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2-Phenylmalonpiperadide and 2-phenylmalonmorpholide.

Daniel E Lynch1, Gillian E Spicer, Ian McClenaghan

  • 1School of Science and the Environment, Coventry University, Coventry CV1 5FB, England. apx106@coventry.ac.uk

Acta Crystallographica. Section C, Crystal Structure Communications
|December 13, 2003
PubMed
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The crystal structures of two phenylmalonamide derivatives were determined, revealing distinct molecular conformations despite chemical similarities. Both compounds share carbonyl group orientation and chair-like heterocyclic rings, with similar crystal packing due to the same space group.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • 2-phenylmalonpiperadide and 2-phenylmalonmorpholide are chemically similar compounds.
  • Understanding their solid-state structures is crucial for structure-property relationship studies.

Purpose of the Study:

  • To determine and compare the molecular conformations and crystal packing arrangements of 2-phenylmalonpiperadide and 2-phenylmalonmorpholide.
  • To identify similarities and differences in their solid-state structures.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the three-dimensional structures of both compounds.
  • Analysis of molecular conformations and intermolecular interactions, including hydrogen bonding.

Main Results:

Related Experiment Videos

  • The crystal structures of 2-phenylmalonpiperadide (C19H26N2O2) and 2-phenylmalonmorpholide (C17H22N2O4) were elucidated.
  • Despite chemical similarity, the compounds exhibit different molecular conformations.
  • General similarities include carbonyl group orientation, chair conformations of heterocyclic rings, and the same space group (P2(1)2(1)2(1)).
  • Similar packing arrangements and C-H···O hydrogen bonding associations involving carbonyl oxygen atoms were observed.

Conclusions:

  • The study highlights subtle differences in molecular conformation between closely related compounds.
  • Crystal packing is influenced by the specific heterocyclic substituents, despite overall similarities in the molecular backbone and space group.
  • Hydrogen bonding patterns differ, with only one morpholine oxygen participating in such interactions.