TY - JOUR
T1 - The 2-aminopyridinium-carboxylate supramolecular heterosynthon
T2 - A robust motif for generation of multiple-component crystals
AU - Bis, Joanna A.
AU - Zaworotko, Michael J.
PY - 2005/5
Y1 - 2005/5
N2 - An analysis of the Cambridge Structural Database reveals that 77% of compounds that contain both 2-aminopyridine and carboxylic acid moieties generate 2-aminopyridine-carboxylic acid supramolecular heterosynthons rather than carboxylic acid or 2-aminopyridine supramolecular homosynthons. In the absence of other competing functionalities, the occurrence of heterosynthons increases to 97%. This observation is supported by the determination of single-crystal structures of 10 new compounds that contain both a 2-aminopyridine and a carboxylic acid moiety: 2-aminopyridinium 4-aminobenzoate, 1; 2-aminopyridinium isophthalate, 2; bis(2-aminopyridinium) terephthalate, 3; 2-amino-5-methylpyridinium benzoate, 4; bis(2-amino-5-methylpyridinium) 5-tertbutylisophthalate, 5; 2-amino-5-methylpyridimum terephthalate, 6; bis(2-amino-5-methylpyridinium) 2,6-naphthalenedicarboxylate, 7; bis(2-amino-5-methylpyridinium) adipate adipic acid, 8; bis(2-amino-5- methylpyridinium) 2,5-thiophenedicarboxylate 2,5-thiophenedicarboxylic acid, 9; and indomethacin 2-amino-5-methylpyridinium, 10. All 10 compounds are ionic, with proton transfer occurring to the aromatic nitrogen of the 2-aminopyridine moiety. Analysis of the supramolecular synthons and their effect upon crystal packing is presented in the context of crystal engineering and host-guest chemistry.
AB - An analysis of the Cambridge Structural Database reveals that 77% of compounds that contain both 2-aminopyridine and carboxylic acid moieties generate 2-aminopyridine-carboxylic acid supramolecular heterosynthons rather than carboxylic acid or 2-aminopyridine supramolecular homosynthons. In the absence of other competing functionalities, the occurrence of heterosynthons increases to 97%. This observation is supported by the determination of single-crystal structures of 10 new compounds that contain both a 2-aminopyridine and a carboxylic acid moiety: 2-aminopyridinium 4-aminobenzoate, 1; 2-aminopyridinium isophthalate, 2; bis(2-aminopyridinium) terephthalate, 3; 2-amino-5-methylpyridinium benzoate, 4; bis(2-amino-5-methylpyridinium) 5-tertbutylisophthalate, 5; 2-amino-5-methylpyridimum terephthalate, 6; bis(2-amino-5-methylpyridinium) 2,6-naphthalenedicarboxylate, 7; bis(2-amino-5-methylpyridinium) adipate adipic acid, 8; bis(2-amino-5- methylpyridinium) 2,5-thiophenedicarboxylate 2,5-thiophenedicarboxylic acid, 9; and indomethacin 2-amino-5-methylpyridinium, 10. All 10 compounds are ionic, with proton transfer occurring to the aromatic nitrogen of the 2-aminopyridine moiety. Analysis of the supramolecular synthons and their effect upon crystal packing is presented in the context of crystal engineering and host-guest chemistry.
UR - http://www.scopus.com/inward/record.url?scp=19944400821&partnerID=8YFLogxK
U2 - 10.1021/cg049622c
DO - 10.1021/cg049622c
M3 - Article
AN - SCOPUS:19944400821
SN - 1528-7483
VL - 5
SP - 1169
EP - 1179
JO - Crystal Growth and Design
JF - Crystal Growth and Design
IS - 3
ER -