Stabilization of a high energy molecular conformation by specific intermolecular forces, a novel planar benzylideneaniline system

Oshrit Navon, Joel Bernstein

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The system containing six benzylideneanilines (BA) has been studied: Group 1: I: N-(p-Chlorobenzylideneaniline)m-chloroaniline (BA, X = 4 - Cl, Y = 3 - Cl) II: N-(p-Bromobenzylideneaniline)m-bromoaniline (BA, X = 4 - Br, Y = 3 - Br) III: N-(p-Bromobenzylideneaniline)m-chloroaniline (BA, X = 4 - Br, Y = 3 - Cl) IV: N-(p-Chlorobenzylideneaniline)m-bromoaniline (BA, X = 4 - Cl, Y = 3 - Br) Group 2: V: N-(m-Chlorobenzylideneaniline)p-bromoaniline (BA, X = 3 - Cl, Y = 4 - Br) VI: N-(m-Bromobenzylideneaniline)p-chloroaniline (BA, X = 3 - Br, Y = 4 - Br) The crystal structures of Group 1 are isostructural. They crystallize in a monoclinic cell, space group P2l. They are rare examples of planar benzylideneanilines in a nondisordered crystal structure. The crystal structures exhibit an intermolecular ring containing five atoms and hal - hal, C - H - hal interactions, which may contribute to the planarity of the molecule. The structures in Group 2 crystallize in a monoclinic cell, space group P2l/c. The conformation is nonplanar and there are no intermolecular halogen - halogen interactions. The abovementioned live atom pattern ring does not occur in these structures. These two groups of structures show that the type and mode of molecular substitution can lead to specific intermolecular interactions which in turn stabilize an otherwise unfavorable molecular conformation.

Original languageEnglish
Pages (from-to)3-11
Number of pages9
JournalStructural Chemistry
Volume8
Issue number1
DOIs
StatePublished - 1 Jan 1997

Keywords

  • Benzylideneaniline
  • Intermolecular forces
  • Molecular conformation

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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