Gas phase acidity of substituted benzenes

作者：Bouchoux Guy^*

来源：Chemical Physics Letters, 2011, 506(4-6): 167-174.

DOI：10.1016/j.cplett.2011.03.032

Deprotonation thermochemistry of benzene derivatives C(6)H(5)X (X = H, F, Cl, OH, NH(2), CN, CHO, NO(2), CH(3), C(2)H(5), CHCH(2), CCH) has been examined at the G3B3 level of theory. For X = F, Cl, CN, CHO and NO(2), the most favorable deprotonation site is the ortho position of the phenyl ring. This regio-specificity is directly related to the field/inductive effect of the substituent. G3B3 gas phase acidities, Delta(acid)H degrees and Delta(acid)G degrees, compare within less than 4 kJ mol (1) with experimental data. A noticeable exception is nitrobenzene for which tabulated acidity appear to be underestimated by ca. 120 kJ mol (1).

• 出版日期2011-4-20