Azines. A theoretical study of. pi. -electron delocalization

Journal Article · Wed Jun 07 04:00:00 EDT 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00194a006· OSTI ID:7197252

Wiberg, K B; Nakaji, D; Breneman, C M ^[1]

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1. Yale Univ., New Haven, CT (USA)

{pi}-electron delocalization in benzene and the azines has been studied theoretically in several ways: via an analysis of the first {pi} {yields} {pi}* transitions, via calculation of hydrogenation energies, and via an analysis of the wave functions. The electronic transitions suggest that the delocalization energies are essentially the same for all the compounds. The calculated energies for the addition of 1 equiv of hydrogen suggest that the resonance energies of benzene, pyridine, pyrazine, and pyrimidine are essentially the same. The values for the other azines appear to be smaller, but this may in part arise from changes in the {sigma}-systems. The distribution of {pi}-electron density around the rings does not appear to be strongly perturbed by the replacement of CH by N.

• OSTI ID: 7197252
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:12; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400000* -- Chemistry
400201 -- Chemical & Physicochemical Properties
99 GENERAL AND MISCELLANEOUS
990200 -- Mathematics & Computers
AROMATICS
AZINES
BENZENE
CALCULATION METHODS
DATA
ELECTRONIC STRUCTURE
FUNCTIONS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
MATHEMATICAL MODELS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
THEORETICAL DATA
WAVE FUNCTIONS