TY - JOUR
T1 - Cyclic-tri(N-methyl-meta-benzamide)s
T2 - Substituent effects on the bowl-shaped conformation in the crystal and solution states
AU - Kakuta, Hiroki
AU - Azumaya, Isao
AU - Masu, Hyuma
AU - Matsumura, Mio
AU - Yamaguchi, Kentaro
AU - Kagechika, Hiroyuki
AU - Tanatani, Aya
PY - 2010/10/16
Y1 - 2010/10/16
N2 - Cyclic trimers of 3-(N-alkylamino)benzoic acid (calix[3]amides) with various substituents at the meta position of the phenyl rings were synthesized and the effects of the substituents on the crystal structures and energy profiles in solution were examined. The calixamides existed in a syn conformation in the crystal state, and this was also the major conformation in solution, especially in polar solvents. The energy barrier between syn and anti conformers in the solution was not significantly affected by substituents (12.7-14.0 kcal/mol). The effect of the substituent on the temperature dependence of the syn/anti ratio are discussed.
AB - Cyclic trimers of 3-(N-alkylamino)benzoic acid (calix[3]amides) with various substituents at the meta position of the phenyl rings were synthesized and the effects of the substituents on the crystal structures and energy profiles in solution were examined. The calixamides existed in a syn conformation in the crystal state, and this was also the major conformation in solution, especially in polar solvents. The energy barrier between syn and anti conformers in the solution was not significantly affected by substituents (12.7-14.0 kcal/mol). The effect of the substituent on the temperature dependence of the syn/anti ratio are discussed.
KW - Aromatic-aromatic interactions
KW - Calix[3]amide
KW - Substituent effect
KW - Syn-anti conformation
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U2 - 10.1016/j.tet.2010.08.049
DO - 10.1016/j.tet.2010.08.049
M3 - Article
AN - SCOPUS:77957192377
VL - 66
SP - 8254
EP - 8260
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 42
ER -