Issue 86, 2016

An efficient DFT method of predicting the one-, two- and three-bond indirect spin–spin coupling constants involving a fluorine nucleus in fluoroalkanes

Abstract

The values of the indirect nuclear spin–spin coupling constants for a series of aliphatic fluorocompounds have been calculated using DFT-based methods and compared with the experimental values of these parameters. The set of the molecular objects contained four fluoromethanes, five fluoroethanes, two fluorocyclopropanes, and eleven fluorocompounds containing either five-membered or six-membered rings. The effectiveness of three hybrid functionals, B3LYP, PBE0 and BHandH and three basis sets, 6-311++G(2d,p) (s), 6-311++G(3df,3pd) (m) and aug-pcJ-3-2006 (l) has been checked. In order to compare the results concerning various types of coupling constants and obtained by various methods, a prediction-quality criterion has been proposed. It has been found that only the BHandH functional ensures calculating the proper values of one-bond fluorine–carbon and two-bond fluorine–fluorine coupling constants. For this functional application of the s basis, the smallest of the bases tested, has already yielded acceptable good results. The DFT BHandH/s PCM method has also provided the proper values of nJ(F,H) (n = 1, 2, 3) and nJ(F,C) (n = 2, 3) parameters. On the other hand, the analysis of the limited number of the results concerning 1J(C,H) coupling constants has pointed out that in this case this method is less effective than the DFT PBE0/l PCM method.

Graphical abstract: An efficient DFT method of predicting the one-, two- and three-bond indirect spin–spin coupling constants involving a fluorine nucleus in fluoroalkanes

Supplementary files

Article information

Article type
Paper
Submitted
13 Jun 2016
Accepted
26 Aug 2016
First published
26 Aug 2016
This article is Open Access
Creative Commons BY license

RSC Adv., 2016,6, 82783-82792

An efficient DFT method of predicting the one-, two- and three-bond indirect spin–spin coupling constants involving a fluorine nucleus in fluoroalkanes

A. Gryff-Keller and P. Szczeciński, RSC Adv., 2016, 6, 82783 DOI: 10.1039/C6RA15343G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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