TY - JOUR
T1 - Molecular engineering. 8.1 Kinetic and conformational studies of resorcin[4]arene-based C4 tetraoxatetrathiahemicarceplexes
T2 - Carceroisomerism and twistomerism
AU - Paek, K.
AU - Ihm, H.
AU - Yun, S.
AU - Hee Cheon Lee, Cheon Lee
AU - Kyoung Tai No, Tai No
PY - 2001/8/24
Y1 - 2001/8/24
N2 - New C4v tetraoxatetrathiahemicarcerands and their six hemicarceplexes containing DMF, DMA, DMSO, or NMP were synthesized and characterized. Their conformations, kinetic properties, carceroisomerism, and twistomerism were studied by VT, 2D COSY, NOESY, and ROESY 1H NMR experiments. The decomplexation rates of DMF or DMA were very slow with high activation energy barriers (73 and 104 kJ mol-1, respectively) and the complexed guests feel more constriction than their free liquid state. The largest isomerization energy barrier of carceroisomers was 15.4 kcal mol-1, and the isomerization energy barriers of twistomers are significantly larger than those of carceroisomers.
AB - New C4v tetraoxatetrathiahemicarcerands and their six hemicarceplexes containing DMF, DMA, DMSO, or NMP were synthesized and characterized. Their conformations, kinetic properties, carceroisomerism, and twistomerism were studied by VT, 2D COSY, NOESY, and ROESY 1H NMR experiments. The decomplexation rates of DMF or DMA were very slow with high activation energy barriers (73 and 104 kJ mol-1, respectively) and the complexed guests feel more constriction than their free liquid state. The largest isomerization energy barrier of carceroisomers was 15.4 kcal mol-1, and the isomerization energy barriers of twistomers are significantly larger than those of carceroisomers.
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U2 - 10.1021/jo015594i
DO - 10.1021/jo015594i
M3 - Article
C2 - 11511247
AN - SCOPUS:0035943265
SN - 0022-3263
VL - 66
SP - 5736
EP - 5743
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -