Uncovering foundational insights through data-driven methods into CA-based cocrystals. Chloranilic acid (CA) (Figure ) is a particularly versatile platform for forming polar cocrystals, due to its dual role as both a proton donor and acceptor. This characteristic enables CA to 15 participate in a variety of hydrogen-bonding motifs, making it a crucial molecular scaffold for polar crystal engineering. The directional nature of these hydrogen bonds facilitates the generation of polar moments, further enhancing its role in cocrystal formation. During co-crystallization, CA exhibits remarkable chemical flexibility, adopting neutral, monovalent, and divalent deprotonated forms. This adaptability enables the formation of robust intra-and intermolecular hydrogen bonds, facilitated by 20 keto-enol tautomerization. The keto-enol tautomerization of CA, characterized by shifts between keto (C=O) and enol (C-OH) configurations, enables fine-tuning of hydrogen-bonding interactions depending on the crystallization environment. This dynamic behavior not only stabilizes the resulting cocrystals but also induces spontaneous polarization, a key feature in designing materials with advanced functional properties. A notable example is the cocrystal of chloranilic acid and 25 phenazine (CA-Phz), an organic ferroelectric material in which polarization direction is governed by the alignment of hydrogen bonds. Polarization reversal in this system occurs via proton transfer along these bonds, demonstrating the potential of CA-based systems for functional applications.