Structural investigation of a new heterocyclic ring system: NMR and X-ray studies

L. Szabó, Gy Kalaus, G. Argay, A. Kálmán, L. Párkányí, P. Kolonits, Cs Szántay

Research output: Contribution to journalArticle

Abstract

The reaction of enamines 4a, b with acrylonitrile gave rise to compounds 6a, b in addition to four (7a-10a and 7b-10b) stereoisomeric derivatives of a new heterocyclic ring system, the structures of which were thoroughly investigated by different spectroscopic methods, in particular by C NMR. Molecular structures of 7a-10a were substantiated by single crystal X-ray diffraction. Crystal data were collected on a CAD-4 diffractometer using monochromatic CuKα radiation (λ = 1.541 80 ̊) and the model structures determined by direct methods were refined on F2 values. The conformations of the four diastereomeric molecules are rather similar. The epimerization at C(12) has only a slight effect on the bond angles around the bridge head atom, while the exchange of the -C2H5 and -C2H4CN functions has practically no impact on the bond lengths, bond angles and torsion angles around C(1). The excellent internal consistency of the molecular geometry permitted characterization of the bond lengths of C(sp3)-X (X = C(sp3), C(aryl), C(sp), etc.) types.

Original languageEnglish
Pages (from-to)249-258
Number of pages10
JournalJournal of Molecular Structure
Volume375
Issue number3
Publication statusPublished - 1996

Fingerprint

Bond length
Nuclear magnetic resonance
X-Rays
Acrylonitrile
X rays
nuclear magnetic resonance
rings
Diffractometers
Model structures
Molecular Structure
X-Ray Diffraction
Torsional stress
Molecular structure
monochromatic radiation
Conformations
Computer aided design
Ion exchange
x rays
acrylonitriles
Head

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics
  • Computational Theory and Mathematics

Cite this

Structural investigation of a new heterocyclic ring system : NMR and X-ray studies. / Szabó, L.; Kalaus, Gy; Argay, G.; Kálmán, A.; Párkányí, L.; Kolonits, P.; Szántay, Cs.

In: Journal of Molecular Structure, Vol. 375, No. 3, 1996, p. 249-258.

Research output: Contribution to journalArticle

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AU - Párkányí, L.

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