Study of H/D exchange rates to derive the strength of intramolecular hydrogen bonds in halo substituted organic building blocks: An NMR spectroscopic investigation

被引:8
作者
Mishra, Sundeep Kumar
Suryaprakash, N. [1 ]
机构
[1] Indian Inst Sci, NMR Res Ctr, Bangalore 560012, Karnataka, India
关键词
ASYMMETRIC CATALYSIS; DEUTERIUM-EXCHANGE; BASE-PAIRS; PEPTIDOMIMETICS; PEPTIDES; DESIGN; MECHANISM; NETWORKS; SYSTEMS; AMIDES;
D O I
10.1016/j.cplett.2015.09.038
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
Rates of hydrogen/deuterium (H/D) exchange determined by H-1 NMR spectroscopy are utilized to derive the strength of hydrogen bonds and to monitor the electronic effects in the site-specific halogen substituted benzamides and anilines. The theoretical fitting of the time dependent variation of the integral areas of H-1 NMR resonances to the first order decay function permitted the determination of HID exchange rate constants (k) and their precise half-lives (t(1/2)) with high degree of reproducibility. The comparative study also permitted the unambiguous determination of relative strength of hydrogen bonds and the contribution from electronic effects on the HID exchange rate. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:254 / 260
页数:7
相关论文
共 48 条
[1]   Water Scaffolding in Collagen: Implications on Protein Dynamics as Revealed by Solid-State NMR [J].
Aliev, Abil E. ;
Courtier-Murias, Denis .
BIOPOLYMERS, 2014, 101 (03) :246-256
[2]   Bioinspired dual self-folding of single polymer chains via reversible hydrogen bonding [J].
Altintas, Ozcan ;
Lejeune, Elise ;
Gerstel, Peter ;
Barner-Kowollik, Christopher .
POLYMER CHEMISTRY, 2012, 3 (03) :640-651
[3]   Regioselective Reactivity of an Asymmetric Tetravalent Di[dihydroxotin(IV)] Bis-Porphyrin Host Driven by Hydrogen-Bond Templation [J].
Brotherhood, Peter R. ;
Luck, Ian J. ;
Blake, Iain M. ;
Jensen, Paul ;
Turner, Peter ;
Crossley, Maxwell J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (35) :10967-10977
[4]   Evolution of Dynamic Combinatorial Chemistry [J].
Cougnon, Fabien B. L. ;
Sanders, Jeremy K. M. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (12) :2211-2221
[5]   Internucleotide scalar couplings across hydrogen bonds in Watson-Crickand Hoogsteen base pairs of a DNA triplex [J].
Dingley, AJ ;
Masse, JE ;
Peterson, RD ;
Barfield, M ;
Feigon, J ;
Grzesiek, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) :6019-6027
[6]   Substituent Effects on Energetics of Peptide-Carboxylate Hydrogen Bonds as Studied by 1H NMR Spectroscopy: Implications for Enzyme Catalysis [J].
Emenike, Bright U. ;
Liu, Albert Tianxiang ;
Naveo, Elsy P. ;
Roberts, John D. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23) :11765-11771
[7]  
Furniss B.S., 1989, Textbook of Practical Organic Chemistry
[8]   Design and synthesis of regioisomeric triazole based peptidomimetic macrocycles and their dipole moment controlled self-assembly [J].
Ghorai, Abhijit ;
Padmanaban, E. ;
Mukhopadhyay, Chaitali ;
Achari, Basudeb ;
Chattopadhyay, Partha .
CHEMICAL COMMUNICATIONS, 2012, 48 (98) :11975-11977
[9]   Foldamers as versatile frameworks for the design and evolution of function [J].
Goodman, Catherine M. ;
Choi, Sungwook ;
Shandler, Scott ;
DeGrado, William F. .
NATURE CHEMICAL BIOLOGY, 2007, 3 (05) :252-262
[10]   Asymmetric Catalysis at the Mesoscale: Gold Nanoclusters Embedded in Chiral Self-Assembled Monolayer as Heterogeneous Catalyst for Asymmetric Reactions [J].
Gross, Elad ;
Liu, Jack H. ;
Alayoglu, Selim ;
Marcus, Matthew A. ;
Fakra, Sirine C. ;
Toste, F. Dean ;
Somorjai, Gabor A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (10) :3881-3886