Abstract:
:Six enantiomeric pairs of TADDOL-s gathered in two series with either methyl (series A) or phenyl (series B) substituent in 2-position of the dioxolane ring were studied by vibrational circular dichroism (VCD). Experimental IR and VCD spectra associated with density functional theory (DFT) calculations showed that the two series exhibit quite different conformations in solution. In series A, the conformer with anti C-O bonds and stabilized by intramolecular OH...OH hydrogen bonding prevails, whereas in series B the conformer with gauche C-O bonds and intramolecular OH...π hydrogen bonding is favored. The shape and sign of the VCD bands in the O-H stretching region revealing the nature of the intramolecular hydrogen bonding were clearly identified. Polarimetric measurements showed that, within the same absolute configuration, compounds in series A and in series B have opposite signs of optical rotation.
journal_name
Chiralityjournal_title
Chiralityauthors
Uncuta C,Bartha E,Gherase D,Teodorescu F,Draghici C,Cavagnat D,Daugey N,Liotard D,Buffeteau Tdoi
10.1002/chir.20829subject
Has Abstractpub_date
2010-01-01 00:00:00pages
E115-22eissn
0899-0042issn
1520-636Xjournal_volume
22 Suppl 1pub_type
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