Note

Hydroacridines: Part 23.1H and 13C NMR spectra of sym-octahydroacridine, its 9-(3-pyridyl) and 9-(4-pyridyl) derivatives and the corresponding N(10)-oxides. An experimental approach to the diamagnetic anisotropy of the pyridine nucleus†

  1. Francisc Potmischil1,*,
  2. Călin Deleanu2,
  3. Maria Marinescu1,
  4. Mircea D. Gheorghiu3,‡

Article first published online: 23 JAN 2002

DOI: 10.1002/mrc.996

Issue

Magnetic Resonance in Chemistry

Magnetic Resonance in Chemistry

Volume 40, Issue 3, pages 237–240, March 2002

Additional Information

How to Cite

Potmischil, F., Deleanu, C., Marinescu, M. and Gheorghiu, M. D. (2002), Hydroacridines: Part 23.1H and 13C NMR spectra of sym-octahydroacridine, its 9-(3-pyridyl) and 9-(4-pyridyl) derivatives and the corresponding N(10)-oxides. An experimental approach to the diamagnetic anisotropy of the pyridine nucleus. Magnetic Resonance in Chemistry, 40: 237–240. doi: 10.1002/mrc.996

Author Information

  1. 1

    Department of Organic Chemistry, University of Bucharest, Bulevardul Republicii 13, RO-70031 Bucharest-1, Romania

  2. 2

    National NMR Laboratory, Institute of Organic Chemistry, Splaiul Independentei 202 B, RO-71141 Bucharest-15, Romania

  3. 3

    Department of Organic Chemistry, Politehnica University, Str. Gheorghe Polizu 1, RO-78126 Bucharest-12, Romania

  1. ‡

    Chemistry Department, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

*Department of Organic Chemistry, University of Bucharest, Bulevardul Republicii 13, RO-70031 Bucharest-1, Romania.

  1. †

    For Part 22, see Ref. §.

Publication History

  1. Issue published online: 23 JAN 2002
  2. Article first published online: 23 JAN 2002
  3. Manuscript Accepted: 3 NOV 2001
  4. Manuscript Revised: 29 OCT 2001
  5. Manuscript Received: 31 MAY 2001

Funded by

  • Romanian Ministry of National Education. Grant Number: CNCSU No. 1377/1997.

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Keywords:

  • NMR;
  • 1H NMR;
  • 13C NMR;
  • NOEDIFF NMR;
  • diastereotopy;
  • pyridine;
  • anisotropy effect;
  • ‘ortho-N-oxidation effect’;
  • 1,2,3,4,5,6,7,8-octahydroacridines;
  • aromatic amine oxides;
  • regiospecific N-oxidation

Abstract

The complete 1H NMR chemical shift assignments of 1,2,3,4,5,6,7,8-octahydroacridine (1), 1,2,3,4,5,6,7,8-octahydro-9-(3-pyridyl)acridine (2), 1,2,3,4,5,6,7,8-octahydro-9-(4-pyridyl)acridine (3) and the corresponding N(10)-oxides 1a, 2a and 3a, respectively, were achieved on the basis of 400 MHz 1H NMR spectra and proton–proton decoupling, HMQC and NOEDIFF experiments. The spectral data for the above compounds provided the first experimental evidence of the difference in the anisotropy effect of the two non-symmetrical moieties of the pyridine nucleus, and allowed us to ascertain that the shielding effect of the moiety defined by the C(2′)—N—C(6′) atoms is weaker than that of the C(3′)—C(4′)—C(5′) moiety. The 13C NMR spectra of 1–3 and 1a–3a and the effect of N(10)-oxidation on the 13C NMR chemical shifts are also discussed. The N-oxidation of 2 and 3 with m-chloroperbenzoic acid occurred regiospecifically, affording the N(10)-oxides 2a and 3a free of N(1′)-oxide isomers. Copyright © 2002 John Wiley & Sons, Ltd.

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