Photoelectron Spektra of Azabenzenes and Azanaphthalenes: II. A Reinvestigation of Azanaphthalenes by High-Resolution Photoelectron Spectroscopy

✍ Scribed by F. Brogli; E. Heilbronner; T. Kobayashi

• Publisher: John Wiley and Sons
• Year: 1972
• Tongue: German
• Weight: 662 KB
• Volume: 55
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19720550131

✦ Synopsis

Abstract

The bands with I~v~ < 13 eV in the photoelectron spectra of quinoline (IX), isoquinoline (X), cinnoline (XI), quinazoline (XII), and quinoxaline (XIII) have been reassigned in a way consistent with the assignment proposed for pyridine (II), the diazines (III, IV, V), s‐triazine (VI), and 1,2,4,5‐tetrazine (VII). The bands corresponding to the ejection of an electron from a π‐orbital have been identified by a regression calculation based on a HMO perturbation treatment. It has been found that the combined through‐space and through‐bond interaction of the lone pairs in III, IV, V and in their corresponding benzologues XI, XII, XIII are the same within experimental error ( ±, 0.2 eV). Our assignment is also supported by an empirical correlation of the pK~a, 1−~ values and the mean lone‐pair ionization potentials of the azaderivatives I to XIII.