Original scientific paper

Deuterium Isotope Effects in 13C NMR Spectra of trans-N-Salicylideneaniline Isotopomers

Viliko Smrečki orcid.org/0000-0002-0461-5542 ; Ruđer Bošković Institute, Department of Organic Chemistry and Biochemistry, P. O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Predrag Novak ; Ruđer Bošković Institute, Department of Organic Chemistry and Biochemistry, P. O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Dražen Vikić-Topić ; Ruđer Bošković Institute, Department of Organic Chemistry and Biochemistry, P. O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Tomica Hrenar ; Laboratory of Analytical Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Strossmayerov trg 4, HR-10000 Zagreb, Croatia
Zlatko Meić ; Laboratory of Analytical Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Strossmayerov trg 4, HR-10000 Zagreb, Croatia

Abstract

A series of isotopically labelled trans-N-salicylideneaniline (SAN) isotopomers has been prepared (2'-2H-, 3'-2H-, 4'-2Hand 2',3',4',5',6-2H5-SAN) and their 13C NMR spectra recorded and analyzed. Deuterium isotope effects (DIEs) in 13C NMR spectra of SAN isotopomers have been compared with those observed in the corresponding isotopomers of related binuclear aromatic molecules. Most of DIEs in SAN resemble those previously reported for similar molecular systems, except for some effects over three bonds. It is suggested that the participation of SAN nitrogen Ione pair in the intramolecular hydrogen bond is responsible for the observed difference in DIEs through three bonds at the aniline ring ortho carbon.

Keywords

NMR; XH; 13C; deuterium isotope effects; salicylidene-aniline; hydrogen bond

Hrčak ID:

127483

URI

https://hrcak.srce.hr/127483

Publication date:

4.2.2002.

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