H-Bridges with OH Donors in Organic Chemistry

Abstract This article discusses the H-bridge formation amongst functional groups containing different H-bridge acceptors with OH donors. A series of circular grids is introduced as a visual aid for the organization and the comparison of the diversity of H-bridges present in organic molecules, emphasizing in the case where the H-bridge donor is an OH group (primarily alcohols and phenols). The H-bridges are classified as “unlikely”, “less significant” and “significant” based on experimental and/or theoretical evidence, and analyzed in terms of electronic, steric, thermodynamic, substitutional, or situational effects. Using these grids, students can predict and classify the likeliness of an H-bridge interaction between common organic molecules and understand their effects in more complex systems.