Naslov
Benzocyclobutene: The Impact of Fusing a Strained Ring onto Benzene

Autori
Glasovac, Zoran ; Eckert-Maksić, Mirjana ; Broadus, Katherine, M. ; Hare, Michael, C. ; Kass, Steven, R.

Izvornik
The Journal of Organic Chemistry 65 (2000), 6; 1818-1824

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Benzocyclobutene; acidity; Mass Spectrometry; Ion Cyclotron Resonance; electronic structure; ab initio; quantum-chemical calculations

Sažetak
The gas-phase acidities of the two aromatic sites in benzocyclobutene were measured in a Fourier transform mass spectrometer using kinetic technique (i.e. DePuy method). Fusion of a cyclobutane ring onto benzene is found to have slight acidifying effect at the alpha position (3.2 +/- 1.7 kcal/mol) and little, if any, influence on the beta site (0.8 +/- 1.9 kcal/mol). Energetic data (acidity, electron affinity and C-H bond dissociation energy) for the benzylic position were obtained via the bracketing technique and application of a thermodynemic cycle. Differences in the reactivities of the three conjugate bases also were explored. Ab initio and DFT calculations were carried out to provide geometries, energies and insights into the carbanions' electronic structures.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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