Biliazine: a ring open phthalocyanine analog with a meso hydrogen bond
Briana R Schrage1, Victor N Nemykin2, Christopher J Ziegler1
1Department of Chemistry, The University of Akron Akron, Ohio, 44312-3601, USA. ziegler@uakron.edu.
Abstract:
The hemiporphyrazine type chelate and phthalocyaninine analog biliazine (H2BlzH) and its metal complexes can be synthesized in one-step from a monosubstituted diiminisoindoline (DII). This singly substituted precursor is produced from the reaction of unsubstituted DII and 2-aminopyrazole. The biliazine macrocycle is a tetradentate chelate where the ring is closed via a strong hydrogen bond at the meso position. Although the hydrogen bond closes the ring, there is little evidence for 18-electron type annulene aromaticity across the macrocycle, as seen in the UV-visible and MCD spectra and supported by DFT calculations.
More Related Videos
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Basicity of Heterocyclic Aromatic Amines
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene


