The role of synergic interaction in transition state formation for the aldol reaction on a metal oxide catalyst: a DFT investigation

被引：19

作者：

An, Wei ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, Shanghai 201620, Peoples R China

来源：

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | 2015年 / 17卷 / 35期

关键词：

ACYCLIC STEREOSELECTION; CONDENSATIONS; ACETALDEHYDE; GENERATION; ADDITIONS;

D O I：

10.1039/c5cp03478g

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

This contribution highlights an eight-membered ring transition state for the aldol reaction of propanal on O-terminated ZrO2(111) and CeO2(111) surfaces. The relative heights of activation barriers for a-H abstraction and nucleophilic addition are controlled by surface acid-base pair strength. We report the first theoretical evidence of an alternative to the Zimmerman-Traxler model.

引用

页码：22529 / 22532

页数：4

共 25 条

[1] Oxygen Vacancy-Assisted Coupling and Enolization of Acetaldehyde on CeO2(111) [J].

Calaza, Florencia C. ;

Xu, Ye ;

Mullins, David R. ;

Overbury, Steven H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (43) :18034-18045

[2] METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION [J].

CARREIRA, EM ;

SINGER, RA .

TETRAHEDRON LETTERS, 1994, 35 (25) :4323-4326

[3] Solid Nanoparticles that Catalyze Biofuel Upgrade Reactions at the Water/Oil Interface [J].

Crossley, Steven ;

Faria, Jimmy ;

Shen, Min ;

Resasco, Daniel E. .

SCIENCE, 2010, 327 (5961) :68-72

[4] Asymmetric catalysis of aldol reactions with chiral Lewis bases [J].

Denmark, SE ;

Stavenger, RA .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :432-440

[5] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

VOGEL, E ;

NELSON, JV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) :6120-6123

[6] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

[7] ON THE ORIGIN OF PI-FACIAL DIASTEREOSELECTIVITY IN NUCLEOPHILIC ADDITIONS TO CHIRAL CARBONYL-COMPOUNDS .1. ROTATIONAL PROFILES OF PROPIONALDEHYDE-1, CHLOROACETALDEHYDE-2, AND 2-CHLOROPROPIONALDEHYDE-3 [J].

FRENKING, G ;

KOHLER, KF ;

REETZ, MT .

TETRAHEDRON, 1991, 47 (43) :8991-9004

[8] Condensation reactions of propanal over CexZr1-xO2 mixed oxide catalysts [J].

Gangadharan, Anirudhan ;

Shen, Min ;

Sooknoi, Tawan ;

Resasco, Daniel E. ;

Mallinson, Richard G. .

APPLIED CATALYSIS A-GENERAL, 2010, 385 (1-2) :80-91

[9] Experimental and Theoretical Study of n-Butanal Self-Condensation over Ti Species Supported on Silica [J].

Hanna, David G. ;

Shylesh, Sankaranarayanapillai ;

Li, Yi-Pei ;

Krishna, Siddarth ;

Head-Gordon, Martin ;

Bell, Alexis T. .

ACS CATALYSIS, 2014, 4 (09) :2908-2916

[10] ACYCLIC STEREOSELECTION .36. SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOL SILANES WITH ALDEHYDES [J].

HEATHCOCK, CH ;

DAVIDSEN, SK ;

HUG, KT ;

FLIPPIN, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3027-3037

← 1 2 3 →