The mechanism of the excited-state multiple proton transfer reaction for 3-Me-2,6-diazaindole in aqueous solution

被引：16

作者：

Huang, Jin-Dou ^{[2
,3
]}

Ma, Huipeng ^{[1
]}

机构：

[1] Dalian Med Univ, Coll Med Lab Sci, Dalian 116044, Peoples R China

[2] Dalian Nationalities Univ, Sch Phys & Mat Engn, Key Lab Photosensit Mat & Devices Liaoning Prov, Key Lab New Energy & Rare Earth Resource Utilizat, Dalian 116600, Peoples R China

[3] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 18期

基金：

美国国家科学基金会;

关键词：

HYDROGEN-BONDING CATALYSTS; ASYMMETRIC CATALYSIS; LEWIS-ACID; CYCLOADDITION; KINETICS; DONORS;

D O I：

10.1039/c8qo00628h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The optical properties of 3-Me-2,6-diazaindole in aqueous solution were simulated and then found to compare well with experimental data. Furthermore, the ground state and exited state potential energy surfaces for 3-Me-2,6-diazaindole + L3H(2)O were constructed, and a new three water molecules-assisted exited state quadruple proton transfer mechanism is proposed.

引用

页码：2749 / 2753

页数：5

共 21 条

[1] Toward reliable density functional methods without adjustable parameters: The PBE0 model [J].

Adamo, C ;

Barone, V .

JOURNAL OF CHEMICAL PHYSICS, 1999, 110 (13) :6158-6170

[2]

[Anonymous], 2017, COMMUN COMPUT CHEM, DOI DOI 10.4208/cicc.2017.v5.n2.1

[3] PyBidine-Cu(OTf)2-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu-Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis [J].

Arai, Takayoshi ;

Ogawa, Hiroki ;

Awata, Atsuko ;

Sato, Makoto ;

Watabe, Megumi ;

Yamanaka, Masahiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1595-1599

[4] Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis [J].

Banik, Steven M. ;

Levina, Anna ;

Hyde, Alan M. ;

Jacobsen, Eric N. .

SCIENCE, 2017, 358 (6364) :761-764

[5] Tracking Reactive Water and Hydrogen-Bonding Networks in Photosynthetic Oxygen Evolution [J].

Barry, Bridgette A. ;

Brahmachari, Udita ;

Guo, Zhanjun .

ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (08) :1937-1945

[6] Direct Synthesis of Symmetrical Azines from Alcohols and Hydrazine Catalyzed by a Ruthenium Pincer Complex: Effect of Hydrogen Bonding [J].

Bauer, Jonathan O. ;

Leitus, Gregory ;

Ben-David, Yehoshoa ;

Milstein, David .

ACS CATALYSIS, 2016, 6 (12) :8415-8419

[7] Asymmetric Hydrogen Bonding Catalysis for the Synthesis of Dihydroquinazoline-Containing Antiviral, Letermovir [J].

Chung, Cheol K. ;

Liu, Zhijian ;

Lexa, Katrina W. ;

Andreani, Teresa ;

Xu, Yingju ;

Ji, Yining ;

DiRocco, Daniel A. ;

Humphrey, Guy R. ;

Ruck, Rebecca T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) :10637-10640

[8] The Excited-State Triple Proton Transfer Reaction of 2,6-Diazaindoles and 2,6-Diazatryptophan in Aqueous Solution [J].

Chung, Kun-You ;

Chen, Yi-Han ;

Chen, Yi-Ting ;

Hsu, Yen-Hao ;

Shen, Jiun-Yi ;

Chen, Chi-Lin ;

Chen, Yi-An ;

Chou, Pi-Tai .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (18) :6396-6402

[9] Reaction Progress Kinetics Analysis of 1,3-Disiloxanediols as Hydrogen-Bonding Catalysts [J].

Diemoz, Kayla M. ;

Hein, Jason E. ;

Wilson, Sean O. ;

Fettinger, James C. ;

Franz, Annaliese K. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13) :6738-6747

[10] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

← 1 2 3 →