Predicting the reactivity of adhesive starting materials

Phenolic compounds are important in the production of bonded-wood products. Phenolic compounds in addition to phenol and resorcinol are potential alternative feedstocks for producing adhesives. The reactivity of a wide variety of phenolic compounds with formaldehyde was investigated using semi-empirical and ab initio computational chemistry methods. Results of these calculations were compared with experimental data. The results indicate that ab initio computational chemistry methods coupled with newer methods for calculating atomic charges can be used to explain the relative reactivities of phenolic compounds with formaldehyde. These methods allow the separation of experimental rate constants into contributions that: can be associated with each reactive center in proportion to the atomic charge at that reactive center. The methods not only correlate the reactivity of previously studied compounds but appear capable of predicting the reactivity of other compounds as well.