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


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.



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

International Standard Serial Number (ISSN)

1528-7483; 1528-7505

Document Type

Article - Journal

Document Version


File Type





© 2003 American Chemical Society (ACS), All rights reserved.

Publication Date

01 May 2003