In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid

S. Ohba; H. Hosomi; Y. Ito

doi:10.1021/ja0034287

In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid

S. Ohba, H. Hosomi, Y. Ito

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

124 Citations (Scopus)

Abstract

In the crystals of phthalic acid trans-cinnamamide (1:2), two molecules of cinnamamide are connected with phthalic acid via a hydrogen bond to form a three-component assembly. The C=C double bonds of two cinnamamides take a criss-crossed arrangement with a center-to-center distance of 4.252(3) Å and with a twist angle of 97.1(4)°. After a partial single-crystal-to-single-crystal transformation, X-ray analysis revealed the β-type photodimer of cinnamamide in the assembly at 13.2(3)% conversion. This suggests that the pedal-like conformational change occurred for one of the cinnamamide molecules and the C=C bond of the other cinnamamide moved approximately parallel to form a cyclobutane ring.

Original language	English
Pages (from-to)	6349-6352
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	123
Issue number	26
DOIs	https://doi.org/10.1021/ja0034287
Publication status	Published - 2001
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid",

abstract = "In the crystals of phthalic acid trans-cinnamamide (1:2), two molecules of cinnamamide are connected with phthalic acid via a hydrogen bond to form a three-component assembly. The C=C double bonds of two cinnamamides take a criss-crossed arrangement with a center-to-center distance of 4.252(3) {\AA} and with a twist angle of 97.1(4)°. After a partial single-crystal-to-single-crystal transformation, X-ray analysis revealed the β-type photodimer of cinnamamide in the assembly at 13.2(3)% conversion. This suggests that the pedal-like conformational change occurred for one of the cinnamamide molecules and the C=C bond of the other cinnamamide moved approximately parallel to form a cyclobutane ring.",

author = "S. Ohba and H. Hosomi and Y. Ito",

year = "2001",

doi = "10.1021/ja0034287",

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journal = "Journal of the American Chemical Society",

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T1 - In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid

AU - Ohba, S.

AU - Hosomi, H.

AU - Ito, Y.

PY - 2001

Y1 - 2001

N2 - In the crystals of phthalic acid trans-cinnamamide (1:2), two molecules of cinnamamide are connected with phthalic acid via a hydrogen bond to form a three-component assembly. The C=C double bonds of two cinnamamides take a criss-crossed arrangement with a center-to-center distance of 4.252(3) Å and with a twist angle of 97.1(4)°. After a partial single-crystal-to-single-crystal transformation, X-ray analysis revealed the β-type photodimer of cinnamamide in the assembly at 13.2(3)% conversion. This suggests that the pedal-like conformational change occurred for one of the cinnamamide molecules and the C=C bond of the other cinnamamide moved approximately parallel to form a cyclobutane ring.

AB - In the crystals of phthalic acid trans-cinnamamide (1:2), two molecules of cinnamamide are connected with phthalic acid via a hydrogen bond to form a three-component assembly. The C=C double bonds of two cinnamamides take a criss-crossed arrangement with a center-to-center distance of 4.252(3) Å and with a twist angle of 97.1(4)°. After a partial single-crystal-to-single-crystal transformation, X-ray analysis revealed the β-type photodimer of cinnamamide in the assembly at 13.2(3)% conversion. This suggests that the pedal-like conformational change occurred for one of the cinnamamide molecules and the C=C bond of the other cinnamamide moved approximately parallel to form a cyclobutane ring.

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In situ X-ray observation of pedal-like conformational change and dimerization of trans-cinnamamide in cocrystals with phthalic acid

Abstract

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