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 - Density functional theory (DFT) calculations
KW - FT-IR and FT-Raman spectra,
KW - Intramolecular hydrogen bonding
KW - Myricetin
KW - Myricitrin
KW - OH stretching frequencies
U2 - 10.1016/j.molstruc.2016.11.069
DO - 10.1016/j.molstruc.2016.11.069
M3 - Journal article
SN - 0166-1280
VL - 1131
SP - 242
EP - 249
JO - Journal of Molecular Structure: THEOCHEM
JF - Journal of Molecular Structure: THEOCHEM
ER -