Chinese Journal of Magnetic Resonance ›› 1990, Vol. 7 ›› Issue (2): 225-230.

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ASSIGNMENT OF THE INDIVIDUAL SHIFTS OF CROWN ETHER DERIVATIVES OF EDTA AND 4'-DANSYLAMINO BENZO CROWN ETHERS' 1H AND 13C NMR SPECTRA

Zhang Anjiang1, Wang Shumei1, Huang Su2, Qing Shenying2   

  1. 1. Cheng du Institute of Organic Chemistry, Academia Sinica;
    2. Department of Chemistry, Sichuan Univtnity, Cheng du
  • Received:1989-05-11 Published:1990-06-05 Online:2018-01-23

Abstract: 1H and 13C NMR spectra of N (,N')-(di) tosyl macro-cyclic ether-bislactones (1-6), N,N'-dicarboxymethyl macrocyclic ether-bislactones and amine-bislactame (8-12) and 4'-dansylamino benzo crown ethers (13-16) etc. eighteen crown ethers were recorded and assigned by consideration of known substitute effects. The 1H chemical shifts obtained indicate that the larger the crown ether, the larger the proton chemical shift for methylene b in Crown 1-6 and for methylene a, b, c in Crown 8-11. These shifts approach a limit when the number of macrocyclic atoms arrives at 21-24. Solvents show considerable effect on the 1H chemical shifts of methylenes a, b, c in Crown 8-11 which increase with the solvent polarity, the order is as follows:CD3COOD > PY-d3 ≥ D2O > CD3OD > CD3CD2OD > DMF-d7 > DMSO-d6.

Key words: Crown ether derivatives of EDTA, NMR