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Ab Initio and Crystal Structures of (E,E)-1,4-Diphenylbutadiene: A New Type of Arene-Arene Double T-Contact and an Interesting Interlayer Cooperation Involving Diastereoisomeric Contacts
Crystal Growth and Design
  • Rainer Glaser, Missouri University of Science and Technology
  • Laxma R. Dendi
  • Nathan Knotts
  • Charles Leslie Barnes
Abstract

The title compound 1,4-(E,E)-diphenylbutadiene crystallizes in the space group P21/n, and the structure contains three independent molecules A-C with modest twisting about the C-Ph bonds. Each molecule engages in two double face-to-face contacts and in four double T-contacts of a new type. These arene-arene interactions form two-dimensional layers that are stacked in the third dimension. In the new double T-contact, both arenes of each laterally off-set spacer-connected diarene serve as faces or edges in each contact. The occurrence of either one independent molecule (A) in two orientations (+A and -A) or of two independent molecules (B and C) results in two diastereoisomeric double T-contacts in each layer. Molecule A is asymmetric and forms enantiomeric (-A+A) and (-A'+A') layers. The alternation between layers with different pairs of diastereosiomeric double T-contacts allows for reduced surface-matching and better van der Waals interactions between the surfaces of the -A+A (-A'+A') layers and the BC layers.

Department(s)
Chemistry
Keywords and Phrases
  • 1,4 Diphenyl 1,3 Butadiene,
  • Alkene Derivative,
  • Polycyclic Aromatic Hydrocarbon,
  • Unclassified Drug,
  • Ab Initio Calculation,
  • Chemical Bond,
  • Crystal Structure,
  • Crystallization,
  • Diastereoisomer,
  • Molecular Interaction,
  • Molecule,
  • Surface Property
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2003 American Chemical Society (ACS), All rights reserved.
Publication Date
5-1-2003
Publication Date
01 May 2003
Disciplines
Citation Information
Rainer Glaser, Laxma R. Dendi, Nathan Knotts and Charles Leslie Barnes. "Ab Initio and Crystal Structures of (E,E)-1,4-Diphenylbutadiene: A New Type of Arene-Arene Double T-Contact and an Interesting Interlayer Cooperation Involving Diastereoisomeric Contacts" Crystal Growth and Design Vol. 3 Iss. 3 (2003) p. 291 - 300 ISSN: 1528-7483; 1528-7505
Available at: http://works.bepress.com/rainer-glaser/23/