Residual electronegativity - an empirical quantification of polar influences and its application to the proton affinity of amines
✍ Scribed by Michael G. Hutchings; Johann Gasteiger
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 236 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The residual electronegativity of an atom in a molecule can be used as a quantitative mecsure odf the polar influence of a substituent on reactivity, as exemplifiedby its ability, with substituent polarisability, to coTrelate the proton affinity data of 80 amines.
A cornerstone of organic chemistry is
the notion that there exist fundamental relationships between the structure of a molecule and its chemical reactivity. Concepts like inductive, resonance, steric, polarisability and solvent effects have been invoked in a qualitative manner, whereas the quantitative treatment has centred around linear free energy relationships (LFER). With LFER, correlations are sought between two sets of reactivity data, the reaction under investigation, and a standard one. Although this empirical approach has been quite successful some serious problems still exist. The artificial separation of a structure into substituent, skeleton