Hydrogen bonding patterns of calix[4]arenes with thiourea functionalities in solution and in the solid state.
[structure: see text] We have synthesized a number of calix[4]arene derivatives presenting thiourea functional groups at their upper rims by the condensation of a 1,3-di(p-amino)calix[4]arene with alkyl isothiocyanates. Mono- and dithiourea-substituted calix[4]arenes were prepared selectively in good yields, and homocoupling of the former led to calix[4]arene dimers with a thiourea linker. X-ray crystallography revealed interesting intra- and intermolecular hydrogen bonding patterns. (1)H NMR data and computational studies also provided some insight into the hydrogen bonding patterns.
Kim
Su Jeong
SJ
National Research Laboratory, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology, San 31, Hyoja Dong, Pohang 790-784, Korea.
Jo
Moon-Gi
MG
Lee
Jin Yong
JY
Kim
Byeang Hyean
BH
D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry*
D010636:Phenols; D012996:Solutions; C121325:calix(4)arene; D047250:Calixarenes; D013890:Thiourea