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1,2,4,5‐Tetrazines vs. Carboxylic Acid Dimers: Molecular Chemistry vs. Supramolecular Chemistry
Author(s) -
Infantes Lourdes,
Mahon Mary F.,
Male Louise,
Raithby Paul R.,
Teat Simon J.,
Sauer Jürgen,
Jagerovic Nadine,
Elguero José,
Motherwell Sam
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390104
Subject(s) - chemistry , synthon , supramolecular chemistry , carboxylic acid , hydrogen bond , covalent bond , crystal engineering , intermolecular force , ring (chemistry) , supramolecular assembly , molecule , crystallography , polymer chemistry , crystal structure , stereochemistry , organic chemistry
The structures of six new tetrazines have been determined and their molecular packing has been compared to the supermolecular architecture observed in related carboxylic acid dimers. In the tetrazines, covalent NN bonds are considered to replace the intermolecular OH⋅⋅⋅O hydrogen bonds of the carboxylic acids. In the systems investigated, it is apparent that, in the majority of cases, the covalent six‐membered ring of the tetrazine is an appropriate replacement for the carboxylic acid synthon. This apparent interplay between molecular and supramolecular units may have applications in the crystal engineering of new materials.