This research explores the descriptive and generative potentials of shape grammars to unveil the order of urban morphological complexity underlying Portuguese treatises and the knowledge embedded in Portuguese urban cartographic representations of architecture and military engineering from the 16th to the 18th century. The shape grammar made it possible to infer the grammatical rules of composition based on the written descriptions provided by Portuguese treatises, as well as to decode the geometry of ideal urban plans and built cities. This research suggests that the historical cities, both built and ideal were based on a structured knowledge-based process from where it is possible not only to retrieve a generative parametric urban grammar – UrbanGENE – but also to construct 2D shape grammar interpreter, which is capable of iteratively generating Portuguese planimetric proportional and symmetrical urban systems. This suggests that the knowledge and computational tools achieved could be successfully deployed in teaching and learning of urban history.

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