Conformational Effect on CNDO Force Field of Furan-2-Aldehyde

Banki, L.; Billes, Ferenc; Gál, M.; Grofcsik, A.; Jalsovszky, G.; Sztraka, L.

doi:10.1016/0022-2860(86)85131-6

Cited by 10 publications

(9 citation statements)

References 7 publications

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“…Microwave data and low-resolution IR data of both molecules have been published [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Those earlier papers reported the rotational and centrifugal constants of the ground state, the molecular structure, and gave a vibrational analysis of band origins and the force field.…”

Section: Introductionmentioning

confidence: 99%

High Resolution IR-Spectra of Furane and Thiophene

Pankoke

Yamada

Winnewisser

1993

Zeitschrift Für Naturforschung A

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University of Gießen. An interactive Loomis-Wood program was applied to identify the c-type transitions of furane and thiophene. The molecular parameters were determined from the observed line positions and the available microwave data by least-squares-fits using Watson's ^-reduced Hamiltonian. Some relations among parameters appearing in different formulations of the Hamiltonian are represented explicitly in connection with the derivation of the unreduced constants. The unreduced constants were derived for both molecules using the planarity relations. We determined the inertial defects to be « 0.05 amuÄ 2 in the ground state and « -0.2 amuÄ 2 in the excited state for both furane and thiophene.

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Section: Introductionmentioning

confidence: 99%

High Resolution IR-Spectra of Furane and Thiophene

Pankoke

Yamada

Winnewisser

1993

Zeitschrift Für Naturforschung A

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“…but assignments were wrong, presumably because of water peaks.7 Comparisons between spectra of the same compound in different media show abundant maxima that are present in one spectrum and absent in others. 33 Theoretical modes are obtained directly from the computer output. Comparison with corresponding calculated modes and experimental results could give a better understanding of such a complex system of bands.…”

Section: Resultsmentioning

confidence: 99%

Theoretical Model of Furan and 2-Furancarboxaldehyde. The Molecular Structure and Vibrational Spectra, Including Isotopic Effects

Montero¹,

González-Jonte²,

Diaz³

et al. 1994

J. Phys. Chem.

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A b initio HF-SCF molecular geometry optimizations and vibrational mode calculations were performed for furan (I) and the two rotational isomers of 2-furancarboxaldehyde (11). Five basis sets were used to compare the quality of results, from minimal M I N I l to large split 6-31G**. The geometry of I agrees fairly well with accurate experimental determinations in the gas phase, and a full accurate theoretical geometry of each isomer of I1 is proposed instead of the incomplete experimental values. Calculated vibrational modes of I agreed with experimental results after appropriate scaling of the calculated harmonic modes. Results of a completevibrational mode analysis for I1 are reported. The effect of isotopic substitution on vibrational energies is fairly well reproduced for I and I1 in comparison with reported experimental results after a new computation of the vibrational energies with the same force constant matrix and different atomic masses. Assignments of bands to different isomers of I1 reopen a discussion about the origin of a carbonyl doublet detected in the liquid phase. Our assignments to C=O stretching bands are based on calculated isotopic displacements, too.

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“…Infrared and Raman spectra of 2-formylfuran were first studied by Allen and Bernstein [ 1 ]. Since then, numbers of experimental and theoretical studies [2][3][4][5][6][7][8][9][10][11][12][13][14][15] have dealt with the infrared, Raman, and microwave spectra of the 2-and 3-subtituted derivatives. Allen and Bernstein [ 1 ] reported that these compounds exist as an equilibrium mixture of two rotational isomers (OO-trans and OO-cis).…”

Section: Introductionmentioning

confidence: 99%

“…Motiyenko et al [ 10 ] reported a microwave spectroscopy study of 2-formylfuran in vibrational excited states and concluded that the cis conformer is less stable than the trans conformer by 286 cm -1 . The effect of conformation on the force field and vibrational spectrum of 2-formylfuran were reported using CNDO/2 force field calculations [ 5 ]. John et al [ 14 ] reported the ab initio molecular calculation for the study of 2-formylfuran, 3-formylfuran, and other related molecules and they found that the cis-trans forms of 3-formylfuran are virtually equi-energetic in the gas phase, while the trans conformer of 2-formylfuran is energetically favored by 3.5 kJ/mol.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, the ability to reliably predict the conformational preference and the rotational barrier is of great interest for systems where the experimental conformational preference is not clear and is strongly solvent dependent. This brief review of the literature shows that 2-formylfuran has received considerable attention both experimental and theoretical [2][3][4][5][6][7][8][9][10][11][12][13]. However, there are very few experimental and theoretical reports about the conformational preference, internal rotation barrier, and vibrational spectral analysis of 3-formylfuran [ 14,15 ] but a detailed quantum chemical computation of the torsional potentials of formylfurans has not been performed.…”

Section: Introductionmentioning

confidence: 99%

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Density Functional Theory Study of the Rotational Barriers, Conformational Preference, and Vibrational Spectra of 2-Formylfuran and 3-Formylfuran

2015

JSC

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The torsional potentials, molecular structures, conformational stability, and vibrational wavenumbers for the rotational isomers of 2-formylfuran and 3-formylfuran are computed using the density functional theory (B3LYP) method with the 6-31+G* basis set. All structures are fully optimized and the optimized geometries, rotational constants, dipole moments, and energies are presented. From the computations, both 2-formylfuran and 3-formylfuran are predicted to exist predominantly in trans conformation with a cis-trans rotational barrier of 11.19 kcal/mol and 8.10 kcal/mol, respectively. The vibrational wavenumbers and the corresponding vibrational assignments of the molecules in the C s symmetry are examined and the infrared spectra of the molecules are simulated using the wavenumbers and the corresponding intensities obtained from the computations. The effect of solvents on the conformational stability of all the molecules in nine different solvents (heptane, chloroform, tetrahydrofuran, dichloroethane, acetone, ethanol, methanol, dimethylsulfoxide, and water) is investigated. The integral equation formalism in the polarizable continuum model (IEF-PCM) is used for all solution phase computations.

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Conformational Effect on CNDO Force Field of Furan-2-Aldehyde

Cited by 10 publications

References 7 publications

High Resolution IR-Spectra of Furane and Thiophene

High Resolution IR-Spectra of Furane and Thiophene

Theoretical Model of Furan and 2-Furancarboxaldehyde. The Molecular Structure and Vibrational Spectra, Including Isotopic Effects

Density Functional Theory Study of the Rotational Barriers, Conformational Preference, and Vibrational Spectra of 2-Formylfuran and 3-Formylfuran

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