The hydrogen bond IR spectra of indole-3-carboxaldehyde and 3-acetylindole crystals – The reason behind their similarity

Flakus, Henryk T.; Hachuła, Barbara; Pyzik, Aleksandra

doi:10.1016/j.chemphys.2010.11.008

Cited by 10 publications

(3 citation statements)

References 39 publications

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“…(b) In other cases of cyclic crystalline systems, e.g., hydrogen-bonded dimers, e.g., arylacetic acids − and styrylacetic acid hydrogen-bonded trimers, e.g., AceOxm , hydrogen-bonded tetramers, e.g., 7-azaindole and 4-methyl-1,2,4-triazole-thione the ν X–H bands are fairly similar to the corresponding spectra of the other group of crystals, i.e., those with open hydrogen-bond chains in their lattices (e.g., crystals diverse amides and thioamides, − 3- and 4-benzaldehyde, indole-3-carboxaldehyde and 3-acetylindole, acetic acid crystals). In this case, the ν X–H band contours can be treated as a “ mirror reflection ” of the corresponding band shapes of systems from point “a”.…”

Section: The Ir Spectra Of Hydrogen-bonded Crystalsmentioning

confidence: 67%

H/D Isotopic and Temperature Effects in the Polarized IR Spectra of Hydrogen-Bond Cyclic Trimers in the Crystal Lattices of Acetone Oxime and 3,5-Dimethylpyrazole

2012

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Polarized IR spectra of hydrogen-bonded acetone oxime and 3,5-dimethylpyrazole crystals were measured at 293 and 77 K in the ν(X-H) and ν(X-D) band frequency ranges. These crystals contain molecular trimers in their lattices. The individual crystal spectral properties remain in a close relation with the electronic structure of the two different molecular systems. We show that a vibronic coupling mechanism involving the hydrogen-bond protons and the electrons on the π-electronic systems in the molecules determines the way in which the vibrational exciton coupling between the hydrogen bonds in the trimers occurs. A strong coupling in 3,5-dimethylpyrazole trimers prefers a "tail-to-head"-type Davydov coupling widespread via the π-electrons. A weak through-space exciton coupling in acetone oxime trimers involves three adjacent hydrogen bonds in each cycle. The relative contribution of each exciton coupling mechanism in the trimer spectra generation is temperature and the molecular electronic structure-dependent. This explains the observed difference in the temperature-induced evolution of the compared spectra. The mechanism of the H/D isotopic "self-organization" processes in the crystal hydrogen bonds was also analyzed. The two types of the hydrogen-bond trimers exhibit the same way, in which the H/D isotopic recognition mechanism occurs. In acetone oxime and 3,5-dimethylpyrazole trimers, identical hydrogen isotope atoms exist in these entire hydrogen-bond systems.

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Section: The Ir Spectra Of Hydrogen-bonded Crystalsmentioning

confidence: 67%

H/D Isotopic and Temperature Effects in the Polarized IR Spectra of Hydrogen-Bond Cyclic Trimers in the Crystal Lattices of Acetone Oxime and 3,5-Dimethylpyrazole

2012

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“…To this group belong crystals of 7-azaindole, 31 4-MeTAS, 21 3-and 4-benzaldehyde, 32 indole-3carboxaldehyde, and 3-acetylindole. 33 A similar property also characterizes spectra of acetic acid crystals. 34 The ν X−H bands in the room-temperature spectra of the hydrogen bond of the tetramer systems from the (a) group are characterized by a relatively low intensity of the higherfrequency branch of each band in comparison with the lowerfrequency band branch intensity.…”

Section: Resultsmentioning

confidence: 82%

“…Crystals formed by molecules with larger π-electronic systems may also exhibit similar spectral properties. To this group belong crystals of 7-azaindole, 4-MeTAS, 3- and 4-benzaldehyde, indole-3-carboxaldehyde, and 3-acetylindole . A similar property also characterizes spectra of acetic acid crystals …”

Section: The “State-of-the-art” In the Research Of Ir Spectra Of Hydr...mentioning

confidence: 83%

Temperature and H/D Isotopic “Self-Organization” Effects in the IR Spectra of the Hydrogen Bond Tetramer Systems in 3,5-Diphenylpyrazole and 4-Methyl-1,2,4-triazolethione Crystals

2012

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Polarized IR spectra of hydrogen-bonded 3,5-diphenylpyrazole and of 4-methyl-1,2,4-triazolethione crystals were measured at 293 and 77 K in the νN-H and νN-D band frequency ranges. These crystals contain molecular tetramers in their lattices. The individual crystal spectral properties remain in close relation with the electronic structure of the two different molecular systems. We show that a vibronic coupling mechanism involving the hydrogen bond protons and the electrons on the π-electronic systems in the molecules determines the way in which the vibrational exciton coupling between the hydrogen bonds in the tetramers occurs. A strong coupling in 3,5-diphenylpyrazole tetramers prefers a "tail-to-head"-type Davydov coupling widespread via the π-electrons. A weak through-space exciton coupling in 4-methyl-1,2,4-triazolethione tetramers involves two opposite hydrogen bonds in the cycles. The relative contributions of each exciton coupling mechanism in the tetramer spectra generation are temperature and the molecular electronic structure dependence. This explains the observed difference in the temperature-induced evolution of the compared spectra. The mechanism of the H/D isotopic ''self-organization'' processes in the crystal hydrogen bonds was also analyzed. The two types of hydrogen bond tetramers differ by the way in which the processes occur. In 3,5-diphenylpyrazole tetramers, identical hydrogen isotope atoms exist in the entire hydrogen bond system, whereas in the case of 4-methyl-1,2,4-triazolethione crystals, the H/D isotopic self-organization mechanism involves the opposite hydrogen bonds in a tetramer.

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Crystal structure, vibrational spectra and DFT studies of hydrogen bonded 1,2,4–triazolium hydrogenselenate

Arjunan

Thirunarayanan

Marchewka

et al. 2017

Journal of Molecular Structure

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The hydrogen bond IR spectra of indole-3-carboxaldehyde and 3-acetylindole crystals – The reason behind their similarity

Cited by 10 publications

References 39 publications

H/D Isotopic and Temperature Effects in the Polarized IR Spectra of Hydrogen-Bond Cyclic Trimers in the Crystal Lattices of Acetone Oxime and 3,5-Dimethylpyrazole

H/D Isotopic and Temperature Effects in the Polarized IR Spectra of Hydrogen-Bond Cyclic Trimers in the Crystal Lattices of Acetone Oxime and 3,5-Dimethylpyrazole

Temperature and H/D Isotopic “Self-Organization” Effects in the IR Spectra of the Hydrogen Bond Tetramer Systems in 3,5-Diphenylpyrazole and 4-Methyl-1,2,4-triazolethione Crystals

Crystal structure, vibrational spectra and DFT studies of hydrogen bonded 1,2,4–triazolium hydrogenselenate

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