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The Role of Amino Acid Esters and the Amide Group in the Chiral Induction Process by a Novel Monoamide‐Linked Monozinc Bisporphyrinate
Author(s) -
Zhang Yinzhi,
Ma Ben,
Wang Yong,
Hu Chuanjiang
Publication year - 2014
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201400124
Subject(s) - amide , denticity , chemistry , chirality (physics) , amino acid , stereochemistry , hydrogen bond , asymmetric induction , carboxylic acid , peptide bond , molecule , organic chemistry , catalysis , enantioselective synthesis , biochemistry , crystal structure , physics , nambu–jona lasinio model , quark , chiral symmetry breaking , quantum mechanics
A monoamide‐linked monozinc bisporphyrinate for monodentate chiral guests was designed and synthesized. It was used as a host to complex with amino acid esters; the resulting CD spectra showed typical bisignate shape, which suggest the ability to transfer chirality from amino acid esters. The molecular structure of the host indicates that amino acid esters function as monodentate ligands in the host‐guest complex. 1 H NMR spectroscopic studies suggest formation of a hydrogen bond between the amide NH and the carbonyl oxygen groups of the amino acid ester. The possible mechanism of the chiral induction process was further studied by DFT calculations.