Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited.
The experimental vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion spectra and corresponding quantum chemical predictions of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol (VANOL) are used to confirm its absolute configuration as (+)(589)-(aR) or (-)(589)-(aS). A discrepancy in the literature crystal structure has been resolved by determining the X-ray crystal structure of the brucine binaphtholphosphate salt of the (aS)-enantiomer of VANOL.
Polavarapu
Prasad L
PL
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA. Prasad.L.Polavarapu@vanderbilt.edu
Petrovic
Ana G
AG
Vick
Sarah E
SE
Wulff
William D
WD
Ren
Hong
H
Ding
Zhensheng
Z
Staples
Richard J
RJ