Analysis of glucopyranoside trinitrate IR spectrum

Korolevich, M. V.; Piottukh-Peletskii, V. N.

doi:10.1007/s10812-008-9013-x

Cited by 3 publications

(8 citation statements)

References 16 publications

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“…On going from unsubstituted monosaccharides to glucopyranosides, the vibrations corresponding to this band retains its shape and strength upon hydroxymethyl substitution of the C (1) hydroxyl [22][23][24][25][26][27]. The calculated spectrum of MTHP that agreed with the experiment indicated that the epoxy group increased the intensity of this band.…”

supporting

confidence: 55%

“…Its frequency increased by ≈20 cm -1 upon methyl-and nitro-substitution in the pyranose ring [23,25]. This was manifested in the experiment by a frequency shift (~20 cm -1 ) of the band corresponding to this vibration at 1260 cm -1 in the spectrum of β-D-glucose on going to methylglucopyranoside [23] and its nitrates [25][26][27]. The calculated spectrum of MTHP showed that the presence of an epoxy group also produceed a high-frequency shift of the ν(OCH) 6 band.…”

mentioning

confidence: 74%

“…The neighboring vibration with ν calc = 1150 cm -1 was localized near C (1) and was a vibration involved mainly with the O (5) -C (1) H-O (1) -C (7) fragment in it. A similar vibration defined as a deformation of the C (1) hydroxymethyl [22,23] occurs in methylglucopyranoside and its nitrates [27]. It forms in spectra of these compounds a high-frequency tail of the complex band in the range 1150-950 cm -1 .…”

mentioning

confidence: 88%

“…This spectral feature has been shown to be persistent if an additional substituent of identical structure and also neighboring substituents of another type are introduced [24]. Additional substitution of the C (1) hydroxyl (4-O-methyl-β-methyl-D-glucopyranoside, 4-O-methyl-β-methyl-D-glucopyranoside nitrates) increases the strength of this band [24,27]. Our results confirmed the previous conclusions about the spectroscopic features of the hydroxymethyl substituents and their characteristics.…”

mentioning

confidence: 99%

“…Unsubstituted monosaccharides are known to have very strong bands in this spectral region that involve C-O-and C-C-stretches and internal deformation vibrations of methylene [30]. Changes connected with the presence of a hydroxymethyl group occur in spectra of methylglucopyranosides and their nitrates [22][23][24]27] as compared with unsubstituted monosaccharides. The structure of the multi-component band at 1150-950 cm -1 became complicated.…”

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confidence: 99%

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Theoretical analysis of the IR spectrum of methyl-3,4-anhydro-α-D-talohexopyranoside

et al. 2008

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A detailed interpretation of the IR spectrum of methyl-3,4-anhydro-α-D-talohexopyranoside that is based on complete calculation of normal vibration frequencies and absolute IR absorption band intensities of the molecule and a comparison of the results obtained with the corresponding experimental data is given for the first time. The influence of the epoxy group on the absorption bands characteristic of the pyranose ring has been analyzed.

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supporting

confidence: 55%

mentioning

confidence: 74%

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confidence: 88%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Theoretical analysis of the IR spectrum of methyl-3,4-anhydro-α-D-talohexopyranoside

et al. 2008

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Calculation of the Structure and IR Spectrum of 2,3-di-O-Nitromethyl-β-D-Glucopyranoside by the Density Functional Method

2015

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The structures of isolated 2,3-di-O-nitromethyl-β-D-glucopyranoside and its H-bonded complexes were modeled using density functional method . Their IR spectra were calculated in the harmonic approximation. It was concluded based on the modeling results that the H-bond affected the structure and IR spectrum of 2,3-di-Onitromethyl-β-D-glucopyranoside. The IR spectrum measured in the range 600-3700 cm -1 at room temperature was interpreted.Introduction. The structure and IR spectrum of isolated methyl-β-D-glucopyranoside and its H-bonded complexes were modeled [1-3] for the fi rst time using the density functional method [4-6], functional B3LYP, and basis set 6-31G(d).The energies were minimized. The geometric, mechanical, and electro-optical parameters and IR frequencies and shapes of normal modes and their intensities were calculated. The interpretation of the experimental IR spectrum of this compound that was proposed earlier [7,8] was refi ned and expanded based on the results. The positive results that were obtained for models outside the bounds of the isolated molecule provided a theoretical basis for analyzing the measured spectra for several glucose derivatives [7-11], e.g., methyl-β-D-glucopyranoside, 2,3-di-O-nitromethyl-β-D-glucopyranoside, 2,6-di-O-nitromethyl-β-D-glucopyranoside, 3,6-di-O-nitromethyl-β-D-glucopyranoside, and 4-O-methyl-2,3,6-di-O-nitromethyl-β-D-glucopyranoside. The previous results [1-3] stimulated analogous studies of the structurally closely related compound 2,3-di-O-nitromethyl-β-D-glucopyranoside and its IR spectrum. The B3LYP/6-31G(d) method [4-6] was used to calculate the energy, geometry, dipole moments, and force constants in the harmonic approximation and the IR spectrum of isolated 2,3-di-O-nitromethyl-β-D-glucopyranoside [12]. The experimental room-temperature IR spectrum of the compound in the range 600-3700 cm -1 was interpreted based on the calculations. The interpretation was preliminary in nature. The presence of a H-bond was indicated by a broad band in the high-frequency IR range that corresponded to hydroxyl stretching modes, the center of gravity of which was shifted to long wavelength by >200 cm -1 relative to its position in the spectrum of the isolated molecule. Consideration of it could enable structural data for the compound to be refi ned and the experimental spectrum to be interpreted. For this, the boundaries of the isolated and quasi-isolated models had to be exceeded, which presupposed calculating the structures and IR spectra of not only the molecule but also its H-bonded complexes. This was a serious independent issue that was resolved using quantum-chemical and spectroscopic methods. The current state of these methods and the algorithms and computing programs gave hope that using them would be successful. Explicit consideration of the H-bond in the modeling reproduced the IR spectrum, which was closer to the experimental one [1][2][3]. This problem as applied to 2,3-di-O-nitromethyl-β-D-glucopyranoside was solved before [13]. Results were obtained for t...

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Modeling of 2,3-di-O-nitro-methyl-β-D-glucopyranoside taking into account the H-bonding using DFT method and interpretation of the IR spectrum of the sample

2014

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Structural-dynamic models of 2,3-di-O-nitro-methyl-β-D-glucopyranoside and its H-complexes have been obtained using density functional method. B3LYP hybrid functional and 6-31G (d) basis have been applied. Energies, structures, dipole moments, polarizabilities, frequencies of normal modes in harmonic approximation and IR intensities have been obtained. IR spectra of the complexes of 2,3-di-O-nitro-methyl-β-D-glucopyranoside and ethanol has been interpreted in 600-3700 cm -1 region. Taking into account the results of simulation we have interpreted IR spectrum of the sample in region 600-3700 cm -1 , and determined the structure of the sample.

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Analysis of glucopyranoside trinitrate IR spectrum

Cited by 3 publications

References 16 publications

Theoretical analysis of the IR spectrum of methyl-3,4-anhydro-α-D-talohexopyranoside

Theoretical analysis of the IR spectrum of methyl-3,4-anhydro-α-D-talohexopyranoside

Calculation of the Structure and IR Spectrum of 2,3-di-O-Nitromethyl-β-D-Glucopyranoside by the Density Functional Method

Modeling of 2,3-di-O-nitro-methyl-β-D-glucopyranoside taking into account the H-bonding using DFT method and interpretation of the IR spectrum of the sample

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