Supramolecular structures of six adenine-carboxylic acid complexes

Supramolecular Structures and Tautomerism of Carboxylate Salts of Adenine and Pharmaceutically Relevant N6-Substituted Adenine

“…[13][14][15] Protonation of the 9H-tautomer usually takes place at the N1 nitrogen. 11,[16][17][18][19][20] By contrast, while N 6 -benzyladenine 21 and kinetin 22 crystallize in the expected 9H-tautomeric form, the N3-protonated 7H-tautomer ( Figure 1) was observed in the crystal structures of their bromide, chloride and dihydrogenphosphate salts. [23][24][25][26] In recent years the influence of hydrogen bonding interactions and molecular recognition on tautomeric and protonation equilibria has received growing interest and a few examples have been reported in the literature, where a noncanonical nucleobase tautomer is stabilized by a properly positioned H bond acceptor.…”

“…More recently, more and more structures are emerging where a nucleobase interacts with a complementary small organic molecule to give a hydrogen-bonded network. [10][11][12] Adenine and its derivatives possess both hydrogen bond acceptor and donor functionalities as well as protonatable nitrogens. Furthermore, adenine can exist in different tautomeric forms with the most stable one being the 9H-amino tautomer ( Figure 1).…”

Molecular recognition of caffeine in solution and solid state

“…Co-crystals have emerged as an important tool in the design and construction of solid state materials with tailor-made properties [144][145][146][147][148]. Co-crystals, one of the synthetic targets in crystal engineering, are long known class of compounds [149][150][151].…”

2-Amino-4-methylpyrimidine: A simple supramolecular scaffold for carboxylic acid complexes both in solid and solution states

“…Analysis of the crystal structural packing patterns of hydrogen bonded molecules can also give some insight into the formation of well-defined and stable aggregates from small molecular components in solution [4]. Supramolecular synthesis is currently an active area of research [5] and strategies for the preparation of supramolecular structures and biologically important molecules are being investigated. In our previous work [6], we reported the supramolecular hydrogen bonded network of different architectures of 2-aminopyrimidine with dicarboxylic acids [7].…”