Thermodynamic properties of benzyl halides: enthalpies of formation, strain enthalpies, and carbon–halogen bond dissociation enthalpies†
Abstract
The molar enthalpies of formation of benzyl halides PhCH2-X, PhCH(CH3)-X, and PhC(CH3)2-X, where X = F, Cl, Br, and I are in the gaseous state, have been derived by combination of our own thermochemical measurements together with the data available from the literature. These new results have been shown to be internally consistent, and they were used to derive strain enthalpies of benzyl halides as well as for estimation of the carbon–halogen bond dissociation enthalpy in benzyl halides. Strain effects are discussed in terms of deviations of gaseous enthalpies of formation from group additivity rules. Bond dissociation enthalpies (BDE's) of the benzyl halides studied are generally indistinguishable from their alkyl analogs having the same substituent X.
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