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Gas Phase Deprotonation Study of Naphtho[a]cyclobutenone and Naphtho[b]cyclobutenone (CROSBI ID 507651)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa

Eckert-Maksić, Mirjana ; Vazdar, Mario ; Glasovac, Zoran ; Fattahi, A. ; Kass, S.R. Gas Phase Deprotonation Study of Naphtho[a]cyclobutenone and Naphtho[b]cyclobutenone // 10th European Symposium on Organic Reactivity : Book of Abstracts / Speranza, Maurizio (ur.). Rim, 2005. str. 91-91

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

Povezanost rada

Kemija