J. Gasteiger et al., ANALYSIS OF THE REACTIVITY OF SINGLE BONDS IN ALIPHATIC MOLECULES BY STATISTICAL AND PATTERN-RECOGNITION METHODS, Journal of chemical information and computer sciences, 33(3), 1993, pp. 385-394
The polar breaking of a bond is the initiating step in many organic re
actions. The factors influencing the heterolysis of a bond are investi
gated by a series of statistical and pattern recognition methods. The
power of a variety of methods-including principal component analysis,
linear discriminant analysis, cluster analysis, k-nearest-neighbor ana
lysis, and logistic regression analysis-for understanding and predicti
ng the reactivity of bonds based on electronic and energy parameters i
s elaborated. In particular, we show how information on whether a seri
es of bonds will undergo heterolysis or not can be used to derive a fu
nction quantifying polar reactivity. In the end, an equation is develo
ped that allows the prediction of the polar breaking of bonds for a wi
de range of aliphatic structures.