Synthesis and Structural Determination of a New Chalcone 1,5-Bis(3-Methyl-2-Thienyl)penta-1,4-Dien-3-One, C15h14os2

Contreras, David; Moreno, Yanko; Soto, César; Saavedra, M; Brovelli, Francisco; Baggio, Ricardo

doi:10.4067/s0717-97072009000400032

Cited by 3 publications

(5 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Frontier Molecular Orbitals (FMOs) were used to estimate the most reactive position in the πconjugated system and to describe many forms of reactions [26]. The energy values of the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) and their energy difference (ΔE) represent the molecule's reactivity.…”

Section: Frontier Molecular Orbitalsmentioning

confidence: 99%

Computational determination the reactivity of salbutamol and propranolol drugs

Omer

Koparır²,

Ahmed

et al. 2020

Turkish Computational and Theoretical Chemistry

View full text Add to dashboard Cite

Gaussian software programs 09 was utilized to find the reactivity of salbutamol (SAL) and propranolol (PRO). Density Functional Theory (DFT) and Hartree-Fock (HF) were used to determine the energy band gaps. B3LYP/6-31++G(d,p) lower energy level was chosen as the base set. Geometrical structures with frontier molecular orbitals estimation for both the SAL and PRO. Atomic charge distribution and molecular electrostatic potential evaluation were performed for both drugs. For thermodynamic analysis Ab-initio DFT with HF at 6-31++G base sets were accomplished. The results showed that the PRO is more reactive than SAL.

show abstract

Section: Frontier Molecular Orbitalsmentioning

confidence: 99%

Computational determination the reactivity of salbutamol and propranolol drugs

Omer

Koparır²,

Ahmed

et al. 2020

Turkish Computational and Theoretical Chemistry

View full text Add to dashboard Cite

show abstract

“…The C-C bond length of the cyclohexanone moiety (1.499(5)Å to 1.533(5)Å) are normal single bonds. Similarly, the bond lengths within thiophene rings which include S1 atom are between 1.341 (8)Å and 1.726 (4)Å, which include S2 atom are between 1.378 (6)Å and 1.733(4)Å which exhibit that the rings have the aromatic character [30].…”

Section: X-ray Structure Analysis and Computational Studiesmentioning

confidence: 94%

“…In Table 2, theoretical studies indicated that the shorting of the C=C double bonds (C5=C6, C10=C12) showing the partial double bond character of the C=C bands which are influenced by adjacent conjugated double bonds. Also, the conformation of these molecules is the result of the interaction between the electronic pair of oxygen in the carbonyl group [30].…”

Section: X-ray Structure Analysis and Computational Studiesmentioning

confidence: 99%

“…The electron densities of the frontier molecular orbitals (FMOs) were used for estimating the most reactive position in π-electron systems and to explaine several types of reactions in the conjugated system [30]. The energy values of the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) and their energy gap (ΔE) reflect the chemical reactivity of the molecule.…”

Section: Frontier Molecular Orbitalsmentioning

confidence: 99%

See 1 more Smart Citation

Structural Characterization, Theoretical Investigation and Hirshfeld Surface Analysis of 2,6-(E,E)-bis((thiophene-2-yl)methylene)cyclohexanone

Yakalı¹,

Biçer²,

Cin

2019

Turkish Computational and Theoretical Chemistry

View full text Add to dashboard Cite

The title bis(chalcone) compound has been synthesized and characterized by FTIR, 1H-NMR, 13C-NMR techniques, X-ray structure analysis. The optimized molecular structure of the studied compound is calculated using DFT/B3LYP with 6-31G (d,p) level. The calculated geometrical parameters are in compatible with the experimental data obtained from X-ray structure analysis. The calculated IR fundamental bands, 1H and 13C-NMR chemical shifts of the compound were assigned and compared with the experimental data. Additionally, frontier molecular orbital energies (HOMO, LUMO), their energy gap (∆E), molecular electrostatic potential analysis of the compound have been calculated by the same method. The charge distribution of the molecule is obtained with molecular electrostatic potential (MEP). In addition, the intercontacts in the crystal structure are analyzed using Hirshfeld surfaces computational method. The title compound (C16H14OS2) crystallizes in the monoclinic chiral space group P21/c with a=15.0492(10)Å, b=12.0085(9)Å, c=7.6283(6) Å, β=95.883(7)o, V=1371.31(17)Å3, Dcalc=1.387g/cm3. The central cyclohexanone ring has a chair conformation and the the fragments at the vinyl group of the compound exhibit a trans conformation, and the two thiophene rings adopt a syn conformation and are located on the both side of the cyclohexanone. The asymmetric unit of the title compound, C16H14OS2, contains one-half of a molecule. The other half of the molecule is generated with (x,y,-z) symmetry operator. In the molecule there are two weak C-H…S and C-H…O intramolecular and only C-H…O intermolecular hydrogen bonds. In addition, π…π interactions are found in the crystal structure between the thiophene rings.

show abstract

“…4,6,9 In general there is not much structural information about this class the compounds. The structural information available is related to conformational studies and crystal structure as electronic interactions between oxygen of carbonyl group and the heteroatom 5,7,9 and interatomic interactions of type C-H…O, C-H…p, p…p 10,11 Following our interest in this kind of compounds, mainly directed to their use as potential ligands in further complex development we have synthesized and characterized a new compound in this populous family, viz: ir Spectrum Spectra of 1-(2-thienyl)-3-(3-methyl-2-thienyl)-propenone in KBr pellets were recorded on a FTIR-NICOLET MAGNA 550 spectrometer.…”

Section: 5mentioning

confidence: 99%

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

Moreno

Contreras

Buljan

et al. 2010

J. Chil. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

The new conjugated system ("chalcone kind") reported herein, 1-(2-thienyl)-3-(3-methyl-2-thienyl)-propenone, C 12 H 10 OS 2 presents a monomeric molecular structure, and it most interesting aspects are to be found in it intermolecular interactions, of varied type (C-H···O, C-H···π, π···π) and strength. Some anomalies detected in the refinement process, however, provided evidence that an unexpected in-situ, radiation-induced dimerization reaction had taken place during data collection, with the starting and final products coexisting in a topotactic fashion. This effect is depended of structural packing; that is not all this kind of conjugated system presents this effect. The main factor is the distance between the double bonds of neighboring monomers (about 3 Å)

show abstract

Synthesis and Structural Determination of a New Chalcone 1,5-Bis(3-Methyl-2-Thienyl)penta-1,4-Dien-3-One, C15h14os2

Cited by 3 publications

References 14 publications

Computational determination the reactivity of salbutamol and propranolol drugs

Computational determination the reactivity of salbutamol and propranolol drugs

Structural Characterization, Theoretical Investigation and Hirshfeld Surface Analysis of 2,6-(E,E)-bis((thiophene-2-yl)methylene)cyclohexanone

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

Contact Info

Product

Resources

About