Conformational equilibria of TADDOL-s in solution investigated by vibrational circular dichroism.

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

Chirality

journal_title

Chirality

authors

Uncuta C,Bartha E,Gherase D,Teodorescu F,Draghici C,Cavagnat D,Daugey N,Liotard D,Buffeteau T

doi

10.1002/chir.20829

subject

Has Abstract

pub_date

2010-01-01 00:00:00

pages

E115-22

eissn

0899-0042

issn

1520-636X

journal_volume

22 Suppl 1

pub_type

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