Theoretical study of the triplet state aryl cations recombination: A possible route to unusually stable doubly charged biphenyl cations

Theoretical study of the triplet state aryl cations recombination : A possible route to unusually stable doubly charged biphenyl cations

QC 20140117
The self-recombination reactions of 4-aminophenyl cations and parent phenyl cations, each in ground triplet states, are studied within the framework of density functional theory. Only the total zero spin (singlet state) is chosen, as the quintet and triplet counterparts are nonreactive in these systems. The recombination products are the benzidine and biphenyl doubly charged cations. These species are unexpectedly stable. The transition state of the 4-aminophenyl cations reaction is located at the distance of about 4.0 Å between the ipso-carbon atoms. The activation barrier is predominantly formed by electrostatic repulsion between two cations and is estimated to be 27.6 kcal mol−1 [B3LYP/6–311+G(d,p)]. Similar results are obtained for the phenyl cations recombination. The general importance of the participation of other aryl cations in analogous organic reactions is discussed.

NATURVETENSKAP Biologi Biokemi och molekylärbiologi hsv//swe
NATURAL SCIENCES Biological Sciences Biochemistry and Molecular Biology hsv//eng
aryl cation
biphenyl derivative
organic dication
self-recombination
triplet state
Aryl cations
Biphenyl derivatives
Dications
Condensed matter physics
Molecular physics
Quantum chemistry
Positive ions

Ingår i:International Journal of Quantum Chemistry: Wiley113:24, s. 2580-25880020-76081097-461X

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