Hydrogen Bonding Patterns of Calix[4]arenes with Thiourea Functionalities in Solution and in the Solid State

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 homocoup...

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Published inOrganic letters Vol. 6; no. 12; pp. 1963 - 1966
Main Authors Kim, Su Jeong, Jo, Moon-Gi, Lee, Jin Yong, Kim, Byeang Hyean
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.06.2004
Amer Chemical Soc
Subjects
Calixarenes - chemical synthesis
Calixarenes - chemistry
Chemistry
Chemistry, Organic
Hydrogen Bonding
Models, Chemical
Molecular Conformation
Phenols - chemical synthesis
Phenols - chemistry
Physical Sciences
Science & Technology
Solutions - chemistry
Thiourea - chemistry
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Summary: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. 1H NMR data and computational studies also provided some insight into the hydrogen bonding patterns.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol049497y