Resonance-Assisted Hydrogen Bonding as a Driving Force in Synthesis and a Synthon in the Design of Materials

被引：153
作者：
Mahmudov, Kamran T. [1 ,2 ]
Pombeiro, Armando J. L. [1 ]
机构：
[1] Univ Lisbon, Inst Super Tecn, Ctr Quim Estrutural, Ave Rovisco Pais, P-1049001 Lisbon, Portugal
[2] Baku State Univ, Dept Chem, Z Xalilov Str 23, AZ-1148 Baku, Azerbaijan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 46期
关键词：
conjugation; crystal engineering; hydrogen bonds; pi interactions; synthetic methods; INTRAMOLECULAR PROTON-TRANSFER; CENTER-DOT-O; TEMPERATURE X-RAY; AB-INITIO CALCULATIONS; KETO-ENOL-TAUTOMERISM; SOLID-STATE; CRYSTAL-STRUCTURE; BETA-DIKETONES; SCHIFF-BASES; RATIOMETRIC DETECTION;
D O I：
10.1002/chem.201601766
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Resonance-assisted hydrogen bonding (RAHB), a concept introduced by Gilli and co-workers in 1989, concerns a kind of intramolecular H-bonding strengthened by a conjugated -system, usually in 6-, 8-, or 10-membered rings. This Review highlights the involvement of RAHB as a driving force in the synthesis of organic, coordination, and organometallic compounds, as a handy tool in the activation of covalent bonds, and in starting moieties for synthetic transformations. The unique roles of RAHB in molecular recognition and switches, E/Z isomeric resolution, racemization and epimerization of amino acids and chiral amino alcohols, solvatochromism, liquid-crystalline compounds, and in synthons for crystal engineering and polymer materials are also discussed. The Review can provide practical guidance for synthetic chemists that are interested in exploring and further developing RAHB-assisted synthesis and design of materials.
引用
收藏
页码：16356 / 16398
页数：43
相关论文
共 371 条
[51]   Synthesis and crystal structure of 2,4-dihydro-4-[(5-hydroxy-3methyl-1-phenyl-1H-pyrazol-4-yl)imino]-5-methyl-2-phenyl-3H-pyrazol-3-one and its copper(II) complex [J].
Cerchiaro, Giselle ;
Da Costa Ferreira, Ana M. ;
Teixeira, Aline B. ;
Magalhaes, Hugo M. ;
Cunha, Anna C. ;
Ferreira, Vitor F. ;
Santos, Leonardo S. ;
Eberlin, Marcos N. ;
Skakle, Janet M. S. ;
Wardell, Solange M. S. V. ;
Wardell, James L. .
POLYHEDRON, 2006, 25 (10) :2055-2064
[52]   Tuning steric and electronic effects in transition-metal β-diketiminate complexes [J].
Chen, Chi ;
Bellows, Sarina M. ;
Holland, Patrick L. .
DALTON TRANSACTIONS, 2015, 44 (38) :16654-16670
[53]   In search of the weak, six-membered intramolecular hydrogen bond in the solution and solid states of guanidinobenzimidazole [J].
Chen, J ;
Willis, PG ;
Parkin, S ;
Cammers, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (01) :171-178
[54]   Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding [J].
Chin, J ;
Kim, DC ;
Kim, HJ ;
Panosyan, FB ;
Kim, KM .
ORGANIC LETTERS, 2004, 6 (15) :2591-2593
[55]   Controlling diaza-cope rearrangement reactions with resonance-assisted hydrogen bonds [J].
Chin, J ;
Mancin, F ;
Thavarajah, N ;
Lee, DY ;
Lough, A ;
Chung, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15276-15277
[56]  
Chin J., 2014, EUR J ORG CHEM, V725
[57]   Derivatives of 1-phenyl-3-methylpyrazol-2-in-5-thione and their oxygen analogues in the crystalline phase and their tautomeric transformations in solutions and in the gas phase [J].
Chmutova, GA ;
Kataeva, ON ;
Ahlbrecht, H ;
Kurbangalieva, AR ;
Movchan, AI ;
Lenstra, ATH ;
Geise, HJ .
JOURNAL OF MOLECULAR STRUCTURE, 2001, 570 (1-3) :215-223
[58]   Quenching of Fluorescence in Bodipy-Derived Trifluoromethyl Enaminone Ligands upon Coordination to Copper(II) [J].
Chopin, Nicolas ;
Medebielle, Maurice ;
Maury, Olivier ;
Novitchi, Ghenadie ;
Pilet, Guillaume .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, (36) :6185-6195
[59]   A polymeric colorimetric sensor with excited-state intramolecular proton transfer for anionic species [J].
Chu, Qinghui ;
Medvetz, Doug A. ;
Pang, Yi .
CHEMISTRY OF MATERIALS, 2007, 19 (26) :6421-6429
[60]  
Claramunt RM, 2001, ANGEW CHEM INT EDIT, V40, P420, DOI 10.1002/1521-3773(20010119)40:2<420::AID-ANIE420>3.0.CO
12345678910