engleski

On the Acidity of Cyclopropanaphthalenes. Gas Phase and Computational Studies

1H-Cyclopropa[b]naphthalene (3H) and 2-methylnaphthalene (6H) were deprotonated by fluoride ion in a Fourier transform mass spectrometer, and their acidities were measured via equilibrium techniques (Delta G˚ acid = 357.5 +- 2.1 (3H) and 365.2 +- 2.1 (6H) kcal mol-1, Delta H˚ acid = 365.1 +- 2.1 (3H) and 372.7 +- 2.1 (6H) kcal mol-1). These results were modeled by MP2 and BVWN5 calculations, and additional computations were carried out on benzocyclopropene (1H), toluene (2H), 1H-cyclopropa[a]naphthalene (4H), and 1-methylnaphthalene (5H). The stability of the conjugate bases of 3H and 4H are examined and their aromatic vs. antiaromatic nature is considered.

aromaticity; antiaromaticity; cycloproparenes; FTMS; ab initio and DFT calculations

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