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-CH3-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 []D are the same for both 5 and 6: R(+)/S(−). We conclude that the previously reported AC of 5 is incorrect
Determination of Absolute Configuration Using Ab Initio Calculation of Optical Rotation
BORTOLINI, Olga;
2003
Abstract
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-CH3-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 []D are the same for both 5 and 6: R(+)/S(−). We conclude that the previously reported AC of 5 is incorrectI documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
