Theoretical study of the syn and anti thiophene-2-aldehyde conformers using density functional theory and normal coordinate analysis

Fleming, Guillermo Díaz; Koch, Rainer; Vallete, M.M. Campos

doi:10.1016/j.saa.2006.01.038

Cited by 17 publications

(7 citation statements)

References 18 publications

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“…This assignment is in agreement with the assignments proposed by various authors [20,21]. This mode is well known to mix with neighboring modes (νCC, βCCN/mode no: 43 and βCCC/mode no: 44) as reported in the literature [37].…”

Section: C-s Vibrationssupporting

confidence: 92%

“…The νC-H vibration of the thiophen ring is observed at 3171 cm -1 in FT-IR and 3079 cm -1 in FT-Raman spectra in accordance with the literature [20][21][22]. The harmonic values corresponding to νC-H are calculated in the range 3120-3078 cm -1 (mode nos: 2-4) with TED values >96%.…”

Section: C=c C-c Vibrationssupporting

confidence: 86%

“…The ΓC-H deformation modes are expected to appear in the range 800-1000 cm -1 [32]. , respectively [20][21][22]. For the same mode the computed wavenumbers are: 1508 (C=C), 1490 (C=C) and 1402 cm -1 (C-C).…”

Section: C=c C-c Vibrationsmentioning

confidence: 89%

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FT-IR, FT-Raman and UV-Visible Spectral Analysis on (E)-N′-(thiophen-2-ylmethylene) Nicotinohydrazide

Bharanidharan¹,

Saleem²,

Subashch³

et al. 2017

Arch Chem Res

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Section: C-s Vibrationssupporting

confidence: 92%

Section: C=c C-c Vibrationssupporting

confidence: 86%

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FT-IR, FT-Raman and UV-Visible Spectral Analysis on (E)-N′-(thiophen-2-ylmethylene) Nicotinohydrazide

Bharanidharan¹,

Saleem²,

Subashch³

et al. 2017

Arch Chem Res

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“…Also note that neither thiophene nor thiazole present considerable contributions from their CH bonds, with the sulfur atom dominating the picture. The experimental evidence that shows that 2‐carbonyl substituted thiophenes adopt a preferred intramolecular syn‐conformation, that nucleoside thiazoles display a preference for intramolecular interactions between thiazole sulfur and furanose oxygen, and that short sulfur to carbonyl oxygen distances are observed for oxathiazane and thiazolidine compounds . The nature and directionality of these interactions can be interpreted by the combined use of electrostatic potentials maps and σ* antibonding orbitals.…”

Section: Sid Of Other Nontraditional Hinge Binding Motifsmentioning

confidence: 99%

Quantum mechanical approaches to structurally informed design

Duca¹,

Cross

2013

Int. J. Quantum Chem.

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This review focuses on the application of molecular modeling and structure-informed design (SID) to drug discovery. Routine utilization of quantum mechanical techniques allows generation of SID hypotheses, based on first principles. The authors introduce the concept of combining information from electrostatic potential surfaces and nonbonding orbitals to determine the nature and directionality of intermolecular interactions, particularly those that are infrequently exemplified in the protein data bank.

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“…They found that the syn form of thiophene-2-aldehyde is more stable. Fleming et al [7] studied the syn-and anti-conformers of thiophene-2-aldehyde using density functional method and normal coordinate analysis. They found that the results obtained theoretically are in agreement with experimental statements of the literature.…”

Section: Introductionmentioning

confidence: 99%

First Principle Study of the Anti– and Syn–Conformers of Thiophene–2–Carbonyl Fluoride and Selenophene–2–Carbonyl Fluoride in the Gas and Solution Phases

Abdallah

Ramasami

2009

Lecture Notes in Computer Science

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The anti-and syn-conformers of thiophene-2-carbonyl fluoride (A) and selenophene-2-carbonyl fluoride (B) have been studied in the gas phase. The transition states have also been obtained for the interconversion of the antiand syn-conformers. The methods used are MP2 and DFT/B3LYP and the basis sets used for all atoms are 6-311++G(d,p). The optimized geometries, dipole moments, moment of inertia, energies, energy differences and rotational barriers are reported. This study has been extended to include solvent effect. Some of the vibrational frequencies of the conformers are reported with appropriate assignments. The results indicate that in the gas phase the syn conformer is more stable and the CCSD(T)//MP2 energy differences are 2.97 kJ/mol (A) and 3.02 kJ/mol (B) and barriers of rotation are 38.50 kJ/mol (A) and 36.89 kJ/mol (B). The structures and vibrational frequencies of (A) and (B) are not much affected by the solvents but the more polar conformer gets more stabilized. The major effect of the solvents is that energy difference decreases but rotational barrier increases. The peculiar characteristic of fluorine affecting conformational preference is not observed.

show abstract

Theoretical study of the syn and anti thiophene-2-aldehyde conformers using density functional theory and normal coordinate analysis

Cited by 17 publications

References 18 publications

FT-IR, FT-Raman and UV-Visible Spectral Analysis on (E)-N′-(thiophen-2-ylmethylene) Nicotinohydrazide

FT-IR, FT-Raman and UV-Visible Spectral Analysis on (E)-N′-(thiophen-2-ylmethylene) Nicotinohydrazide

Quantum mechanical approaches to structurally informed design

First Principle Study of the Anti– and Syn–Conformers of Thiophene–2–Carbonyl Fluoride and Selenophene–2–Carbonyl Fluoride in the Gas and Solution Phases

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