Cyclic-tri(N-methyl-meta-benzamide)s: Substituent effects on the bowl-shaped conformation in the crystal and solution states

Hiroki Kakuta; Isao Azumaya; Hyuma Masu; Mio Matsumura; Kentaro Yamaguchi; Hiroyuki Kagechika; Aya Tanatani

doi:10.1016/j.tet.2010.08.049

Cyclic-tri(N-methyl-meta-benzamide)s: Substituent effects on the bowl-shaped conformation in the crystal and solution states

Hiroki Kakuta, Isao Azumaya, Hyuma Masu, Mio Matsumura, Kentaro Yamaguchi, Hiroyuki Kagechika, Aya Tanatani

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	8254-8260
Number of pages	7
Journal	Tetrahedron
Volume	66
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2010.08.049
Publication status	Published - Oct 16 2010

Keywords

Aromatic-aromatic interactions
Calix[3]amide
Substituent effect
Syn-anti conformation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Cyclic-tri(N-methyl-meta-benzamide)s : Substituent effects on the bowl-shaped conformation in the crystal and solution states. / Kakuta, Hiroki; Azumaya, Isao; Masu, Hyuma; Matsumura, Mio; Yamaguchi, Kentaro; Kagechika, Hiroyuki; Tanatani, Aya.

In: Tetrahedron, Vol. 66, No. 42, 16.10.2010, p. 8254-8260.

Research output: Contribution to journal › Article › peer-review

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AU - Masu, Hyuma

AU - Matsumura, Mio

AU - Yamaguchi, Kentaro

AU - Kagechika, Hiroyuki

AU - Tanatani, Aya

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