TY - JOUR
T1 - Structural study of salicylic acid salts of a series of azacycles and azacrown ethers
AU - Fonari, Marina S.
AU - Ganin, Eduard V.
AU - Basok, Stepan S.
AU - Lyssenko, Konstantin A.
AU - Zaworotko, Michael J.
AU - Kravtsov, Victor Ch
PY - 2010/12/1
Y1 - 2010/12/1
N2 - Interaction of salicylic acid (saH) with the azacycles piperidine (pipe) and meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane (teta) and with the aza-crown ethers aza-12-crown-4 (A12C4), benzoaza-15-crown-5 (BA15C5), aza-18-crown-6 (A18C6), and diaza-18-crown-6 (DA18C6) afforded the proton-transfer complexes (organic salts) of compositions [pipeH][sa], [tetaH2][sa]2, [A12C4H][sa], [BA15C5H][sa], [A18C6H][sa]•2H2O, and [DA18C6H2][sa] 2•3H2O, whose structures were determined by a single crystal X-ray method. These products were also obtained by the same synthetic conditions starting from acetylsalicylic acid (aspirin) as a result of hydrolysis. The charge-assisted N-H•••O hydrogen-bond provides the main driving force for direct binding of sa with cyclic azonia cations. The crystal packing is also supported by weak C-H•••O hydrogen bonding and edge-to-face π•••π intermolecular interactions.
AB - Interaction of salicylic acid (saH) with the azacycles piperidine (pipe) and meso-5,7,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane (teta) and with the aza-crown ethers aza-12-crown-4 (A12C4), benzoaza-15-crown-5 (BA15C5), aza-18-crown-6 (A18C6), and diaza-18-crown-6 (DA18C6) afforded the proton-transfer complexes (organic salts) of compositions [pipeH][sa], [tetaH2][sa]2, [A12C4H][sa], [BA15C5H][sa], [A18C6H][sa]•2H2O, and [DA18C6H2][sa] 2•3H2O, whose structures were determined by a single crystal X-ray method. These products were also obtained by the same synthetic conditions starting from acetylsalicylic acid (aspirin) as a result of hydrolysis. The charge-assisted N-H•••O hydrogen-bond provides the main driving force for direct binding of sa with cyclic azonia cations. The crystal packing is also supported by weak C-H•••O hydrogen bonding and edge-to-face π•••π intermolecular interactions.
UR - http://www.scopus.com/inward/record.url?scp=78649913031&partnerID=8YFLogxK
U2 - 10.1021/cg101002x
DO - 10.1021/cg101002x
M3 - Article
AN - SCOPUS:78649913031
SN - 1528-7483
VL - 10
SP - 5210
EP - 5220
JO - Crystal Growth and Design
JF - Crystal Growth and Design
IS - 12
ER -