Determination of the tautomeric composition of adenine in the gas phase by vibrational spectroscopy methods: II. Analysis of resonance Raman spectra

Burova, T. G.; Ten, G. N.; Ermolenkov, Vladimir V.; Shcherbakov, R. S.; Lednev, Igor K.

doi:10.1134/s0030400x10120076

Cited by 6 publications

(14 citation statements)

References 12 publications

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“…[3][4][5][6][7][8][9] Fourteen different tautomeric species were found, both for the gas-phase and the aqueous solution, 10 comprising four amino and ten imino forms. In fact, adenine's tautomeric equilibrium has been studied in great detail and at different theoretical levels.…”

Section: Introductionmentioning

confidence: 99%

Applying vibrational spectroscopy to the study of nucleobases – adenine as a case-study

et al. 2013

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A full conformational study of solid-state anhydrous adenine is reported, using vibrational spectroscopy techniques coupled to DFT calculations, for the isolated molecule and the solid. In both cases, the N9H-amino tautomer was found to be the predominant species, followed by the N7H-amino form. An excellent agreement was achieved between experiment and theory, both for wavenumbers and intensities (without the need for scaling). A complete spectral assignment was performed, since all vibrational spectroscopic techniques were available to this study -FTIR, Raman and INS -allowing us to detect and interpret even the lowest frequency vibrational bands, not previously accessed. The quantum mechanical calculations presently carried out represent the highest theoretical level applied so far to the study of nucleobases.

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Section: Introductionmentioning

confidence: 99%

Applying vibrational spectroscopy to the study of nucleobases – adenine as a case-study

et al. 2013

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“…In [5,6], it was suggested that, in this case, Ade N 9 ,N 1 Н + , Ade N 9 Н, Ade N 7 Н, and Ade N 7 ,N 1 Н + are the most probable tautomers. For all four tautomeric forms in the aqueous solution, the vibrational and electronic problems have been previ ously solved [11].…”

Section: Analysis Of Resultsmentioning

confidence: 97%

“…Investigations of the Raman and RRS spectra of adenine in the gas phase [5] show that, along with the prevailing tautomeric form Ade N 9 , the occurrence of which can be considered to be proven, there are also the tautomer Ade N 7 and the imine form Ade N 9 (im). Here, for these three tautomeric forms, we calculated the RHRS spectra in the case of resonances with three long wavelength transitions.…”

Section: Analysis Of Resultsmentioning

confidence: 97%

“…Vibrational and vibronic spectra of nucleic acid bases have been stud ied both theoretically and experimentally [1][2][3][4][5][6][7][8][9]. The results of these studies have made it possible to describe in general the intensity distribution in the spectra and explain their main regular features.…”

Section: Introductionmentioning

confidence: 99%

“…Compara tively recently, to determine the tautomeric composition, Raman scattering, resonant Raman scattering (RRS), and electronic spectroscopy methods have come to be applied. In [5], based on the results of quantum mechan ical calculations of RRS spectra using the method of [10] and the Herzberg-Teller approximation, conclusions on the tautomeric composition of adenine in the gas phase were drawn; in [11], this was done for adenine in an aque ous solution. However, to obtain final conclusions on the tautomeric composition, it is necessary to complement studies of RRS spectra by studies of spectra of other types, in particular, spectra of resonant hyper Raman scattering (RHRS) and two photon absorption.…”

Section: Introductionmentioning

confidence: 99%

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Quantum-mechanical calculations of the intensity distribution in spectra of adenine tautomers: I. Spectra of resonant hyper-Raman scattering

2012

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Ionic and tautomeric conformers of adenine at different pH investigated by Raman spectroscopy combined with DFT calculations

Bhunia

Donfack

Materny

et al. 2016

J Raman Spectroscopy

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Raman spectroscopy and density functional theory studies have been done to determine the ionic and tautomeric conformers of adenine (Ade) in aqueous solution at pH 1.5 (acidic), 7.0 (neutral) and 12.5 (alkaline). The experimental Raman spectra of the aqueous solution of Ade have been recorded for the spectral range of 500-1800 cm À1 . As expected, the recorded Raman spectra of the aqueous solution of Ade at different pH have noticeable differences. The change in the spectral features of Ade at different pH is a result of the change in structure (neutral, cation and anion) of Ade in the aqueous solution. The shifting in the wavenumber position of the Raman bands, along with the change in relative intensity and appearance of new bands with the change of pH, has been explained. In order to determine the structure of Ade at various pH, theoretical Raman spectra, corresponding to the most probable structure of Ade at that particular pH, are calculated by density functional theory-based explicit model. The Raman bands observed at each pH of the aqueous solution of Ade are assigned with the help of a potential energy distribution calculation. The most plausible ionic and neutral conformers of Ade in aqueous solution at pH 1.5, 7.0 and 12.5 are determined by comparing the experimental and theoretical spectra. From this, it is concluded that at neutral pH (7.0), Ade-N9 and Ade-N7 tautomers of Ade predominantly exist along with some signature of imine form of Ade in the aqueous solution. However, single-protonated and double-protonated forms of Ade can exist simultaneously in the aqueous solution at pH 1.5. As per expectation, the anionic form of Ade has been found at alkaline pH (12.5).

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Determination of the tautomeric composition of adenine in the gas phase by vibrational spectroscopy methods: II. Analysis of resonance Raman spectra

Cited by 6 publications

References 12 publications

Applying vibrational spectroscopy to the study of nucleobases – adenine as a case-study

Applying vibrational spectroscopy to the study of nucleobases – adenine as a case-study

Quantum-mechanical calculations of the intensity distribution in spectra of adenine tautomers: I. Spectra of resonant hyper-Raman scattering

Ionic and tautomeric conformers of adenine at different pH investigated by Raman spectroscopy combined with DFT calculations

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