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Topological Classification and Supramolecular Chirality of 2 1 ‐Helical Ladder‐Type Hydrogen‐Bond Networks Composed of Primary Ammonium Carboxylates: Bundle Control in 2 1 ‐Helical Assemblies
Author(s) -
Yuge Tetsuharu,
Sakai Tatsuya,
Kai Nobuyasu,
Hisaki Ichiro,
Miyata Mikiji,
Tohnai Norimitsu
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701709
Subject(s) - chirality (physics) , supramolecular chemistry , topology (electrical circuits) , hydrogen bond , crystallography , carboxylate , molecule , chemistry , helicity , crystal structure , stereochemistry , physics , mathematics , symmetry breaking , quantum mechanics , chiral symmetry breaking , organic chemistry , combinatorics , nambu–jona lasinio model
The supramolecular chirality of 1D ladder‐type hydrogen‐bond networks composed of primary ammonium carboxylates was determined based on topological considerations. Chirality in such networks is based on the absolute configuration of the primary ammonium cation, which arises from discrimination between the two oxygen atoms of the carboxylate anion. The configurations of the cations and anions generate topological diversity in the networks, which are classified into six subgroups. In the Cambridge Structural Database, salts based on ladder type 1 constitute over 70 % of salts with a 1D‐ladder‐type network. Ladder type 1 , based on a 2 1 ‐axis, is not superimposable on its mirror image, which leads to the first definition of right‐ or left‐handedness of 2 1 ‐helicity on the basis of supramolecular tilt chirality. Helical assemblies of 2 1 ‐type with triaxial chirality can be assembled in various ways to yield chiral bundles and crystals. On the basis of these considerations, we constructed clay mimic structures with several bundle patterns by connecting the hydrogen‐bond networks by using bifunctional molecules. These results open up the possibility of in‐depth crystal engineering based on hydrogen‐bond topology.