Arrow pushing

Arrow pushing is a diagrammatic method for representing electron-pair movement during chemical reactions with curved arrows. It connects changes in bonding to the redistribution of electrons.

Curved-arrow notation: A notation using curved arrows to show electron-pair movement in chemical reactions. Its arrow tails and heads specify the electron source and destination in each step.
Lewis structure: A diagram showing atoms, bonds, and valence electrons in a molecule or ion. Arrow pushing starts from this map of bonds and electron pairs.
Fishhook arrow: A curved arrow with one barb that represents the movement of a single electron. It contrasts with the two-electron arrows used for ordinary electron-pair movement.
Organic synthesis: The construction of organic compounds through planned sequences of chemical reactions. Arrow-pushing analysis helps chemists plan bond-forming steps and anticipate side reactions.
Electron localization function: A function derived from quantum chemistry that maps regions of localized electron pairing and bonding. It offers a computed view of electron organization that can be compared with drawn arrows.
Nucleophilic substitution: A reaction in which a nucleophile replaces a leaving group at an electrophilic center. Its mechanisms show bond formation and bond cleavage as linked arrow-pushing steps.
Valence electron: An electron in an atom’s outer shell that can participate in chemical bonding. Curved arrows track valence electrons as they change bonding or remain as lone pairs.
Reaction coordinate diagram: A graph showing how a reaction system’s energy changes along a reaction pathway. It represents energetic progress, while arrow pushing represents electron redistribution.
Retrosynthetic analysis: A method for planning a synthesis by breaking a target molecule into simpler precursors. Recognizing familiar electron-pair rearrangements helps identify useful disconnections.
Chemical bonding: The interactions that hold atoms together in molecules and extended materials. Arrow diagrams rely on bond and electron-pair concepts whose physical interpretation remains nuanced.

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