ChemInform Abstract: Rotational Photoisomerization of a Thioamide, N‐5‐Trifluoromethyl‐6‐methoxy‐1‐thionaphthoyl‐N‐methylglycine.

Shim, Sang Chul; Lee, S. J.

doi:10.1002/chin.198908096

Cited by 1 publication

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“…A thioamide has been shown to exhibit a higher C-N rotational barrier than a corresponding oxoamide, [41][42][43] and the C-N bond of thioamide can be isomerized by light irradiation. [44][45][46] Although experimental evidence has not been provided about the C-N bond rotation of selenoamide, a theoretical study also suggested that selenoamide will generate a more kinetically stable E/Z isomer. 43,47 On the other hand, there was no knowledge of the effect of chalcogen atoms on the C-C bond.…”

Section: Resultsmentioning

confidence: 99%

Photoinduced Concerted Dual Single-bond Rotation of a Nitrogen-containing System Realized by Chalcogen Substitution

Nagami

Katsuyama

Kaguchi

et al. 2022

Preprint

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Conformational change caused by photochemical concerted multiple bond rotation is a very rare event. Thus, it is a critical challenge to expand this chemistry because it has higher potential to more precisely modulate the molecular function of molecules. Here, we describe a novel nitrogen-containing molecular system exhibiting photoinduced concerted rotation, which is the first example of successfully incorporating heteroatoms into a system exhibiting photoinduced concerted rotation. Sufficient kinetic stability and photosensitivity to realize photoinduced concerted rotation can be brought to a sterically hindered benzamide system by chalcogen substitution. The photoinduced C-N/C-C concerted rotation of the thioamide derivative can be directly observed, and it was found that the thioamide system exhibits the ability to generate different conformers depending on external stimuli. A theoretical study also supported the selective occurrence of photoinduced C-N/C-C concerted rotation. It is expected that the system can be utilized to modulate the functions of organic compounds.

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Section: Resultsmentioning

confidence: 99%

Photoinduced Concerted Dual Single-bond Rotation of a Nitrogen-containing System Realized by Chalcogen Substitution

Nagami

Katsuyama

Kaguchi

et al. 2022

Preprint

View full text Add to dashboard Cite

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ChemInform Abstract: Rotational Photoisomerization of a Thioamide, N‐5‐Trifluoromethyl‐6‐methoxy‐1‐thionaphthoyl‐N‐methylglycine.

Abstract: The thioamide (I), which exerts aldose reductase inhibitory activity and is useful for the treatment of diabetic complications, undergoes trans‐cis photoisomerization in solution.

Cited by 1 publication

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Photoinduced Concerted Dual Single-bond Rotation of a Nitrogen-containing System Realized by Chalcogen Substitution

Photoinduced Concerted Dual Single-bond Rotation of a Nitrogen-containing System Realized by Chalcogen Substitution

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