The application of mass spectrometry to a quantitative characterisation of the electronic and steric effects in organic compounds-I: The transmission of substituent influence through the chain of conjugated double bonds.

Autor: Zolotarev, B. M., Yanovskaya, L. A., Umirzakov, B., Chizhov, O. S., Kucherov, V. F.
Zdroj: Organic Mass Spectrometry; 1971, Vol. 5 Issue 9, p1043-1048, 6p
Abstrakt: The mass spectra of polyenic compounds of the type RC6H4(CH=CH)nCOPh, n=1, R=H,p-NMe2,p-OH,p-OMe,p-Cl,p-Br,p-NO2,m-NO2; n=2, R=H, p-NMe2, p-OMe,p-Cl,p-Br, p-NO2; n = 3, R = H, p-OMe,p-Cl, p-Br,p-No2 have been measured. The ratio of the intensities of the common ion PhCO (m/e 105) to the intensities of the molecular ions for these series is correlated with the Hammett-Brown equation with reaction constants p = 0.73 (when n = 1), 0.25 (when n =2), 0.11 (when n = 3). The transmission coefficients were calculated as π'=0.72,0.25 and 0.11 respectively [assuming p=1.01 for benzophenone series-see M. M. Bursey and F. W. McLafferty, J. Am. Chem. Soc. 89, 1 (1967)]. The contributions of the inductive mesomeric direct polar conjugation and non-additive interaction were calculated in accordance with the equation log Z/Z0= [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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