Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: Dual activated 1,2-hydride shift mechanism by protonated Al(OH) 3 species

Takashi Ohshima; Yoshihiro Yamamoto; Usaji Takaki; Yoshihisa Inoue; Takuya Saeki; Kenji Itou; Yusuke Maegawa; Takanori Iwasaki; Kazushi Mashima

doi:10.1039/b902729g

Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: Dual activated 1,2-hydride shift mechanism by protonated Al(OH) ₃ species

Takashi Ohshima, Yoshihiro Yamamoto, Usaji Takaki, Yoshihisa Inoue, Takuya Saeki, Kenji Itou, Yusuke Maegawa, Takanori Iwasaki, Kazushi Mashima

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

9 Citations (Scopus)

Abstract

Density functional theory calculations demonstrate that Al(iii)-catalyzed conversion of glyoxal to glycolic acid proceeds via a 7-membered dual Lewis acid-hydrogen bonding activation transition state of the 1,2-hydride shift, rather than the previously proposed 5-membered metal-alkoxide chelate activation transition state.

Original language	English
Pages (from-to)	2688-2690
Number of pages	3
Journal	Chemical Communications
Issue number	19
DOIs	https://doi.org/10.1039/b902729g
Publication status	Published - 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/b902729g

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title = "Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: Dual activated 1,2-hydride shift mechanism by protonated Al(OH) 3 species",

abstract = "Density functional theory calculations demonstrate that Al(iii)-catalyzed conversion of glyoxal to glycolic acid proceeds via a 7-membered dual Lewis acid-hydrogen bonding activation transition state of the 1,2-hydride shift, rather than the previously proposed 5-membered metal-alkoxide chelate activation transition state.",

author = "Takashi Ohshima and Yoshihiro Yamamoto and Usaji Takaki and Yoshihisa Inoue and Takuya Saeki and Kenji Itou and Yusuke Maegawa and Takanori Iwasaki and Kazushi Mashima",

year = "2009",

doi = "10.1039/b902729g",

language = "English",

pages = "2688--2690",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid

T2 - Dual activated 1,2-hydride shift mechanism by protonated Al(OH) 3 species

AU - Ohshima, Takashi

AU - Yamamoto, Yoshihiro

AU - Takaki, Usaji

AU - Inoue, Yoshihisa

AU - Saeki, Takuya

AU - Itou, Kenji

AU - Maegawa, Yusuke

AU - Iwasaki, Takanori

AU - Mashima, Kazushi

PY - 2009

Y1 - 2009

N2 - Density functional theory calculations demonstrate that Al(iii)-catalyzed conversion of glyoxal to glycolic acid proceeds via a 7-membered dual Lewis acid-hydrogen bonding activation transition state of the 1,2-hydride shift, rather than the previously proposed 5-membered metal-alkoxide chelate activation transition state.

AB - Density functional theory calculations demonstrate that Al(iii)-catalyzed conversion of glyoxal to glycolic acid proceeds via a 7-membered dual Lewis acid-hydrogen bonding activation transition state of the 1,2-hydride shift, rather than the previously proposed 5-membered metal-alkoxide chelate activation transition state.

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U2 - 10.1039/b902729g

DO - 10.1039/b902729g

M3 - Article

C2 - 19532922

AN - SCOPUS:65549100074

SN - 1359-7345

SP - 2688

EP - 2690

JO - Chemical Communications

JF - Chemical Communications

IS - 19

ER -

Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: Dual activated 1,2-hydride shift mechanism by protonated Al(OH) ₃ species

Abstract

All Science Journal Classification (ASJC) codes

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