N-acylhydrazones (NAH) are distinguished by the presence of an azomethine fragment (CO-NH-N=CH), which, when integrated or connected into a heterocyclic scaffold, frequently yields compounds exhibiting noteworthy biological activities, including anticancer, antibacterial, and antidepressant properties. Acrylohydrazides, a distinct class within these organic compounds, have recently garnered attention due to their multifunctional properties. Among them, (E)-3-(furan-2-yl) acrylohydrazides stand out, featuring the conjugated furan-2-yl scaffold linked to a hydrazide function. This unique combination of structures holds considerable potential for diverse applications, encompassing both bioactive functionalities and within the realm of optoelectronic conduction. The electronic conjugation intrinsic to these molecules can significantly influence charge transport properties, offering opportunities for exploitation in the development of optoelectronic devices such as organic light-emitting diodes (OLEDs), and organic fieldeffect transistors (OFETs). Building upon our prior studies, which consistently established the stable (E) conformation of N-acylhydrazones in various solvents, particularly the prevalence of the syn conformation in solvents like DMSO-d6, we identified conditions favoring the anti conformation, including less polar solvents (e.g., CDCl3), intramolecular hydrogen bonding, or steric hindrance. The persistent dominance of the syn conformation, where crucial substituents adopt specific spatial orientations, suggests a structural regularity with promising implications for the design of novel molecules tailored for specific purposes.