By Carey F., Sundberg R.
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Additional resources for Advanced Organic Chemistry. Structure and Mechanisms
All of these factors play an important role in the gas phase and in solution . It was found experimentally that the protonation of guanidine occurs at the imino nitrogen, as the amino nitrogen is less basic than the imino nitrogen atom by $30 kcal mol À1. Guanidines 25 The solution basicity of guanidine is larger than its gas phase basicity. Solvation effects are highly important in determining this difference. The enthalpy of hydration depends on the number of hydrogen atoms linked to the nitrogen atom(s), the size of the neutral and ionic species, and the charge dispersion in the ionic form.
The proton affinity of a base is defined as the negative change of enthalpy (PA ¼ ÀDHprot) associated with the protonation reaction B þ (Hþ ! BHþ), while the absolute gas phase basicity corresponds to the negative of the Gibbs free energy change, that is, GBðBÞ ¼ ÀDGoprot . For estimation of PAs and GBs in the gas phase, high level Hartree-Fock (HF), post-HF and DFT quantum-chemical calculations were employed. It has been found that the quality of obtained geometry is not crucial if PAs are estimated by single-point calculations at higher levels of theory, which is the approach generally used.
Then, the pKa values were estimated by a linear regression model of the experimental pKa data and calculated APA(solv). 7. It should be noted that such linear relations of pKa are valid for each computational level and each family of compounds separately, hence they should be derived in each case [85,111–113]. 9 Concluding Remarks In summary, guanidinophosphazenes belong to the most basic, experimentally determined class of superbases, followed by phosphazenes, proazaphosphatranes and guanidines.
Advanced Organic Chemistry. Structure and Mechanisms by Carey F., Sundberg R.