Chem. J. Chinese Universities ›› 1991, Vol. 12 ›› Issue (12): 1627.

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Studies on the 1H NMR Spectra of meso and dl diethyl 2,3-dicyano-2,3-bis(p-substituted phenyl)succinates

Yang Di-lun, Qi Chen-ze, Cui Yu-xin, Dang Hai-shan, Liu You-cheng   

  1. Department of Chemistry, Lanzhou University, Lanzhou, 730000
  • Received:1990-09-04 Online:1991-12-24 Published:1991-12-24

Abstract: The 1H NMR spectra of mesa and dl diethyl 2,3-dicyano-2,3-di(p-Xphenyl)succi-nates(X=OCH3, CH3, H, Cl, NO2) and 1H Noesy spectra of meso and dl isomers of the diethyl ester with X=CH3were determined by using Bruker Am 400 MHz superconducting NMR spectrometry. The corresponding proton of the substituent groups attached to the two central carbon atoms in the molecules are chemical shift equivalence. The average difference between o -1Habsorptions of phenyl in the dl-isomers and that in meso-isomers was found to be △δdl-meso= -120. 1 ± 6.1 Hz. All of the meso-isomers, then, have, methylene (ABX3system) and methyl in the ethoxy at upfield positions, and all of the dl-isorners have that at downfield positions, △δdl-meso= 53. 3 ± 5. 9 Hz and △δdl-meso= 53. 5 ± 5. 4 Hz for Aand Bprotons in the methyienes, and △δdl-meso=39. 3+3. 5 Hz for protons in the methyls. △δdl-meso is the mark of influence of molecular configuration on the chemical shift.

Key words: 1H NMR spectra. Chemical shift, Molecular configuration, Diethyl 2,3-dicyano-2,3-bis(p-substituted phenyDsuccinates

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