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Chiral exploration of 6,12‐diphenyldibenzo[ b , f ][1,5]diazocine with stable conformation
Author(s) -
Li ZhengYi,
Pan Yong,
Jin LinLin,
Yin Yue,
Yang BaoZhu,
Sun XiaoQiang
Publication year - 2017
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.22680
Subject(s) - chemistry , enantiomer , optical rotation , circular dichroism , absolute configuration , chirality (physics) , resolution (logic) , crystallography , density functional theory , crystal structure , stereochemistry , computational chemistry , chiral symmetry , organic chemistry , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
A first optical resolution of 6,12‐diphenyldibenzo[ b , f ][1,5]diazocine with stable boat conformation was achieved by chiral supercritical fluid chromatography (SFC). The absolute configurations of enantiomers were first assigned and determined by X‐ray crystal structure based on CIP‐rules. The high optical rotation and circular dichroism spectrum were well explained by electronic helix theory. Owing to the high stabilization of boat conformation, the chiral configuration could be maintained at very high temperature, more than 200 °C, which was proved by Density Functional Theory calculations.