Organic Layered Crystals with Adjustable Interlayer Distances of 1-Naphthylmethylammonium <i>n</i>-Alkanoates and Isomerism of Hydrogen-Bond Networks by Steric Dimension

A series of 1-naphthylmethylammonium n-alkanoates from acetate to triacontanoate produce isomorphic layered structures in the crystalline state. The interlayer distances, d-spacings, are proportional to the lengths of the alkyl chains. This is attributed to synergic intermolecular interactions; π−π and CH−π interactions of the naphthalene rings between the cations, hydrophobic interactions of the alkyl chains, and two-dimensional hydrogen-bond networks between the primary ammonium cations and the carboxylate anions. Salts made from carboxylic acids wider than 5.5 Å in the cross sections produce another columnar structure with a one-dimensional ladder-type hydrogen-bond network. Steric parameters of the acid components provide an explanation for the isomerism of the hydrogen-bond network.