Interaction Between Benzene and Naphthalenophane: In the Gas Phase and the Crystalline Lattice

✍ Scribed by Nakamura, Yosuke ;Suzuki, Hideaki ;Hayashida, Yoshitou ;Kudo, Takako ;Nishimura, Jun

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 854 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970821

✦ Synopsis

Abstract

The interaction between naphthalenophane 1 and another aromatic compound in the gas phase was investigated by molecular orbital calculations, mainly focusing on the arrangement of both aromatic compounds and the effect of the substituents in the benzene ring. The X‐ray crystallographic analysis of some clathrates of 1 with an aromatic solvent was also carried out in order to clarify the relationship between the gas and condensed phases. The most stable arrangement calculated for a complex of 1 and benzene or substituted benzene in the gas phase was found to be the arrangement in which the edges of the two naphthalene rings of 1 are directed to the face of the benzene ring. Such an arrangement was also observed in the clathrate crystals, according to the X‐ray crystallographic analysis. This result suggests that the stable arrangement in the gas phase is probably maintained in solution, leading to the same arrangement in the crystals. The order of stabilization of the clathrates with some substituted benzenes is in agreement with that of the electron‐donating ability of the functional group present in the benzene. A slight difference in the stabilization was observed between the complex with toluene and that with chlorobenzene, and such a difference is considered to affect the inclusion behavior of 1.