Methyl 3-(4-methoxyphenyl)prop-2-enoate

Bujak, Maciej; Zaleski, Jacek; Prezhdo, V. V.; Uspenskiy, Boris

doi:10.1107/s0108270101019539

Cited by 8 publications

(11 citation statements)

References 5 publications

(6 reference statements)

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“…The computed values of above-mentioned angles correlate well with experimental results [13]. The reduction in the angle C 18 -C 20 -O 22 to 111.1…”

Section: Optimized Geometriessupporting

confidence: 83%

“…The evidence of such interaction can be inferred from XRD data [13]. DFT calculation indicates increase of the angles C 1 -C 6 -C 5 and C 1 -C 2 -C 3 by 2.1 • and 1.2…”

Section: Optimized Geometriesmentioning

confidence: 93%

“…The molecules are piled up along the axis to form two parallel plane-to-plane stacks, overlapping to form columns. The angle between molecules form neighbouring [13] stacks is 50.4…”

Section: Second Harmonic Generation Efficiency Measurementsmentioning

confidence: 99%

“…The structure of the title compound, as given by XRD [13], is nearly planar with an average deviation of nonhydrogen atoms from the least squares plane of 0.146Å. The interesting structural features of MMP are the shortening of endocyclic angle C 2 -C 1 -C 6 at the junction of the phenyl ring and propenoate group and increase of the two neighbouring angle around the ring C 1 -C 6 -C 5 and C 1 -C 2 -C 3 resulting from the charge transfer interaction of the phenyl ring and ester group through C 7 =C 18 double bond.…”

Section: Optimized Geometriesmentioning

confidence: 99%

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Intramolecular charge delocalization and nonlinear optical properties of Methyl 3-(4-methoxy phenyl) prop-2-enoate from vibrational spectra

Sajan¹,

Joe²,

Zaleski

et al. 2005

Laser Phys. Lett.

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Abstract:The density functional computations of MMP are performed at B3LYP/6-31G (d,p) level to derive equilibrium geometry, vibrational wavenumbers and intensities, and first hyperpolarizability. Large NLO efficiency predicted for the first time in this new class of compounds has been confirmed by powder efficiency experiments. DFT calculation reveals that endocyclic angle at the junction of the propenoate group and the phenyl ring is decreased from 120• by 2.5• , whereas two neighbouring angles around the ring are increased by 2.1• and 1.2• respectively, associated with intramolecular charge transfer interaction. The vibrational spectra confirm the charge transfer interaction between -COOCH 3 group and phenyl ring through the ethylenic bridge with simultaneous infrared and Raman activation of C7=C18 stretching and ring modes 8 and 19. The large intensity differences observed between 8a and 8b modes in both IR and Raman spectrum due to the algebraic difference of the electronic effects of the substitutents have been discussed. The charge transfer interaction between -COOCH 3 group and phenyl ring through the ethylenic bridge resulting in π-electron cloud movement from donor to acceptor can make the molecule highly polarized and must be responsible for the NLO activity of MMP.

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“…The computed values of above-mentioned angles correlate well with experimental results [13]. The reduction in the angle C 18 -C 20 -O 22 to 111.1…”

Section: Optimized Geometriessupporting

confidence: 83%

“…The evidence of such interaction can be inferred from XRD data [13]. DFT calculation indicates increase of the angles C 1 -C 6 -C 5 and C 1 -C 2 -C 3 by 2.1 • and 1.2…”

Section: Optimized Geometriesmentioning

confidence: 93%

“…The molecules are piled up along the axis to form two parallel plane-to-plane stacks, overlapping to form columns. The angle between molecules form neighbouring [13] stacks is 50.4…”

Section: Second Harmonic Generation Efficiency Measurementsmentioning

confidence: 99%

Section: Optimized Geometriesmentioning

confidence: 99%

See 2 more Smart Citations

Intramolecular charge delocalization and nonlinear optical properties of Methyl 3-(4-methoxy phenyl) prop-2-enoate from vibrational spectra

Sajan¹,

Joe²,

Zaleski

et al. 2005

Laser Phys. Lett.

