13C NMR Chemical Shift Assignments of Nitrated Benzo[a]pyrenes Based on Two-dimensional Techniques and DFT/GIAO Calculations
Document Type
Article
Publication Date
Spring 1-6-2021
Publication Title
Results in Chemistry
Abstract
Nitrated benzo[a]pyrenes are known to be mutagenic, carcinogenic and teratogenic to bacterial and animal cells. For differentiation of isomers and environmental analytical trace studies, spectroscopic information is necessary. The present studies report the 13C NMR spectra of 1‐,3‐and 6‐nitrobenzo[a]pyrene measured in CDCl3. Complete 13C NMR assignments based on 2D NMR spectroscopy (HMQC and HMBC) were carried out. Further, the computation of fifty 13C chemical shifts of 1‐, 3‐, and 6‐nitrobenzo[a]pyrenes by using GIAO B3LYP/6‐311+G(d,p)//B3LYP/6‐31+G(d), 6‐31+G(d,p), 6‐311+G(d), 6‐311+G(d,p), 6‐311G(d,p) levels of theory was investigated. For 1‐,3‐ and 6‐NBaP the calculated chemical shifts δcalc versus δexpt plots of chemical shifts fall on a linear correlation line with r2> 0.90. The GIAO B3LYP/6‐311+G(d,p)//B3LYP/6‐311G(d,p) level of theory was found to yield chemical shifts in good agreement with experiment with r2> 0.90. The most expensive method (larger basis set) has provided the best agreement with the experiment. It is therefore important to continue to seek computational methods that can predict precise chemical shifts in nitrated or related compounds.
Volume
3
DOI
https://doi.org/10.1016/j.rechem.2021.100099
ISSN
2211-7156
Repository Citation
Onchoke, Kefa Karimu, "13C NMR Chemical Shift Assignments of Nitrated Benzo[a]pyrenes Based on Two-dimensional Techniques and DFT/GIAO Calculations" (2021). Faculty Publications. 95.
https://scholarworks.sfasu.edu/chemistry_facultypubs/95
Comments
Simulated 13C NMR chemical shifts were calculated using DFT method with Pople-type basis sets and correlated with experimental peaks.