INTERACTION BETWEEN BENZENE AND NAPHTHALENOPHANE - IN THE GAS-PHASE AND THE CRYSTALLINE LATTICE

Citation
Y. Nakamura et al., INTERACTION BETWEEN BENZENE AND NAPHTHALENOPHANE - IN THE GAS-PHASE AND THE CRYSTALLINE LATTICE, Liebigs Annalen, (8), 1997, pp. 1769-1776
Citations number
18
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
ISSN journal
0947-3440
Issue
8
Year of publication
1997
Pages
1769 - 1776
Database
ISI
SICI code
0947-3440(1997):8<1769:IBBAN->2.0.ZU;2-J
Abstract
The interaction between naphthalenophane 1 and another aromatic compou nd in the gas phase was investigated by molecular orbital calculations , mainly focusing on the arrangement of both aromatic compounds and th e effect oi the substituents in the benzene ring. The X-ray crystallog raphic analysis of some clathrates of 1 with an aromatic solvent was a lso carried out in order to clarify the relationship between the gas a nd condensed phases. The most stable arrangement calculated for a comp lex 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 arrangemen t was also observed in the clathrate crystals, according to the X-ray crystallographic analysis. This result suggests that the stable arrang ement in the gas phase is probably maintained in solution, leading to the same arrangement in the crystals. The order of stabilization of th e clathrates with some substituted benzenes is in agreement with that of the electron-donating ability of the functional group present in th e benzene. A slight difference in the stabilization was observed betwe en the complex with toluene and that with chlorobenzene, and such a di fference is considered to affect the inclusion behavior of 1.