Intramolecular hydrogen bonding in myricetin and myricitrin

Quantum chemical calculations and vibrational spectroscopy

Danijela Vojta, Katarina Dominkovic, Snezana Miljanic, Jens Spanget-Larsen

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

The molecular structures of myricetin (3,3’,4’,5,5’,7-hexahydroxyflavone; MCE) and myricitrin (myricetin 3-O-rhamnoside; MCI) are investigated by quantum chemical calculations (B3LYP/6-311G**). Two preferred molecular rotamers of MCI are predicted, corresponding to different conformations of the O-rhamnoside subunit. The rotamers are characterized by different hydrogen bonded cross-links between the hydroxy groups of the rhamnoside substituent and the parent MCE moiety. The predicted OH stretching frequencies are compared with vibrational spectra of MCE and MCI recorded for the sake of this investigation (IR and Raman). In addition, a reassignment of the C=O stretching bands are suggested.
OriginalsprogEngelsk
TidsskriftJournal of Molecular Structure: THEOCHEM
Vol/bind1131
Sider (fra-til)242-249
Antal sider8
ISSN0166-1280
DOI
StatusUdgivet - 5 mar. 2017

Citer dette

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title = "Intramolecular hydrogen bonding in myricetin and myricitrin: Quantum chemical calculations and vibrational spectroscopy",
abstract = "The molecular structures of myricetin (3,3’,4’,5,5’,7-hexahydroxyflavone; MCE) and myricitrin (myricetin 3-O-rhamnoside; MCI) are investigated by quantum chemical calculations (B3LYP/6-311G**). Two preferred molecular rotamers of MCI are predicted, corresponding to different conformations of the O-rhamnoside subunit. The rotamers are characterized by different hydrogen bonded cross-links between the hydroxy groups of the rhamnoside substituent and the parent MCE moiety. The predicted OH stretching frequencies are compared with vibrational spectra of MCE and MCI recorded for the sake of this investigation (IR and Raman). In addition, a reassignment of the C=O stretching bands are suggested.",
keywords = "Myricetin, Myricitrin, Density functional theory (DFT) calculations, FT-IR and FT-Raman spectra,, OH stretching frequencies, Intramolecular hydrogen bonding",
author = "Danijela Vojta and Katarina Dominkovic and Snezana Miljanic and Jens Spanget-Larsen",
year = "2017",
month = "3",
day = "5",
doi = "10.1016/j.molstruc.2016.11.069",
language = "English",
volume = "1131",
pages = "242--249",
journal = "Journal of Molecular Structure: THEOCHEM",
issn = "0166-1280",
publisher = "Elsevier BV",

}

Intramolecular hydrogen bonding in myricetin and myricitrin : Quantum chemical calculations and vibrational spectroscopy. / Vojta, Danijela; Dominkovic, Katarina; Miljanic, Snezana; Spanget-Larsen, Jens.

I: Journal of Molecular Structure: THEOCHEM, Bind 1131, 05.03.2017, s. 242-249.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Intramolecular hydrogen bonding in myricetin and myricitrin

T2 - Quantum chemical calculations and vibrational spectroscopy

AU - Vojta, Danijela

AU - Dominkovic, Katarina

AU - Miljanic, Snezana

AU - Spanget-Larsen, Jens

PY - 2017/3/5

Y1 - 2017/3/5

N2 - The molecular structures of myricetin (3,3’,4’,5,5’,7-hexahydroxyflavone; MCE) and myricitrin (myricetin 3-O-rhamnoside; MCI) are investigated by quantum chemical calculations (B3LYP/6-311G**). Two preferred molecular rotamers of MCI are predicted, corresponding to different conformations of the O-rhamnoside subunit. The rotamers are characterized by different hydrogen bonded cross-links between the hydroxy groups of the rhamnoside substituent and the parent MCE moiety. The predicted OH stretching frequencies are compared with vibrational spectra of MCE and MCI recorded for the sake of this investigation (IR and Raman). In addition, a reassignment of the C=O stretching bands are suggested.

AB - The molecular structures of myricetin (3,3’,4’,5,5’,7-hexahydroxyflavone; MCE) and myricitrin (myricetin 3-O-rhamnoside; MCI) are investigated by quantum chemical calculations (B3LYP/6-311G**). Two preferred molecular rotamers of MCI are predicted, corresponding to different conformations of the O-rhamnoside subunit. The rotamers are characterized by different hydrogen bonded cross-links between the hydroxy groups of the rhamnoside substituent and the parent MCE moiety. The predicted OH stretching frequencies are compared with vibrational spectra of MCE and MCI recorded for the sake of this investigation (IR and Raman). In addition, a reassignment of the C=O stretching bands are suggested.

KW - Myricetin

KW - Myricitrin

KW - Density functional theory (DFT) calculations

KW - FT-IR and FT-Raman spectra,

KW - OH stretching frequencies

KW - Intramolecular hydrogen bonding

U2 - 10.1016/j.molstruc.2016.11.069

DO - 10.1016/j.molstruc.2016.11.069

M3 - Journal article

VL - 1131

SP - 242

EP - 249

JO - Journal of Molecular Structure: THEOCHEM

JF - Journal of Molecular Structure: THEOCHEM

SN - 0166-1280

ER -