Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 24, No. 9, 1986, pp.2545-2552
Published online, 1st January, 1970
DOI: 10.3987/R-1986-09-2545
The Electrophilic Substitution of Heteroaromatic Compounds. Part 53. The Experimental Orientation in the Electrophilic Substitution of 1-Phenylpyridinium Cations, and a Theretical Treatment of Electrophilic Substitution Orientations in N-Phenylheterocycles

Alan R. Katritzky,* Hassan M. Faid-Allah, Hudson Luce, Mati Karelson, and George P. Ford

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, P. O. Box 117200, Gainesville, FL 32611-7200, U.S.A.


Nitration, sulfonation and bromination of the title compound occur in the meta position of the 1-phenyl group. This meta substitution, and the para substitution previously observed for other N-phenylheterocycles, cannot be explained by static reactivity indices. However, a MNDO analysis, taking account of the near degeneracy of the two top HOMO’s, and using experimentally probable interannular anglee, allows rationalization of the orientations observed.