cyclized in the final step via double imine formation reactions using substituted diamines as linker. All the newly synthesized rigid framework of the macrocycles were optimized at B3LYP/6-31G (d,p) level of theory. Nonlinear optical behaviors of the synthesized macrocycles were explored by the DFT calculations where high values of first-order hyperpolarizability and dipole moment were examined. In the reported study, a good agreement between experimental and theoretical parameters was observed that may play a significant contribution for the NLO applications.

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A structural study of fentanyl by DFT calculations, NMR and IR spectroscopy

Cited by 42 publications

References 27 publications

SERS, Raman, and DFT analyses of fentanyl and carfentanil: Toward detection of trace samples

SERS, Raman, and DFT analyses of fentanyl and carfentanil: Toward detection of trace samples

Experimental and Theoretical Investigations of Molecular Structure and Vibrational Frequencies of Hypericin Molecule

Facile Synthesis of the Shape‐Persistent 4‐Hydroxybenzaldehyde Based Macrocycles and Exploration of their Key Electronic Properties: An Experimental and DFT Approach

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