Neighboring Chalcogen Bonding for Controlling Dynamic Imine Chemistry in Aqueous Media

被引：0
|
作者：
Zhou, Yong [1 ,2 ,3 ]
Zhang, Qinman [1 ,2 ,3 ]
Jia, Shuaipeng [2 ,4 ]
Ye, Hebo [2 ]
You, Lei [2 ,3 ]
机构：
[1] Fuzhou Univ, Coll Chem, Fuzhou 350108, Peoples R China
[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Peoples R China
[3] Univ Chinese Acad Sci, Fujian Coll, Fuzhou 350002, Peoples R China
[4] Quanzhou Normal Univ, Coll Chem Engn & Mat Sci, Quanzhou 362000, Peoples R China
来源：
ORGANIC LETTERS | 2025年 / 27卷 / 10期
基金：
中国国家自然科学基金;
关键词：
SCHIFF-BASE; COVALENT CHEMISTRY; MULTIVALENCY; CATALYSIS;
D O I：
10.1021/acs.orglett.5c00359
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The impact of varied chalcogen bonds (sulfur, selenium, tellurium, and telluronium) on dynamic imine chemistry in aqueous solution is presented by introducing a carboxylate group or cationic telluronium into arylaldehydes. The role of chalcogen bonding in regulating the kinetics and thermodynamics of imine formation/exchange was elucidated through experimental and computational evidence, affording the largest effect for tellurium/telluronium compounds. By leveraging multivalent chalcogen bonding, telluronium-containing aldehyde enabled labeling of the N-terminus of amino acids in neutral buffer.
引用
收藏
页码：2438 / 2443
页数：6
相关论文
共 50 条
  • [1] n → π* interactions as a versatile tool for controlling dynamic imine chemistry in both organic and aqueous media
    Chen, Hang
    Ye, Hebo
    Hai, Yu
    Zhang, Ling
    You, Lei
    CHEMICAL SCIENCE, 2020, 11 (10) : 2707 - 2715
  • [2] Chalcogen bonding in materials chemistry
    Ho, Peter C.
    Wang, Jin Z.
    Meloni, Francesca
    Vargas-Baca, Ignacio
    COORDINATION CHEMISTRY REVIEWS, 2020, 422
  • [3] Chalcogen bonding in coordination chemistry
    Mahmudov, Kamran T.
    Gurbanov, Atash V.
    Aliyeva, Vusala A.
    da Silva, M. Fatima C. Guedes
    Resnati, Giuseppe
    Pombeiro, Armando J. L.
    COORDINATION CHEMISTRY REVIEWS, 2022, 464
  • [4] Dynamic imine chemistry
    Belowich, Matthew E.
    Stoddart, J. Fraser
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (06) : 2003 - 2024
  • [5] Chemistry Evolves, Terms Evolve, but Phenomena Do Not Evolve: From Chalcogen-Chalcogen Interactions to Chalcogen Bonding
    Kolb, Simon
    Oliver, Gwyndaf A.
    Werz, Daniel B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (50) : 22306 - 22310
  • [6] Chiral halogen and chalcogen bonding receptors for discrimination of stereo- and geometric dicarboxylate isomers in aqueous media
    Lim, Jason Y. C.
    Marques, Igor
    Felix, Vitor
    Beer, Paul D.
    CHEMICAL COMMUNICATIONS, 2018, 54 (77) : 10851 - 10854
  • [7] RADIATION CHEMISTRY - AQUEOUS MEDIA
    HART, EJ
    SCIENCE, 1963, 141 (357) : 195 - &
  • [8] Dynamic imine chemistry in metal-organic polyhedra
    Vardhan, Harsh
    Mehta, Akshay
    Nath, Ipsita
    Verpoort, Francis
    RSC ADVANCES, 2015, 5 (82) : 67011 - 67030
  • [9] Associative and Thermoresponsive Aqueous Polymer Formulations Based on Imine Chemistry
    Crozzolo, Julien
    Formon, Georges J. M.
    Pomes-Hadda, Mickael
    Aime, Stefano
    Jouenne, Stephane
    Nicolay, Renaud
    ACS APPLIED POLYMER MATERIALS, 2022, 4 (06): : 4274 - 4285
  • [10] Dynamic Imine Chemistry at Complex Double Emulsion Interfaces
    Zentner, Cassandra A.
    Anson, Francesca
    Thayumanavan, S.
    Swager, Timothy M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (45) : 18048 - 18055
12345