Premium
15 N and 13 C NMR chemical shifts of 6‐(fluoro, chloro, bromo, and iodo)purine 2′‐deoxynucleosides: measurements and calculations
Author(s) -
Bai Shi,
Dmitrenko Olga,
Dybowski Cecil
Publication year - 2010
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2541
Subject(s) - chemistry , chemical shift , density functional theory , computational chemistry , halogen , context (archaeology) , solvation , coupling constant , carbon 13 nmr , stereochemistry , organic chemistry , molecule , paleontology , alkyl , physics , particle physics , biology
The 15 N and 13 C chemical shifts of 6‐(fluoro, chloro, bromo, and iodo)purine 2′‐deoxynucleoside derivatives in deuterated chloroform were measured. The 15 N chemical shifts were determined by the 1 H 15 N HMBC method, and complete 15 N chemical‐shift assignments were made with the aid of density functional theory (DFT) calculations. Inclusion of solvation effects significantly improved the precision of the calculations of 15 N chemical shifts. Halogen‐substitution effects on the 15 N and 13 C chemical shifts of purine rings are discussed in the context of DFT results. The experimental coupling constants for 19 F interacting with 15 N and 13 C of the 6‐fluoropurine 2‐deoxynuleoside are compared with those from DFT calculations. Copyright © 2009 John Wiley & Sons, Ltd.