Ring stacking and laddering in ammonium carboxylate salts: extension to secondary ammonium salts

Abstract

<p>A combined CSD and experimental study shows that the ring stacking and laddering principle, an ionic model, gives insight into the crystal structures of secondary ammonium carboxylate salts.</p>

The crystal structures of benzylammonium phenylacetate and its hydrate

“…7b). Such a motif is common in ammonium carboxylate salts (Odendal et al, 2010). Evidently, the presence of crystal water in 2 leads to a change in the hydrogen-bonding system compared to 1.…”

“…aromatic residues) play an important role in the formation of self-assembled structures of (di)peptides or amino acids (Gö rbitz, 2010;Mossou et al, 2014;Reches & Gazit, 2003). Similarly, the packing motifs of ammonium carboxylate salts are governed by the formation of hydrogen-bonded networks between the ammonium and carboxylate groups, as well as the nature of the residues of the ammonium and carboxylate residues (Kinbara et al, 1996;Odendal et al, 2010).…”

Synthesis and Characterization of Hypercoordinated Silicon Anions: Catching Intermediates of Lewis Base Catalysis

“…The O5À C13 bond length of 1.322(2) Å is considerably elongated, and the O6À C13 bond of 1.196(3) Å is shortened compared to "free" formate (1.2400(15) and 1.2429 (14) Å in [H 2 NCy 2 ][HCO 2 ]). [33] Again, [Na@15-c-5][HCO 2 -B(C 6 F 5 ) 3 ] exhibits a less disturbed C=O (1.222(4) Å) and CÀ O bond (1.302(3) Å). [21,34] In the acetate adduct [H 3 CCO 2 -1] À , the Si1À O1 bond lengths are almost equal (1.690(3) as in [HCO 2 -1] À (Figure 4b).…”

The role of attractive and repulsive interactions in the stabilization of ammonium salts structures

“…Haynes et al 18 following their previous studies on rationalizing and predicting general packing motifs of ammonium carboxylate salts extend this analysis to other models and present insights into the structural motifs of these structures from the perspective of ring-stacking and ring-laddering concept. The authors highlight that the literature focuses on hydrogen bonding patterns and the lack of analysis of organic salts in terms of electrostatic interactions, which may provide new insights into the factors that govern the crystal formation of organic salts.…”

“…The authors highlight that the literature focuses on hydrogen bonding patterns and the lack of analysis of organic salts in terms of electrostatic interactions, which may provide new insights into the factors that govern the crystal formation of organic salts. 18 In this context, our research group took the first step into the study of charged molecules when reported the evaluation of the crystalline organization of imidazolinium dicationic ionic liquids (ILs) considering the stabilization energies and contact areas between the central dicationic unit and all anions that had the contact area with this dication. 19 The supramolecular cluster (SC) 20 was used as a demarcation of the analysis and it was shown that all interactions contribute similarly to the stabilization of the crystal structure.…”