<p>Life presents a profound scientific challenge. Understanding the interplay between chaos, entropy dynamics, and Prigogine’s dissipative systems provides insight into how order emerges and persists far from equilibrium. Beyond classical thermodynamic dissipation, we propose an <i>informational</i> dissipative structure rooted in water topology, whose dynamic hydrogen-bond networks encode Shannon entropy and support autopoiesis and regeneration. This study explores how Prigogine-like informational dissipative systems interact with chaotic dynamics to stabilize and prolong complexity. We focus on entropy cycling between water topology (Shannon space) and molecular systems (Boltzmann space), emphasizing <i>disquisotropic entropy</i>—a hidden, accumulative reservoir formed by repeated molecular interactions in water. Using nonlinear ordinary differential equations, modified Lorenz systems, and Python-based simulations, we model how entropy and chaos co-evolve in water-mediated molecular contexts. Our results show that chaos enhances, rather than disrupts, system stability by delaying thermodynamic equilibrium and promoting structural reorganization. Shannon-type entropy dissipates iteratively, fueling molecular complexity, while chaotic feedback—driven by fluctuating water topology—sustains autopoietic cycles. Disquisotropic entropy modulates and is shaped by this feedback, supporting prolonged system renewal. We propose that informational dissipative systems are inherently chaotic, with chaos acting as a generative force for self-organization. Coupling Landauer’s principle with chaotic entropy modulation, we present a framework uniting thermodynamics, information theory, and nonlinear dynamics. This model shows how disorder sustains order through structured entropy flows—a core feature of life and complex adaptive systems.</p>