ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
peri-Bridged naphthalenes in which the C-1 and C-8 atoms of the naphthalene ring are bonded to a single atom in a bridging group Z (Z = CH2, CHBr, C=O, NH, O, S, S=O and SO2) were studied by the AM1 semi-empirical SCF MO method. Although in peri-naphthalenes bridged by carbon or sulfur the naphthalene structure is planar, the corresponding nitrogen- or oxygen-bridged molecules are distorted about 15 and 23°, respectively. There are significant variations (from 92 to 106°) of the C-1-C-9-C-8 angle that is calculated in the cycle formed by the bridge. The calculated strain-energy barrier for pyramidal atom inversion in amine 4 and sulfoxide 7 are 32·5 and 174 kJ mol-1, respectively.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610081008
