This paper is set to unveil several particulars about the logic embedded in the diachronic model of city
growth and the rules which govern the emergence of urban spaces. The paper outlines an attempt to
detect and define the generative rules of a growing urban structure by means of evaluation techniques.
The initial approach in this regards will be to study the evolution of existing urban regions or cities which
in our case are Manhattan and Barcelona and investigate the rules and causes of their emergence and
growth. The paper will concentrate on the spatial aspect of the generative rules and investigate their
behaviour and dimensionality. Several Space Syntax evaluation methods will be implemented to capture
the change of spatial configurations within the growing urban structures. In addition, certain spatial
elements will be isolated and tested aiming to illustrate their influence on the main spatial structures.
Both urban regions were found to be emergent products of a bottom up organic growth mostly
distinguished in the vicinities of the first settlements. Despite the imposition of a uniform grid on both
cities in later stages of their development these cities managed to deform the regularity in the preplanned
grid in an emergent manner to end up with an efficient model embodied in their current spatial
arrangement. The paper reveals several consistencies in the spatial morphology of both urban regions
and provides explanation of these regularities in an approach to extract the underlying rules which
contributed to the growth optimization process
