 Computational studies have been performed on the formation of hexahydrotriazines from the reactions of primary amines with formaldehyde. These are models for the synthesis of poly(hexahydrotriazine)s, PHTs and hemiaminal supramolecular networks (HSNS, precursors to PHTs) by the reactions of bisanilines with formaldehyde. Computational studies on possible mechanisms for hexahydrotriazine formation reveals that water-promoted sequential addition of amine with formaldehyde is preferred over mechanisms involving amine self-catalysis of amine addition to formaldehyde involving the [2+2+2] cycloaddition of imine intermediates. These computational studies have also revealed why HSNs are readily formed at relatively low temperatures while PHTs require heating at elevated temperatures (200 �C). Moreover, our investigations have shed light on the experimentally observed greater reactivity of electron-rich amines in comparison with electron-deficient amines in these reactions.

Theoretical investigations on hexhydrotriazine formation from the reactions of amines with formaldehyde

248th National Meeting (2014)

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