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Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism
Author(s) -
Monde Kenji,
Taniguchi Tohru,
Miura Nobuaki,
Vairappan Charles S.,
Suzuki Minoru
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20259
Subject(s) - vibrational circular dichroism , chemistry , circular dichroism , absolute configuration , chirality (physics) , ab initio , density functional theory , computational chemistry , basis set , ab initio quantum chemistry methods , spectral line , stereochemistry , molecule , organic chemistry , physics , chiral symmetry , astronomy , quantum mechanics , nambu–jona lasinio model , quark
Two brominated sesquiterpenes, majapolene B ( 1 ) and acetylmajapolene B ( 2 ), isolated from the red algal genus Laurencia were investigated using vibrational circular dichroism (VCD). The ab initio theoretical VCD and IR calculations of 1 and 2 were performed by density functional theory (DFT) using the B3PW91/6–31G(d,p) basis set. The experimental VCD spectra and corresponding population‐weighted theoretical VCD spectra were found to be in excellent agreement in CCl 4 solution in the 1800–850 cm −1 region, which allowed unambiguous determination of the absolute configurations of (−)‐1 and (−)‐2 as 7 S ,10 S and 7 S ,10 S , respectively. Chirality, 2006. © 2006 Wiley‐Liss, Inc.
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