Res. Chem. Intermed.
, Vol. 27, No. 9, pp. 911–916 (2001)
A quantum chemistry study on the structure and
properties of a novel stable strained cyclophane
RONG CHEN, KE-CHUN ZHANG, LEI LIU and QING-XIANG GUO
Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China
Received 22 November 2000; accepted 2 May 2001
Abstract—Different levels of theoretical methods have been used to study a novel stable cylcophane
,4-biphenyldiyl)]naphthalene. It was concluded that HF /3-21g
the most ef cient method for the system, which could well reproduce the experimental structure.
In addition, HF /3-21g
calculations explained the experimental observation that
the cyclophane was much easier to be oxidized to the corresponding radical cation than its related
compound 1,8-bisphenyl-naphthalene. It was proposed that the more effective ¼ – ¼ and ¼ –cation
interactionsin the radical cation of the cyclophane caused the above behavior.
Cyclophanes are interesting to theoretical chemists because of their unique struc-
tures and unusual intramolecular interactions . To date, theoretical methods
including molecular mechanics , HMO , CNDO , MNDO , AM1 ,
PM3 , MS-X
, and ab initio calculations  have been used on various cy-
clophanes, whose major aim is usually to know whether or not a particular theoreti-
cal method can reproduce the experimental structure and predict the corresponding
Recently, Iyoda et al. successfully synthesized 1,8-[1,8-naphthalenediylbis(4
4-biphenyl-diyl)]naphthalene 1 (Fig. 1), which is a very stable strained cyclophane
and represents the rst example in which two biphenyl rings are held so rigidly that
they strongly interact with each other via a
stacking . Interestingly, it was
also found that though 1 was fairly easily oxidized, smaller related compounds such
as 1,8-bisphenyl-naphthalene 2 were not.
To whom correspondence should be addressed.