The aim of this article is the characterization of the ancient Greek postpositive particles and enclitic expressions in terms of a rule based derivational model of prosodic phonology. The study compares Goldstein’s (2016a) generalized enclisis approach (GE) with the generalized postpositive approach (GP) adopted, among others, by Dover (1960). Both views involve an interpretation of the second-position (or Wackernagel’s position) phenomenon, as well as a taxonomy of second-position expressions in ancient Greek. As a central topic, the analysis considers the behavior of the modal particle ἄν. Concerning such issue, the work shows some inaccuracies implied by the GE idea that ἄν is enclitic, and argues that such flaws are absent from the GP t...