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Enantiomeric recognition of chiral 3,3‐bridged‐1,1′‐binaphthol dimer toward α‐phenylethylamine and α‐amino acid ester
Author(s) -
Liu Tian Jun,
Chen Yong Jun,
Zhang Ke Sheng,
Wang Dong,
Guo Da Wei,
Yang Xiao Zhen
Publication year - 2001
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.1183
Subject(s) - chemistry , enantiomer , dimer , molecule , amine gas treating , titration , stereochemistry , molecular recognition , chiral derivatizing agent , chirality (physics) , chiral column chromatography , organic chemistry , chiral symmetry breaking , nambu–jona lasinio model , physics , quantum mechanics , quark
The 1,1′‐binaphthol‐based dimers with p ‐phenylenebis(2‐ethynyl) spacer, (+)‐ 6 and (+)‐ 2 , were synthesized as chiral host compounds. 1 H NMR, UV‐vis, and fluorescent titration were used to evaluate the enantiomeric recognition abilities of the chiral host dimers toward the guest amine 7 and α‐amino acid ester 8 . The chiral BINOL‐based dimers were found to have good enantiomeric recognition ability. The computer simulation of the host–guest complex molecules was carried out to describe the conformational changes of both naphthyl ring in the molecule of chiral host dimer after complexation with the guest molecule. Chirality 13:595–600, 2001. © 2001 Wiley‐Liss, Inc.