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show abstract

“…32 Colourless, transparent crystals of MMP were obtained within 2 weeks. Repeated recrystallization yielded good-quality crystals.…”

Section: Experimental Preparationmentioning

confidence: 99%

Vibrational spectral studies of methyl 3-(4-methoxyphenyl)prop-2-enoate, a new organic non-linear optic crystal

Sajan¹,

Binoy²,

Joe³

et al. 2005

J. Raman Spectrosc.

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Single crystals of methyl 3-(4-methoxyphenyl)prop-2-enoate were grown by the slow evaporation technique and vibrational spectral analysis was carried out using near-IR Fourier transform Raman and Fourier transform IR spectroscopy. Ab initio quantum computations were also performed at the HF/6-311G (d,p) level to derive the equilibrium geometry, vibrational wavenumbers and intensities and first hyperpolarizability. The large NLO efficiency predicted for the first time in this new class of compounds was confirmed by powder efficiency experiments. Hartree-Fock calculations reveal that the endocyclic angle at the junction of the propeonate group and the phenyl ring is decreased from 120 • by 2.5 • , whereas the two neighbouring angles around the ring are increased by 2.1 • and 1.2 • , associated with chargetransfer interaction. Vibrational analysis indicates the lowering of asymmetric stretching modes of Me1 and Me2 due to the electronic effects simultaneously caused by back-donation and induction due to the presence of the oxygen atom. The occurrence of Fermi resonance is also identified. The carbonyl stretching vibrations were lowered owing to conjugation and the hydrogen bonding network inside the crystal. The vibrational spectra confirm that the charge-transfer interaction between the -COOCH 3 group and phenyl ring through the ethylenic bridge must be responsible for simultaneous IR and Raman activation of C 7 C 18 stretching and ring modes 8 and 19. The large intensity differences observed between the 8a and 8b modes in both the IR and Raman spectra are due to the algebraic difference of the electronic effects of the substitutents. The charge transfer interaction between the -COOCH 3 group and phenyl ring through the ethylenic bridge resulting in p-electron cloud movement from donor to acceptor can make the molecule highly polarized. Intramolecular charge transfer must be responsible for the NLO activity of MMP.

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Vibrational spectroscopic studies and computational study of methyl(2‐methyl‐4,6–dinitrophenylsulfanyl)ethanoate

Panicker¹,

Raj²,

Varghese

et al. 2010

J Raman Spectroscopy

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FT-IR and FT-Raman spectra of methyl(2-methyl-4,6-dinitrophenylsulfanyl)ethanoate (MDIE) were recorded and analyzed. Surface-enhanced Raman scattering (SERS) spectra were recorded in silver colloid and silver electrode. The vibrational wavenumbers were computed using HF/6-31G * and B3LYP/6-31G * basis. The data obtained from vibrational wavenumber calculations are used to assign vibrational bands obtained in infrared and Raman spectroscopies as well as in SERS of the studied molecule. The first hyperpolarizability and infrared intensities are reported. The geometrical parameters of the title compound are in agreement with the reported similar derivatives. The presence of new bands at 1045 and 948 cm −1 in the SERS spectrum in silver electrode is related to the change in orientation of the molecule with respect to the metal surface. In silver colloid SERS spectrum, the methyl group attached to the methoxy carbonyl group is close to the metal surface, whereas on silver electrode the methyl group attached to the phenyl ring is close to the metal surface.

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Methyl 3-(4-methoxyphenyl)prop-2-enoate

Cited by 8 publications

References 5 publications

Intramolecular charge delocalization and nonlinear optical properties of Methyl 3-(4-methoxy phenyl) prop-2-enoate from vibrational spectra

Intramolecular charge delocalization and nonlinear optical properties of Methyl 3-(4-methoxy phenyl) prop-2-enoate from vibrational spectra

Vibrational spectral studies of methyl 3-(4-methoxyphenyl)prop-2-enoate, a new organic non-linear optic crystal

Vibrational spectroscopic studies and computational study of methyl(2‐methyl‐4,6–dinitrophenylsulfanyl)ethanoate

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