Gas Phase Deprotonation Study of Naphtho[a]cyclobutenone and Naphtho[b]cyclobutenone (CROSBI ID 507651)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa
Podaci o odgovornosti
Eckert-Maksić, Mirjana ; Vazdar, Mario ; Glasovac, Zoran ; Fattahi, A. ; Kass, S.R.
engleski
Gas Phase Deprotonation Study of Naphtho[a]cyclobutenone and Naphtho[b]cyclobutenone
Structure and reactivity of the conjugate bases of naphtho[a]- (1) and naphtho[b]cyclobutenone (2) are of considerable interest in view of their potential antiaromatic character, which should considerably affect their properties. In this contribution we report results of a Fourier transform mass spectrometry study and ab initio calculations of these anions. The anion 1a was generated by deprotonation of 1 by fluoride ion. Under similar conditions deprotonation of 2 with a strong base (e.g. OH^-) led to a mixture of enolate anion 2a and the conjugate base of naphthyl ketene (2b). The gas phase energetic data of the studied species (PA, EA, BDE(C-H)), as obtained by the bracketing techniques and thermodynamic cycles, will be discussed and compared with the previously published results for the benzocyclobutenone enolate. In addition, mechanism of formation of 2b will be elaborated.
naphtho[a]cyclobutenone; naphtho[b]cyclobutenone
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Podaci o prilogu
91-91.
2005.
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objavljeno
Podaci o matičnoj publikaciji
10th European Symposium on Organic Reactivity : Book of Abstracts
Speranza, Maurizio
Rim:
Podaci o skupu
European Symposium on Organic Reactivity (10 ; 2005)
predavanje
25.07.2005-30.07.2005
Rim, Italija