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Determination of absolute configuration using ab initio calculation of optical rotation
Author(s) -
Stephens P.J.,
Devlin F.J.,
Cheeseman J.R.,
Frisch M.J.,
Bortolini O.,
Besse P.
Publication year - 2003
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.10270
Subject(s) - chemistry , absolute configuration , ab initio , thiophene , ab initio quantum chemistry methods , optical rotation , density functional theory , computational chemistry , oxide , specific rotation , stereochemistry , organic chemistry , molecule
Ab initio Density Functional Theory (DFT) calculations of transparent spectral region, discrete frequency specific rotations were used to assign the absolute configurations (ACs) of: 1, 2H‐naphtho[1,8‐bc]thiophene 1‐oxide; 2, m‐F‐phenyl glycidic acid methyl ester; 3, o‐Br‐phenyl glycidic acid methyl ester; 4, p‐CH 3 ‐phenyl glycidic acid methyl ester; 5, 2‐(1‐hydroxyethyl)‐chromen‐4‐one; and 6, 6‐Br‐2‐(1‐hydroxyethyl)‐chromen‐4‐one. The ACs of 5 and 6 were previously determined via X‐ray crystallography to be: 5, R(−)/S(+); 6, R(+)/S(−). The ACs obtained using [α] D are the same for both 5 and 6: R(+)/S(−). We conclude that the previously reported AC of 5 is incorrect. Chirality 15:S57–S64, 2003. © 2003 Wiley‐Liss, Inc.
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