Compelled orientational control of the solid-state photodimerization of trans-cinnamamides: Dicarboxylic acid as a non-covalent linker

Yoshikatsu Ito, Hiroyuki Hosomi, Shigeru Ohba

研究成果: Article

62 引用 (Scopus)

抄録

The 2:1 hydrogen-bonded cocrystals 1a·ox, la·su, 1a·pht, 1a·fu, 1b·ox, 1c·ox, 1d·ox between trans-cinnamamides (1a-1d) and dicarboxylic acids (ox, su, gl, fu, pht) were prepared and characterized by IR and powder X-ray techniques. The crystal structures of 1a·pht, 1a·ox and 1a·fu were solved by single crystal X-ray diffraction. Phthalic acid (pht) caused β-type photodimerization of trans-cinnamamide (1a) in the cocrystal and functioned as a non-covalent linker like gauche 1,2-diamines in photodimerization of trans-cinnamic acids. Oxalic acid (ox) enforced 1a to take a bilayer structure that is suitable for β-type photodimerization. In the case of fumaric acid (fu), cross photodimerization with 1a occurred to give a cycloadduct 4. For the cocrystals 1a·pht and 1a·fu, pedal-like motion was assumed to occur prior to the dimerization. (C) 2000 Elsevier Science Ltd.

元の言語English
ページ(範囲)6833-6844
ページ数12
ジャーナルTetrahedron
56
発行部数36
出版物ステータスPublished - 2000

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Oxalic Acid
Dicarboxylic Acids
Diamines
Dimerization
X-Ray Diffraction
Powders
Foot
Hydrogen
Crystal structure
X-Rays
Single crystals
X ray diffraction
X rays
phthalic acid
fumaric acid
cinnamamide
cinnamic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

これを引用

Compelled orientational control of the solid-state photodimerization of trans-cinnamamides : Dicarboxylic acid as a non-covalent linker. / Ito, Yoshikatsu; Hosomi, Hiroyuki; Ohba, Shigeru.

:: Tetrahedron, 巻 56, 番号 36, 2000, p. 6833-6844.

研究成果: Article

Ito, Yoshikatsu ; Hosomi, Hiroyuki ; Ohba, Shigeru. / Compelled orientational control of the solid-state photodimerization of trans-cinnamamides : Dicarboxylic acid as a non-covalent linker. :: Tetrahedron. 2000 ; 巻 56, 番号 36. pp. 6833-6844.
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T1 - Compelled orientational control of the solid-state photodimerization of trans-cinnamamides

T2 - Dicarboxylic acid as a non-covalent linker

AU - Ito, Yoshikatsu

AU - Hosomi, Hiroyuki

AU - Ohba, Shigeru

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N2 - The 2:1 hydrogen-bonded cocrystals 1a·ox, la·su, 1a·pht, 1a·fu, 1b·ox, 1c·ox, 1d·ox between trans-cinnamamides (1a-1d) and dicarboxylic acids (ox, su, gl, fu, pht) were prepared and characterized by IR and powder X-ray techniques. The crystal structures of 1a·pht, 1a·ox and 1a·fu were solved by single crystal X-ray diffraction. Phthalic acid (pht) caused β-type photodimerization of trans-cinnamamide (1a) in the cocrystal and functioned as a non-covalent linker like gauche 1,2-diamines in photodimerization of trans-cinnamic acids. Oxalic acid (ox) enforced 1a to take a bilayer structure that is suitable for β-type photodimerization. In the case of fumaric acid (fu), cross photodimerization with 1a occurred to give a cycloadduct 4. For the cocrystals 1a·pht and 1a·fu, pedal-like motion was assumed to occur prior to the dimerization. (C) 2000 Elsevier Science Ltd.

AB - The 2:1 hydrogen-bonded cocrystals 1a·ox, la·su, 1a·pht, 1a·fu, 1b·ox, 1c·ox, 1d·ox between trans-cinnamamides (1a-1d) and dicarboxylic acids (ox, su, gl, fu, pht) were prepared and characterized by IR and powder X-ray techniques. The crystal structures of 1a·pht, 1a·ox and 1a·fu were solved by single crystal X-ray diffraction. Phthalic acid (pht) caused β-type photodimerization of trans-cinnamamide (1a) in the cocrystal and functioned as a non-covalent linker like gauche 1,2-diamines in photodimerization of trans-cinnamic acids. Oxalic acid (ox) enforced 1a to take a bilayer structure that is suitable for β-type photodimerization. In the case of fumaric acid (fu), cross photodimerization with 1a occurred to give a cycloadduct 4. For the cocrystals 1a·pht and 1a·fu, pedal-like motion was assumed to occur prior to the dimerization. (C) 2000 Elsevier Science Ltd.

KW - Cinnamamides

KW - Cocrystals

KW - Dicarboxylic acids

KW - Dynamic disorder

KW - Hydrogen bond

KW - Solid-state photodimerization

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